WRMK / Watermark Lodging Trust Inc - Class A - SEC फाइलिंग, वार्षिक रिपोर्ट, प्रॉक्सी स्टेटमेंट

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CIK 1609471
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Watermark Lodging Trust Inc - Class A
SEC Filings (Chronological Order)
यह पृष्ठ SEC फाइलिंग की एक पूरी, कालानुक्रमिक सूची प्रदान करता है, ओनरशिप फाइलिंग को छोड़कर, जो हम अन्यत्र प्रदान करते हैं।
October 21, 2022 15-12G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 15 CERTIFICATION AND NOTICE OF TERMINATION OF REGISTRATION UNDER SECTION 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 OR SUSPENSION OF DUTY TO FILE REPORTS UNDER SECTIONS 13

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 15 CERTIFICATION AND NOTICE OF TERMINATION OF REGISTRATION UNDER SECTION 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 OR SUSPENSION OF DUTY TO FILE REPORTS UNDER SECTIONS 13 AND 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. Commission File Number 000-55461 WATERMARK LODGING TRUST, INC. (Exact name of registrant as specifi

October 20, 2022 S-8 POS

As filed with the Securities and Exchange Commission on October 20, 2022

As filed with the Securities and Exchange Commission on October 20, 2022 Registration No.

October 20, 2022 S-8 POS

As filed with the Securities and Exchange Commission on October 20, 2022

S-8 POS 1 tm2228607d2s8pos.htm S-8 POS As filed with the Securities and Exchange Commission on October 20, 2022 Registration No. 333-250933 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 POST-EFFECTIVE AMENDMENT NO. 1 TO Form S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 WATERMARK LODGING TRUST, INC. (Exact name of registrant as specified in its charter) Mary

October 20, 2022 S-3DPOS

As filed with the Securities and Exchange Commission on October 20, 2022

As filed with the Securities and Exchange Commission on October 20, 2022 Registration No.

September 12, 2022 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): September 9, 2022 WATERMARK LODGING TRUST, INC. (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 (Commission Fi

September 12, 2022 EX-99.1

Watermark Lodging Trust Announces Stockholder Approval of Acquisition by Brookfield Transaction Provides Cash Liquidity for Watermark Lodging Trust Stockholders

Exhibit 99.1 Watermark Lodging Trust Announces Stockholder Approval of Acquisition by Brookfield Transaction Provides Cash Liquidity for Watermark Lodging Trust Stockholders Chicago, September 12, 2022 ? Watermark Lodging Trust, Inc. (?Watermark,? ?WLT? or the ?Company?) today announced that, at a Special Meeting of Stockholders, the proposed acquisition of WLT by private real estate funds managed

September 2, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Defin

August 25, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     ) Filed by the Registrant  x Filed by a Party other than the Registrant  ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ¨

August 17, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ????) Filed by the Registrant??x Filed by a Party other than the Registrant??? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ?

August 11, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2022 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 WATERMARK LODGING TRU

August 11, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ????) Filed by the Registrant??x Filed by a Party other than the Registrant??? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ?

July 29, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     )

DEFA14A 1 tm2219804d4defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     ) Filed by the Registrant  x Filed by a Party other than the Registrant  ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission

July 19, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     )

DEFA14A 1 tm2219804d1defa14.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     ) Filed by the Registrant  x Filed by a Party other than the Registrant  ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission O

July 15, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     )

DEFA14A 1 tm2219804d3defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     ) Filed by the Registrant  x Filed by a Party other than the Registrant  ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission

July 11, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     )

DEFA14A 1 tm2220748d1defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     ) Filed by the Registrant  x Filed by a Party other than the Registrant  ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission

June 24, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 17, 2022 WATERMARK LODGING TRUST, INC. (Exact name of registrant as specified in its charter) Maryland (State or other jurisdiction of incorporation) 000-55461 (Commission File N

June 24, 2022 EX-10.1

Incorporated by reference to Exhibit 10.1 to Current Report on Form 8-K, filed on June 24, 2022

Exhibit 10.1 Execution Certain confidential information contained in this document, marked by [***], has been omitted pursuant to Item 601(b)(10)(iv) of Regulation S-K because it is both (i) not material and (ii) is the type that the registrant customarily and actually treats as private or confidential. WATERMARK LODGING TRUST, INC. AMENDED AND RESTATED EMPLOYEE RETENTION AND SEVERANCE PLAN This A

June 24, 2022 EX-10.2

Amended and Restated Employment Agreement, dated June 21, 2022, between Watermark Lodging Trust, Inc. and Michael G. Medzigian.*

Exhibit 10.2 Execution Certain confidential information contained in this document, marked by [***], has been omitted pursuant to Item 601(b)(10)(iv) of Regulation S-K because it is both (i) not material and (ii) is the type that the registrant customarily and actually treats as private or confidential. AMENDED AND RESTATED EMPLOYMENT AGREEMENT AMENDED AND RESTATED EMPLOYMENT AGREEMENT (the “Amend

June 22, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     ) Filed by the Registrant  x Filed by a Party other than the Registrant  ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ¨

June 16, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     )

DEFA14A 1 tm223444d8defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     ) Filed by the Registrant  x Filed by a Party other than the Registrant  ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission O

June 15, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     )

DEFA14A 1 tm223444d5defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     ) Filed by the Registrant  x Filed by a Party other than the Registrant  ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission O

June 15, 2022 DEFM14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

June 15, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     )

DEFA14A 1 tm223444d6defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     ) Filed by the Registrant  x Filed by a Party other than the Registrant  ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission O

June 15, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.     )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ????) Filed by the Registrant??x Filed by a Party other than the Registrant??? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ?

May 27, 2022 PREM14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

May 27, 2022 EX-FILING FEES

Calculation of Filing Fee Tables SCHEDULE 14A (Form Type) Watermark Lodging Trust, Inc. (Name of registrant as specified in its charter) Table 1: Transaction Value

Exhibit Fee Tables Calculation of Filing Fee Tables SCHEDULE 14A (Form Type) Watermark Lodging Trust, Inc.

May 12, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 WATERMARK LODGING TR

May 9, 2022 EX-2.1

Incorporated by reference to Exhibit 2.1 to Current Report on Form 8-K, filed on May 9, 2022

Exhibit 2.1 EXECUTION VERSION AGREEMENT AND PLAN OF MERGER DATED AS OF MAY 6, 2022 BY AND AMONG Watermark Lodging Trust, INC., CWI 2 OP, LP, The Parent Entities Named Herein, Ruby Merger Sub I LLC AND Ruby Merger Sub II LP TABLE OF CONTENTS Page Article I THE MERGERS 2 Section 1.1. The Mergers 2 Section 1.2. Governing Documents 2 Section 1.3. Officers, General Partner and Limited Partners of the S

May 9, 2022 EX-2.1

Agreement and Plan of Merger, dated as of May 6, 2022, by and among Watermark Lodging Trust, Inc., the Parent Entities named therein, Ruby Merger Sub I LLC, Ruby Merger Sub II LP, and CWI 2 OP, LP.*

Exhibit 2.1 EXECUTION VERSION AGREEMENT AND PLAN OF MERGER DATED AS OF MAY 6, 2022 BY AND AMONG Watermark Lodging Trust, INC., CWI 2 OP, LP, The Parent Entities Named Herein, Ruby Merger Sub I LLC AND Ruby Merger Sub II LP TABLE OF CONTENTS Page Article I THE MERGERS 2 Section 1.1. The Mergers 2 Section 1.2. Governing Documents 2 Section 1.3. Officers, General Partner and Limited Partners of the S

May 9, 2022 EX-99.2

Letter from Watermark Lodging Trust, Inc. to stockholders.

Exhibit 99.2 May 6, 2022 Dear Fellow Shareholder, We are pleased to announce that Watermark Lodging Trust, Inc. (?WLT?) has entered into a definitive merger agreement with private real estate funds managed by Brookfield ("Brookfield"). Under the terms of the agreement, Brookfield will acquire all of the outstanding common shares of WLT for $6.768 per Class A share and $6.699 per Class T share in a

May 9, 2022 EX-99.1

Press release issued on May 6, 2022.

EX-99.1 3 tm2214819d2ex99-1.htm EXHIBIT 99.1 Exhibit 99.1 Watermark Lodging Trust to be Acquired by Brookfield Real Estate Funds $3.8 Billion All-Cash Transaction Provides Liquidity for Watermark Lodging Trust Stockholders Chicago, May 6, 2022 – Watermark Lodging Trust, Inc. (“Watermark,” “WLT” or the “Company”) announced today that it has entered into a definitive agreement with private real esta

May 9, 2022 EX-99.2

Watermark Lodging Trust, Inc. | 150 North Riverside Plaza, Suite 4200, Chicago, IL 60606 | 1-855-WLT REIT (958-7348)

Exhibit 99.2 May 6, 2022 Dear Fellow Shareholder, We are pleased to announce that Watermark Lodging Trust, Inc. (?WLT?) has entered into a definitive merger agreement with private real estate funds managed by Brookfield ("Brookfield"). Under the terms of the agreement, Brookfield will acquire all of the outstanding common shares of WLT for $6.768 per Class A share and $6.699 per Class T share in a

May 9, 2022 EX-99.1

Watermark Lodging Trust to be Acquired by Brookfield Real Estate Funds $3.8 Billion All-Cash Transaction Provides Liquidity for Watermark Lodging Trust Stockholders

Exhibit 99.1 Watermark Lodging Trust to be Acquired by Brookfield Real Estate Funds $3.8 Billion All-Cash Transaction Provides Liquidity for Watermark Lodging Trust Stockholders Chicago, May 6, 2022 – Watermark Lodging Trust, Inc. (“Watermark,” “WLT” or the “Company”) announced today that it has entered into a definitive agreement with private real estate funds managed by Brookfield ("Brookfield")

May 9, 2022 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 6, 2022 WATERMARK LODGING TRUST, INC. (Exact name of registrant as specified in its charter) Maryland (State or other jurisdiction of incorporation) 000-55461 (Commission File Num

May 9, 2022 EX-99.3

Watermark Lodging Trust to be Acquired by Brookfield Real Estate Funds FREQUENTLY ASKED QUESTIONS

Exhibit 99.3 Watermark Lodging Trust to be Acquired by Brookfield Real Estate Funds FREQUENTLY ASKED QUESTIONS Q: What are the terms of the agreement? A: The details of the agreement between Watermark Lodging Trust (?WLT?) and private real estate funds managed by Brookfield ("Brookfield") are as follows: ? An all-cash transaction for $6.768 per Class A common share and $6.699 per Class T common sh

May 9, 2022 EX-99.3

Frequently asked questions and responses by Watermark Lodging Trust, Inc. for investors and financial advisors.

Exhibit 99.3 Watermark Lodging Trust to be Acquired by Brookfield Real Estate Funds FREQUENTLY ASKED QUESTIONS Q: What are the terms of the agreement? A: The details of the agreement between Watermark Lodging Trust (?WLT?) and private real estate funds managed by Brookfield ("Brookfield") are as follows: ? An all-cash transaction for $6.768 per Class A common share and $6.699 per Class T common sh

May 9, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 6, 2022 WATERMARK LODGING TRU

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 6, 2022 WATERMARK LODGING TRUST, INC. (Exact name of registrant as specified in its charter) Maryland (State or other jurisdiction of incorporation) 000-55461 (Commission File Num

April 27, 2022 10-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A Amendment No. 1

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A Amendment No. 1 ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 WATERMA

March 28, 2022 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☑ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 WATERMARK LODGING TRUST,

March 28, 2022 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 28, 2022 WATERMARK LODGING TRUST, INC. (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5765413 (Commi

March 28, 2022 EX-21.1

Filed herewith

Exhibit 21.1 WATERMARK LODGING TRUST, INC. LIST OF REGISTRANT SUBSIDIARIES Name of Subsidiary Ownership State or Country of Incorporation Arlington 2 Hotel Operator, LLC 100 % Delaware Atlanta Midtown Hotel Operator, Inc. 100 % Delaware Atlanta Peachtree 2 Hotel Mezzanine Operator, LLC 100 % Delaware Atlanta Peachtree 2 Hotel Operator, LLC 100 % Delaware Austin Capitol Hotel Operator, Inc. 80 % De

March 28, 2022 EX-99.1

CONSENT OF CBRE, INC. DBA CBRE HOTELS

Exhibit 99.1 CONSENT OF CBRE, INC. DBA CBRE HOTELS Watermark Lodging Trust, Inc.: We hereby consent to the references to our firm and description of our role in the appraisal of the fair market value of Watermark Lodging Trust’s (the “Company”) real estate portfolio as of December 31, 2021, included in this Current Report on Form 8-K, as amended, and incorporated by reference into the Company’s Re

March 28, 2022 EX-99.2

CONSENT OF ROBERT A. STANGER & CO., INC.

Exhibit 99.2 CONSENT OF ROBERT A. STANGER & CO., INC. Watermark Lodging Trust, Inc.: We hereby consent to the references to our firm and description of our role in the estimates of the fair market value of the Watermark Lodging Trust?s (the ?Company?) mortgage debt encumbering its real estate portfolio as of December 31, 2021 included in this Current Report on Form 8-K, as amended, and incorporate

December 14, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 8, 2021 WATERMARK LODGING TRUST, INC. (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5765413 (Com

November 12, 2021 EX-10.32

Filed herewith

EXHIBIT 10.32 WATERMARK LODGING TRUST, INC. EMPLOYEE RETENTION AND SEVERANCE PLAN This Employee Retention and Severance Plan (the "Plan") is established by Watermark Lodging Trust, Inc., a Maryland real estate investment trust (the "Company"), effective November, 2021. 1.Purpose of the Plan. The Company considers it essential to the operation of the Company that its executives and key employees be

November 12, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2021 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 WATERMARK LODGIN

August 11, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 WATERMARK LODGING TRU

June 17, 2021 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 16, 2021 WATERMARK LODGING TRUST, INC. (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5765413 (Commis

May 25, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 20, 2021 WATERMARK LODGING TRUST, INC. (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5765413 (Commiss

May 12, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2021 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 WATERMARK LODGING TR

April 29, 2021 DEF 14A

- DEF 14A

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ? Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy S

April 6, 2021 S-8

- FORM S-8

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Watermark Lodging Trust, Inc. (Exact name of registrant as specified in its charter) Maryland (State or other jurisdiction of incorporation or organization) 46-5765413 (I.R.S. Employer Identification No.) 150 N. Riverside Plaza, Chicago, Illinois (Address of prin

March 12, 2021 EX-10.31

Filed herewith

EX-10.31 2 wlt202010-kexh1031.htm EX-10.31 Exhibit 10.31 WATERMARK LODGING TRUST, INC. EQUITY INCENTIVE PLAN RESTRICTED STOCK UNIT AWARD AGREEMENT AGREEMENT by and between Watermark Lodging Trust, Inc., a Maryland corporation (the “Company”), and Employee Name (the “Grantee”), dated as of the day of (the “Effective Date”). WHEREAS, the Company maintains the Equity Incentive Plan, as it may be amen

March 12, 2021 EX-21.1

Filed herewith

Exhibit 21.1 WATERMARK LODGING TRUST, INC. LIST OF REGISTRANT SUBSIDIARIES Name of Subsidiary Ownership State or Country of Incorporation Arlington 2 Hotel Operator, LLC 100 % Delaware Atlanta Midtown Hotel Operator, Inc. 100 % Delaware Atlanta Peachtree 2 Hotel Mezzanine Operator, LLC 100 % Delaware Atlanta Peachtree 2 Hotel Operator, LLC 100 % Delaware Austin Capitol Hotel Operator, Inc. 80 % De

March 12, 2021 10-K

Annual Report - 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2020 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 WATERMARK LODGING TRUST,

November 24, 2020 S-8

- FORM S-8

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 ———————————— Watermark Lodging Trust, Inc. (Exact name of registrant as specified in its charter) ———————————— Maryland (State or other jurisdiction of incorporation or organization) 46-5765413 (I.R.S. Employer Identification No.) 150 N. Riverside Plaza, Chicago,

November 19, 2020 EX-99.1

CONSENT OF CBRE, INC. DBA CBRE HOTELS

Exhibit 99.1 CONSENT OF CBRE, INC. DBA CBRE HOTELS Watermark Lodging Trust, Inc.: We hereby consent to the references to our firm and description of our role in the appraisal of the fair market value of Watermark Lodging Trust’s (the “Company”) real estate portfolio as of September 30, 2020, included in this Current Report on Form 8-K, as amended, and incorporated by reference into the Company’s R

November 19, 2020 8-K

Financial Statements and Exhibits, Other Events - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 19, 2020 WATERMARK LODGING TRUST, INC. (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5765413 (Co

November 19, 2020 EX-99.2

CONSENT OF ROBERT A. STANGER & CO., INC.

Exhibit 99.2 CONSENT OF ROBERT A. STANGER & CO., INC. Watermark Lodging Trust, Inc.: We hereby consent to the references to our firm and description of our role in the estimates of the fair market value of the Watermark Lodging Trust’s (the “Company”) mortgage debt encumbering its real estate portfolio as of September 30, 2020 included in this Current Report on Form 8-K, as amended, and incorporat

November 12, 2020 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2020 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 WATERMARK LODGIN

August 24, 2020 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 21, 2020 Watermark Lodging Trust, Inc. (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5765413 (Comm

August 14, 2020 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☑ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2020 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 WATERMARK LODGING TRU

August 3, 2020 EX-99.1

JOINT FILING AGREEMENT

EXHIBIT 1 JOINT FILING AGREEMENT The undersigned hereby agree that they are filing this statement jointly pursuant to Rule 13d-1(k)(1) under the Securities Exchange Act of 1934, as amended (the ?Exchange Act?).

August 3, 2020 EX-99.7

AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT ACP WATERMARK INVESTMENT LLC Dated as of July 21, 2020

Exhibit 7 Execution Version AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT OF ACP WATERMARK INVESTMENT LLC Dated as of July 21, 2020 THE LIMITED LIABILITY COMPANY INTERESTS REPRESENTED BY THIS AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT HAVE BEEN ACQUIRED FOR INVESTMENT AND HAVE NOT BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR UNDER THE DELAWARE SECURITIES ACT, OR OTHER SIMILAR FEDERAL OR STATE STATUTES OR AGENCIES IN RELIANCE UPON EXEMPTIONS FROM REGISTRATION AS PROVIDED IN THOSE STATUTES.

August 3, 2020 SC 13D

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. )* Watermark Lodging Trust, Inc. (Name of Issuer) Class A common stock, par value $0.001 per share Class T c

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. )* Watermark Lodging Trust, Inc. (Name of Issuer) Class A common stock, par value $0.001 per share Class T common stock, par value $0.001 per share (Title of Class of Securities) 94184W 100 94184W 209 (CUSIP Number) Russell Gimelstob & Alex Halpern c/o ACP W

August 3, 2020 EX-99.5

July 21, 2020

EX-5 Exhibit 5 EXECUTION VERSION July 21, 2020 CWA LLC 150 N. Riverside Plaza Suite 4200 Chicago, IL 60606 Attn: Michael G. Medzigian Email: [email protected] Re: Lockup Letter Dear Sirs: Reference is made to that certain Securities Purchase Agreement, dated July 21, 2020 (the “Purchase Agreement”), by and among Watermark Lodging Trust, Inc., a Maryland corporation (the “Company”), CW

July 24, 2020 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Entry into a Material Definitive Agreement, Material Modification to Rights of Security Holders, Unregistered Sales of Equity Securities, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 21, 2020 WATERMARK LODGING TRUST, INC. (Exact name of registrant as specified in its charter) Maryland 000-55461 46-5765413 (State or other jurisdiction of incorporation) (Commis

July 24, 2020 EX-10.2

Incorporated by reference to Exhibit 10.2 to Current Report on Form 8-K, filed on July 24, 2020

Exhibit 10.2 INVESTOR RIGHTS AGREEMENT THIS INVESTOR RIGHTS AGREEMENT (this "Agreement"), dated as of July 24, 2020, is by and among WATERMARK LODGING TRUST, INC., a Maryland corporation (the "Company"), CWI 2 OP, LP, a Delaware limited partnership (the "Operating Partnership") and ACP WATERMARK INVESTMENT LLC, a Delaware limited liability company (the “Purchaser”). The Purchaser and any other Per

July 24, 2020 EX-3.1

Incorporated by reference to Exhibit 3.1 to Current Report on Form 8-K, filed on July 24, 2020

Exhibit 3.1 WATERMARK LODGING TRUST, INC. ARTICLES SUPPLEMENTARY SERIES B CUMULATIVE REDEEMABLE PREFERRED STOCK WATERMARK LODGING TRUST, INC., a Maryland corporation (the “Corporation”), hereby certifies to the State Department of Assessments and Taxation of Maryland that: FIRST: Pursuant to the authority expressly vested in the Board of Directors of the Corporation (the “Board of Directors”) by A

July 24, 2020 EX-4.1

Incorporated by reference to Exhibit 4.1 to Current Report on Form 8-K, filed on July 24, 2020

Exhibit 4.1 THIS WARRANT AND THE SECURITIES ISSUABLE UPON THE EXERCISE HEREOF HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR QUALIFIED UNDER ANY STATE SECURITIES LAWS. SUCH SECURITIES MAY NOT BE SOLD, OFFERED FOR SALE, PLEDGED, HYPOTHECATED OR OTHERWISE TRANSFERRED EXCEPT PURSUANT TO AN EFFECTIVE REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR AN

July 24, 2020 EX-99.1

Watermark Lodging Trust, Inc. Completes Strategic Financing Transaction Transaction Provides Significant Operational and Financial Flexibility

Exhibit 99.1 Watermark Lodging Trust, Inc. Completes Strategic Financing Transaction Transaction Provides Significant Operational and Financial Flexibility CHICAGO – July 24, 2020 – Watermark Lodging Trust, Inc. (“Watermark” or the “Company”) announced today that the Company has completed a strategic financing transaction with a joint venture between affiliates of Ascendant Capital Partners (“Asce

July 24, 2020 EX-10.1

Incorporated by reference to Exhibit 10.1 to Current Report on Form 8-K, filed on July 24, 2020

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This Securities Purchase Agreement (this “Agreement”) is dated as of July 21, 2020 among Watermark Lodging Trust, Inc., a Maryland corporation (the “Company”), CWI 2 OP, LP, a Delaware limited partnership (the “Operating Partnership”), ACP Watermark Investment LLC, a Delaware limited liability company (the “Purchaser”), and Ascendant Capital Fund LP, a De

July 6, 2020 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Other Events, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 30, 2020 Watermark Lodging Trust, Inc. (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5765413 (Commis

June 26, 2020 EX-99.3

WATERMARK LODGING TRUST, INC. UNAUDITED PRO FORMA CONSOLIDATED FINANCIAL INFORMATION

EXHIBIT 99.3 WATERMARK LODGING TRUST, INC. UNAUDITED PRO FORMA CONSOLIDATED FINANCIAL INFORMATION This unaudited pro forma consolidated financial information should be read in conjunction with the unaudited financial statements of Carey Watermark Investors Incorporated ("CWI 1") and Watermark Lodging Trust, Inc. (“WLT”), formerly Carey Watermark Investors 2 Incorporated (“CWI 2”) as of and for the

June 26, 2020 EX-99.1

Page No.

EXHIBIT 99.1 INDEX Page No. FINANCIAL INFORMATION Financial Statements (Unaudited) Consolidated Balance Sheets as of March 31, 2020 and December 31, 2019 2 Consolidated Statements of Operations for the Three Months Ended March 31, 2020 and 2019 3 Consolidated Statements of Comprehensive Loss for the Three Months Ended March 31, 2020 and 2019 4 Consolidated Statements of Equity for the Three Months

June 26, 2020 EX-99.2

Page No.

EXHIBIT 99.2 INDEX Page No. FINANCIAL INFORMATION Financial Statements Report of Independent Registered Public Accounting Firm 2 Consolidated Balance Sheets as of December 31, 2019 and 2018 3 Consolidated Statements of Operations for the Years Ended December 31, 2019, 2018 and 2017 4 Consolidated Statements of Comprehensive (Loss) Income for the Years Ended December 31, 2019, 2018 and 2017 5 Conso

June 26, 2020 8-K/A

Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 9, 2020 WATERMARK LODGING TRUST, INC. (Exact name of registrant as specified in its charter) 000-55461 46-5765413 (Commission File Number) (IRS Employer Identification No.) 15

June 26, 2020 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2020 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 WATERMARK LODGING TR

June 26, 2020 DEFA14A

- DEFA14A

DEFA14A 1 tm2023531d1defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 2) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only

June 16, 2020 DEFA14A

- DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ¨ Defin

May 14, 2020 8-K

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 14, 2020 WATERMARK LODGING TRUST, INC. (Exact Name of Registrant as Specified in Charter) 000-55461 46-5765413 (Commission File Number) (IRS Employer Identification No.) 150 N. Ri

May 6, 2020 DEF 14A

- DEF 14A

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant þ Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy S

May 1, 2020 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 29, 2020 WATERMARK LODGING TRUST, INC. (Exact Name of Registrant as Specified in Charter) 000-55461 46-5765413 (Commission File Number) (I.R.S. Employer Identification No.) 150

April 29, 2020 8-K

Other Events

8-K 1 tm2018074d18k.htm FORM 8-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 29, 2020 WATERMARK LODGING TRUST, INC. (Exact Name of Registrant as Specified in Charter) 000-55461 46-5765413 (Commission File Number) (I.R.S.

April 13, 2020 SC 13G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No._)*

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No.)* Carey Watermark Investors 2 Incorporated (Name of Issuer) Common Stock - Class A, par value $0.001 per share Common Stock - Class T, par value $0.001 per share (Title of Class of Securities) 14179D107 14179D206 (CUSIP Number) April 13, 2020 (Date of Event

April 13, 2020 EX-99.1

Joint Filing Agreement

EXHIBIT 99.1 Joint Filing Agreement In accordance with Rule 13d-1(k) under the Securities Exchange Act of 1934, as amended, the persons named below agree to the joint filing of a statement on Schedule 13G (including amendments thereto) with respect to the shares of Common Stock - Class A, par value $0.001 per share, and Common Stock - Class T, par value $0.001 per share, of Carey Watermark Investo

April 13, 2020 EX-2.1

Incorporated by reference to Exhibit 2.1 to Current Report on Form 8-K, filed on April 13, 2020

Exhibit 2.1 STRICTLY CONFIDENTIAL April 13, 2020 Carey Watermark Investors 2 Incorporated 50 Rockefeller Plaza New York, NY 10020 Attn: Chairman of the Board of Directors; General Counsel Re: Temporary Modification to Compensation Reference is made to that certain Agreement, executed on October 22, 2019 (the ?Employment Agreement?), by and between Carey Watermark Investors 2 Incorporated (and any

April 13, 2020 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Entry into a Material Definitive Agreement, Termination of a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits, Completion of Acquisition or Disposition of Assets

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 9, 2020 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5765

April 13, 2020 EX-3.1

Incorporated by reference to Exhibit 3.1 to Current Report on Form 8-K, filed on April 13, 2020

Exhibit 3.1 EXECUTION VERSION CAREY WATERMARK INVESTORS 2 INCORPORATED ARTICLES OF AMENDMENT CAREY WATERMARK INVESTORS 2 INCORPORATED, a Maryland corporation (the “Corporation”), desires to amend its charter as currently in effect and as hereinafter amended. FIRST: The charter of the Corporation as currently in effect (the “Charter”) is hereby amended by deleting clause (A) of Section 9.3(f). SECO

April 13, 2020 EX-3.2

Incorporated by reference to Exhibit 3.2 to Current Report on Form 8-K, filed on April 13, 2020

Exhibit 3.2 EXECUTION VERSION WATERMARK LODGING TRUST INCORPORATED ARTICLES OF AMENDMENT THIS IS TO CERTIFY THAT: FIRST: The charter of Watermark Lodging Trust Incorporated, a Maryland corporation (the “Corporation”), is hereby amended by deleting the existing Article I in its entirety and substituting in lieu thereof a new article to read as follows: ARTICLE I NAME The name of the corporation (wh

April 10, 2020 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Submission of Matters to a Vote of Security Holders

8-K 1 tm2015455-18k.htm FORM 8-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 8, 2020 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of

April 10, 2020 EX-99.1

Carey Watermark Investors 1 and Carey Watermark Investors 2 Stockholders Approve Merger

Exhibit 99.1 Carey Watermark Investors 1 and Carey Watermark Investors 2 Stockholders Approve Merger NEW YORK, April 9, 2020 – Carey Watermark Investors 1 Incorporated (CWI® 1) and Carey Watermark Investors 2 Incorporated (CWI® 2) announced today that the stockholders of each company approved the proposed merger of the two companies to create Watermark Lodging Trust (WLT), a self-managed non-trade

March 31, 2020 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 27, 2020 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-576

March 31, 2020 425

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 27, 2020 Carey Watermark In

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 27, 2020 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-576

March 31, 2020 EX-2.1

Incorporated by reference to Exhibit 2.1 to Current Report on Form 8-K, filed on March 31, 2020

Exhibit 2.1 March 27, 2020 STRICTLY CONFIDENTIAL Carey Watermark Investors 2 Incorporated 50 Rockefeller Plaza New York, NY 10020 Attn: The Special Committee of the Board of Directors; Chief Legal Officer Email: [email protected] Re: Suspension of Dividends; Outside Date Dear Robert: Reference is made to (x) the Agreement and Plan of Merger, dated as of October 22, 2019 (the “Merger Agreem

March 31, 2020 EX-2.1

Letter agreement, dated March 27, 2020, by and among Carey Watermark Investors Incorporated, Carey Watermark Investors 2 Incorporated, and Apex Merger Sub LLC.

Exhibit 2.1 March 27, 2020 STRICTLY CONFIDENTIAL Carey Watermark Investors 2 Incorporated 50 Rockefeller Plaza New York, NY 10020 Attn: The Special Committee of the Board of Directors; Chief Legal Officer Email: [email protected] Re: Suspension of Dividends; Outside Date Dear Robert: Reference is made to (x) the Agreement and Plan of Merger, dated as of October 22, 2019 (the ?Merger Agreem

March 24, 2020 425

Carey Watermark Investors Incorporated and Carey Watermark Investors 2 Incorporated 50 Rockefeller Center New York, NY 10020 ADDITIONAL INFORMATION REGARDING THE SPECIAL MEETINGS OF STOCKHOLDERS PREVIOUSLY SCHEDULED TO BE HELD ON THURSDAY, MARCH 26,

425 1 a20-133264425.htm 425 Filed pursuant to Rule 425 under the Securities Exchange Act of 1933, as amended, and deemed filed pursuant to Rule 14a-6 (b) of the Securities Exchange Act of 1934, as amended. Filing Person: Carey Watermark Investors 2 Incorporated Subject Company: Carey Watermark Investors Incorporated Form S-4 File No.: 333-235428 Carey Watermark Investors Incorporated and Carey Wat

March 19, 2020 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 19, 2020 Carey Watermark In

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 19, 2020 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-576

March 19, 2020 425

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 19, 2020 Carey Watermark In

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 19, 2020 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-576

March 18, 2020 425

Dear Fellow Stockholder,

Filed pursuant to Rule 425 under the Securities Exchange Act of 1933, as amended, and deemed filed pursuant to Rule 14a-6 (b) of the Securities Exchange Act of 1934, as amended.

March 18, 2020 425

NEW YORK, March 18, 2020 — Carey Watermark Investors 1 Incorporated (CWI

Filed pursuant to Rule 425 under the Securities Exchange Act of 1933, as amended, and deemed filed pursuant to Rule 14a-6 (b) of the Securities Exchange Act of 1934, as amended.

March 18, 2020 425

CAREY WATERMARK INVESTORS INCORPORATED CAREY WATERMARK INVESTORS 2 INCORPORATED Supplement To Proxy Statement

Filed pursuant to Rule 425 under the Securities Exchange Act of 1933, as amended, and deemed filed pursuant to Rule 14a-6 (b) of the Securities Exchange Act of 1934, as amended.

March 12, 2020 EX-4.3

Filed herewith

Exhibit 4.3 DESCRIPTION OF THE REGISTRANT?S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 As of December 31, 2019, Carey Watermark Investors 2 Incorporated has its common stock, $0.001 par value per share, registered under Section 12 of the Securities Exchange Act of 1934, as amended (the ?Exchange Act?). References in the following discussion to ?CWI 2,? ?we,

March 12, 2020 10-K

The registrant's Annual Report on Form 10-K for the fiscal year ended December 31, 2019, filed on March 12, 2020.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K þ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2019 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 CAREY WATERMARK INVESTORS

March 12, 2020 EX-10.16

Filed herewith

Exhibit 10.16 SECOND AMENDMENT TO LOAN AGREEMENT THIS SECOND AMENDMENT TO LOAN AGREEMENT (this ?Amendment?) is dated November 8, 2019 and effective as of September 26, 2019 (the ?Effective Date?), by and between CWI 2 OP LP, a Delaware limited partnership (?Borrower?), and WPC HOLDCO LLC, a Maryland limited liability company (?Lender?). RECITALS A.Borrower is the maker of that certain Amended, Res

March 12, 2020 EX-21.1

Filed herewith

Exhibit 21.1 CAREY WATERMARK INVESTORS 2 INCORPORATED LIST OF REGISTRANT SUBSIDIARIES Name of Subsidiary Ownership State or Country of Incorporation Arlington 2 Hotel Operator, LLC 100 % Delaware Atlanta Peachtree 2 Hotel Mezzanine Operator, LLC 100 % Delaware Atlanta Peachtree 2 Hotel Operator, LLC 100 % Delaware Bellevue 2 Hotel Operator, Inc. 95 % Delaware Charlotte 2 Hotel Operator, LLC 100 %

March 12, 2020 EX-10.17

Filed herewith

Exhibit 10.17 THIRD AMENDMENT TO LOAN AGREEMENT THIS THIRD AMENDMENT TO LOAN AGREEMENT (this “Amendment”) is dated March 6, 2020 and effective as of January 16, 2020 (the “Effective Date”), by and between CWI 2 OP LP, a Delaware limited partnership (“Borrower”), and WPC HOLDCO LLC, a Maryland limited liability company (“Lender”). RECITALS A.Borrower is the maker of that certain Amended, Restated a

March 12, 2020 EX-99.1

Filed herewith

Exhibit 99.1 Ritz-Carlton Bacara, Santa Barbara Hotel Combined Financial Report Years Ended December 31, 2019 and 2018 and Period from September 28, 2017 (Acquisition) through December 31, 2017 (Unaudited) Includes accounts of: CWI Santa Barbara Hotel, LP CWI 2 Santa Barbara Hotel, LP CWI Santa Barbara Mezz, LP CWI 2 Santa Barbara Mezz, LP CWI Santa Barbara Hotel GP, LLC CWI 2 Santa Barbara Hotel

January 14, 2020 424B3

YOUR VOTE IS VERY IMPORTANT

Use these links to rapidly review the document TABLE OF CONTENTS INDEX TO FINANCIAL INFORMATION TABLE OF CONTENTS Table of Contents Filed Pursuant to Rule 424(b)(3) Registration No.

January 14, 2020 425

January 2020

Filed pursuant to Rule 425 under the Securities Exchange Act of 1933, as amended, and deemed filed pursuant to Rule 14a-6 (b) of the Securities Exchange Act of 1934, as amended.

January 14, 2020 425

Filed pursuant to Rule 425 under the Securities Act of 1933, as amended and deemed filed pursuant to Rule 14a-6 (b) of the Securities Exchange Act of 1934, as amended. Filing Person: Carey Watermark Investors 2 Incorporated Subject Company: Carey Wat

Filed pursuant to Rule 425 under the Securities Act of 1933, as amended and deemed filed pursuant to Rule 14a-6 (b) of the Securities Exchange Act of 1934, as amended.

January 10, 2020 EX-99.8

Consent of John J. Park to become a director

Exhibit 99.8 CONSENT OF PERSON TO BE NAMED AS A DIRECTOR As required by Rule 438 under the Securities Act of 1933, as amended, the undersigned hereby consents to being named in the Registration Statement on Form S-4 (together with any amendments or supplements, the “Registration Statement”), filed by Carey Watermark Investors Incorporated and Carey Watermark Investors 2 Incorporated (“CWI 2”) with

January 10, 2020 EX-99.7

Consent of Michael D. Johnson to become a director

Exhibit 99.7 CONSENT OF PERSON TO BE NAMED AS A DIRECTOR As required by Rule 438 under the Securities Act of 1933, as amended, the undersigned hereby consents to being named in the Registration Statement on Form S-4 (together with any amendments or supplements, the “Registration Statement”), filed by Carey Watermark Investors Incorporated and Carey Watermark Investors 2 Incorporated (“CWI 2”) with

January 10, 2020 S-4/A

As filed with the Securities and Exchange Commission on January 10, 2020

Use these links to rapidly review the document TABLE OF CONTENTS INDEX TO FINANCIAL INFORMATION TABLE OF CONTENTS Table of Contents As filed with the Securities and Exchange Commission on January 10, 2020 Registration No.

January 10, 2020 EX-99.9

Consent of Simon M. Turner to become a director

Exhibit 99.9 CONSENT OF PERSON TO BE NAMED AS A DIRECTOR As required by Rule 438 under the Securities Act of 1933, as amended, the undersigned hereby consents to being named in the Registration Statement on Form S-4 (together with any amendments or supplements, the “Registration Statement”), filed by Carey Watermark Investors Incorporated and Carey Watermark Investors 2 Incorporated (“CWI 2”) with

January 10, 2020 EX-99.2

Form of Proxy Card—Carey Watermark Investors 2 Incorporated

Exhibit 99.2 SCAN TO VIEW MATERIALS & VOTE CAREY WATERMARK INVESTORS 2 INCORPORATED ATTN: INVESTOR RELATIONS 50 ROCKEFELLER PLAZA NEW YORK, NY 10020 VOTE BY INTERNET - www.proxyvote.com or scan the QR Barcode above Use the Internet to transmit your voting instructions and for electronic delivery of information up until 11:59 P.M. Eastern Time the day before the meeting date. Follow the instruction

January 10, 2020 EX-8.3

Opinion of Hogan Lovells US LLP regarding tax matters

Exhibit 8.3 Hogan Lovells US LLP Columbia Square 555 Thirteenth Street, NW Washington, DC 20004 T +1 202 637 5600 F +1 202 637 5910 www.hoganlovells.com January 10, 2020 Board of Directors Carey Watermark Investors Incorporated 50 Rockefeller Plaza New York, New York 10020 Ladies and Gentlemen: We have acted as special tax counsel to Carey Watermark Investors Incorporated, a Maryland corporation (

January 10, 2020 EX-99.6

Consent of Charles S. Henry to become a director

Exhibit 99.6 CONSENT OF PERSON TO BE NAMED AS A DIRECTOR As required by Rule 438 under the Securities Act of 1933, as amended, the undersigned hereby consents to being named in the Registration Statement on Form S-4 (together with any amendments or supplements, the “Registration Statement”), filed by Carey Watermark Investors Incorporated and Carey Watermark Investors 2 Incorporated (“CWI 2”) with

January 10, 2020 EX-99.1

Form of Proxy Card—Carey Watermark Investors Incorporated

Exhibit 99.1 SCAN TO VIEW MATERIALS & VOTE CAREY WATERMARK INVESTORS INCORPORATED ATTN: INVESTOR RELATIONS 50 ROCKEFELLER PLAZA NEW YORK, NY 10020 VOTE BY INTERNET - www.proxyvote.com or scan the QR Barcode above Use the Internet to transmit your voting instructions and for electronic delivery of information up until 11:59 P.M. Eastern Time the day before the meeting date. Follow the instructions

December 9, 2019 EX-99.3

Consent of Barclays Capital Inc.

Exhibit 99.3 745 Seventh Avenue New York, NY 10019 United States December 9, 2019 CONSENT OF BARCLAYS CAPITAL INC. We hereby consent to (i) the inclusion of our opinion letter, dated October 21, 2019, to the Special Committee of the Board of Directors of Carey Watermark Investors Incorporated, as Annex E to the Joint Proxy Statement/Prospectus that forms a part of the Registration Statement on For

December 9, 2019 EX-99.5

Consent of Duff & Phelps, LLC

Exhibit 99.5 December 9, 2019 CONSENT OF DUFF & PHELPS, LLC We hereby consent to the inclusion of our opinion letter, dated October 22, 2019, to the Special Committee of the Board of Directors of Carey Watermark Investors 2 Incorporated (“CWI 2”) as Annex G to the Joint Proxy Statement/Prospectus, which forms a part of the Registration Statement on Form S-4 of CWI 2 (the “Registration Statement”),

December 9, 2019 EX-99.4

Consent of Morgan Stanley & Co. LLC

Exhibit 99.4 Consent of Morgan Stanley & Co. LLC We hereby consent to the use in the Registration Statement of Carey Watermark Investors 2 Incorporated on Form S-4 and in the Joint Proxy Statement/Prospectus of Carey Watermark Investors 2 Incorporated and Carey Watermark Investors Incorporated, which is part of the Registration Statement, of our written opinion, dated October 21, 2019 appearing as

December 9, 2019 S-4

Powers of Attorney

Use these links to rapidly review the document TABLE OF CONTENTS INDEX TO FINANCIAL INFORMATION TABLE OF CONTENTS Table of Contents As filed with the Securities and Exchange Commission on December 9, 2019 Registration No.

November 8, 2019 CORRESP

Mallika Sinha Chief Financial Officer TEL +1-212-492-8958 FAX +1-212-492-8922 [email protected]

Mallika Sinha Chief Financial Officer TEL +1-212-492-8958 FAX +1-212-492-8922 msinha@wpcarey.

November 8, 2019 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q þ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2019 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 CAREY WATERMARK

October 28, 2019 EX-99.1

If you have trouble viewing this email, read the online version.

Exhibit 99.1 If you have trouble viewing this email, read the online version. CWI® 1 and CWI® 2 Proposed Merger Webinar: Now Available On-Demand We are pleased to provide you with a replay of our recent webinar discussing the proposed merger of Carey Watermark Investors 1 and Carey Watermark Investors 2. Listen to the replay to hear management discuss how the proposed transaction: · Combines CWI 1

October 28, 2019 425

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 28, 2019 Carey Watermark

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 28, 2019 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5

October 28, 2019 EX-99.1

If you have trouble viewing this email, read the online version.

Exhibit 99.1 If you have trouble viewing this email, read the online version. CWI® 1 and CWI® 2 Proposed Merger Webinar: Now Available On-Demand We are pleased to provide you with a replay of our recent webinar discussing the proposed merger of Carey Watermark Investors 1 and Carey Watermark Investors 2. Listen to the replay to hear management discuss how the proposed transaction: · Combines CWI 1

October 28, 2019 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 28, 2019 Carey Watermark

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 28, 2019 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5

October 24, 2019 425

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 24, 2019 Carey Watermark

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 24, 2019 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5

October 24, 2019 EX-99.1

CWI Presentation Script

Exhibit 99.1 CWI Presentation Script Opening: Becky: Good afternoon everyone and thank you for joining us today! With me to discuss the proposed merger of CWI 1 and CWI 2 are Michael Medzigian and Mallika Sinha, CEO and CFO, of CWI 1 and CWI 2. Following the presentation, Michael and Mallika?along with John Park, President of W. P. Carey, will be available to answer your questions about the transa

October 24, 2019 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 24, 2019 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5

October 24, 2019 EX-99.1

CWI Presentation Script

Exhibit 99.1 CWI Presentation Script Opening: Becky: Good afternoon everyone and thank you for joining us today! With me to discuss the proposed merger of CWI 1 and CWI 2 are Michael Medzigian and Mallika Sinha, CEO and CFO, of CWI 1 and CWI 2. Following the presentation, Michael and Mallika…along with John Park, President of W. P. Carey, will be available to answer your questions about the transa

October 22, 2019 8-K

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Entry into a Material Definitive Agreement, Termination of a Material Definitive Agreement, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 22, 2019 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5

October 22, 2019 EX-2.2

Incorporated by reference to Exhibit 2.2 to Current Report on Form 8-K, filed on October 22, 2019

Exhibit 2.2 INTERNALIZATION AGREEMENT THIS INTERNALIZATION AGREEMENT, dated as of October 22, 2019 (this “Agreement”), is entered into by and among Carey Watermark Investors Incorporated, a Maryland corporation (“CWI 1”), CWI OP, LP, a Delaware limited partnership and the operating partnership of CWI 1 (“CWI 1 OP,” and together with CWI 1, the “CWI 1 Entities”), Carey Watermark Investors 2 Incorpo

October 22, 2019 EX-99.1

Carey Watermark Investors 1 and Carey Watermark Investors 2 Announce Proposed Merger 100% stock-for-stock merger and management internalization to form Watermark Lodging Trust, a $4.6 billion lodging REIT, increasing scale and operational efficiencie

Exhibit 99.1 Carey Watermark Investors 1 and Carey Watermark Investors 2 Announce Proposed Merger 100% stock-for-stock merger and management internalization to form Watermark Lodging Trust, a $4.6 billion lodging REIT, increasing scale and operational efficiencies for long-term value creation NEW YORK, October 22, 2019 – Carey Watermark Investors 1 Incorporated (CWI® 1) and Carey Watermark Investo

October 22, 2019 EX-2.1

Agreement and Plan of Merger, dated as of October 22, 2019, among Carey Watermark Investors Incorporated, Carey Watermark Investors 2 Incorporated, and Apex Merger Sub LLC.*

Exhibit 2.1 AGREEMENT AND PLAN OF MERGER BY AND AMONG CAREY WATERMARK INVESTORS 2 INCORPORATED, APEX MERGER SUB LLC, AND CAREY WATERMARK INVESTORS INCORPORATED DATED AS OF OCTOBER 22, 2019 TABLE OF CONTENTS Page ARTICLE 1 DEFINITIONS 2 Section 1.1 Definitions 2 Section 1.2 Interpretation and Rules of Construction 14 ARTICLE 2 THE REIT MERGER 15 Section 2.1 The REIT Merger; Other Transactions 15 Se

October 22, 2019 EX-10.3

Transition Services Agreement, dated as of October 22, 2019, between W. P. Carey Inc., and Carey Watermark Investors 2 Incorporated.

Exhibit 10.3 TRANSITION SERVICES AGREEMENT THIS TRANSITION SERVICES AGREEMENT (this ?Agreement?), is made and entered into as of October 22, 2019, by and between W. P. Carey Inc., a Maryland corporation (?WPC?), and Carey Watermark Investors 2 Incorporated, a Maryland corporation (?Recipient?). For purposes of this Agreement, WPC is sometimes referred to as a ?Service Provider.? Service Provider a

October 22, 2019 EX-99.2

Dear Stockholder,

Exhibit 99.2 October 2019 Dear Stockholder, On October 22, 2019, CWI 1 and CWI 2 announced that the two companies have entered into a definitive merger agreement under which the two companies will merge in an all-stock transaction to create Watermark Lodging Trust (WLT), a $4.6 billion, internally-managed real estate investment trust (REIT) with increased scale and operating efficiencies, position

October 22, 2019 EX-99.2

Dear Stockholder,

Exhibit 99.2 October 2019 Dear Stockholder, On October 22, 2019, CWI 1 and CWI 2 announced that the two companies have entered into a definitive merger agreement under which the two companies will merge in an all-stock transaction to create Watermark Lodging Trust (WLT), a $4.6 billion, internally-managed real estate investment trust (REIT) with increased scale and operating efficiencies, position

October 22, 2019 EX-99.3

The Proposed Merger and Internalization of CWI 1 and CWI 2 October 2019

Exhibit 99.3 The Proposed Merger and Internalization of CWI 1 and CWI 2 October 2019 Transaction Objectives ? Combine Carey Watermark Investors (?CWI 1?) and Carey Watermark Investors 2 (?CWI 2?) to create Watermark Lodging Trust (?WLT?), a company with $4.6 billion(1) of high-quality lodging assets in attractive markets with significant barriers to entry and favorable growth prospects ? Improve o

October 22, 2019 EX-99.1

Carey Watermark Investors 1 and Carey Watermark Investors 2 Announce Proposed Merger 100% stock-for-stock merger and management internalization to form Watermark Lodging Trust, a $4.6 billion lodging REIT, increasing scale and operational efficiencie

Exhibit 99.1 Carey Watermark Investors 1 and Carey Watermark Investors 2 Announce Proposed Merger 100% stock-for-stock merger and management internalization to form Watermark Lodging Trust, a $4.6 billion lodging REIT, increasing scale and operational efficiencies for long-term value creation NEW YORK, October 22, 2019 – Carey Watermark Investors 1 Incorporated (CWI® 1) and Carey Watermark Investo

October 22, 2019 425

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 22, 2019 Carey Watermark

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 22, 2019 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5

October 22, 2019 EX-10.1

Incorporated by reference to Exhibit 10.1 to Current Report on Form 8-K, filed on October 22, 2019

Exhibit 10.1 COMMITMENT AGREEMENT THIS COMMITMENT AGREEMENT (this ?Agreement?) is made and entered into as of October 1, 2019 (?Effective Date?), by and between Watermark Capital Partners, LLC, a Delaware limited liability company (?Watermark?), Carey Watermark Investors Incorporated, a Maryland corporation (?CWI 1?), Carey Watermark Investor 2 Incorporated, a Maryland corporation (?CWI 2,? and to

October 22, 2019 EX-10.2

Transition Services Agreement, dated as of October 22, 2019, between Watermark Capital Partners, LLC, and Carey Watermark Investors 2 Incorporated.

Exhibit 10.2 TRANSITION SERVICES AGREEMENT THIS TRANSITION SERVICES AGREEMENT (this “Agreement”), is made and entered into as of October 22, 2019, by and between Watermark Capital Partners, LLC, a Delaware limited liability company (“Watermark”), and Carey Watermark Investors 2 Incorporated, a Maryland corporation (“CWI 2”), and shall become automatically effective on the Effective Date as defined

October 22, 2019 EX-2.1

Incorporated by reference to Exhibit 2.1 to Current Report on Form 8-K, filed on October 22, 2019

Exhibit 2.1 AGREEMENT AND PLAN OF MERGER BY AND AMONG CAREY WATERMARK INVESTORS 2 INCORPORATED, APEX MERGER SUB LLC, AND CAREY WATERMARK INVESTORS INCORPORATED DATED AS OF OCTOBER 22, 2019 TABLE OF CONTENTS Page ARTICLE 1 DEFINITIONS 2 Section 1.1 Definitions 2 Section 1.2 Interpretation and Rules of Construction 14 ARTICLE 2 THE REIT MERGER 15 Section 2.1 The REIT Merger; Other Transactions 15 Se

October 22, 2019 EX-10.4

Incorporated by reference to Exhibit 10.4 to Current Report on Form 8-K, filed on October 22, 2019

Exhibit 10.4 EXECUTION COPY EMPLOYMENT AGREEMENT AGREEMENT (the ?Agreement?) by and among Carey Watermark Investors 2 Incorporated and any successor in interest thereto (the ?Employer?), and Michael G. Medzigian (the ?Executive?), executed on October 22, 2019 (the ?Effective Date?). WHEREAS, Carey Watermark Investors Incorporated, Carey Watermark Investors 2 Incorporated and Apex Merger Sub LLC ha

October 22, 2019 EX-2.2

Internalization Agreement, dated as of October 22, 2019, among Carey Watermark Investors Incorporated, CWI OP, LP, Carey Watermark Investors 2 Incorporated, CWI 2 OP, LP, W. P. Carey Inc., Carey Watermark Holdings, LLC, CLA Holdings, LLC, Carey REIT II, Inc., WPC Holdco LLC, Carey Watermark Holdings 2, LLC, Carey Lodging Advisors, LLC, Watermark Capital Partners, LLC, CWA, LLC, and CWA 2, LLC.

Exhibit 2.2 INTERNALIZATION AGREEMENT THIS INTERNALIZATION AGREEMENT, dated as of October 22, 2019 (this “Agreement”), is entered into by and among Carey Watermark Investors Incorporated, a Maryland corporation (“CWI 1”), CWI OP, LP, a Delaware limited partnership and the operating partnership of CWI 1 (“CWI 1 OP,” and together with CWI 1, the “CWI 1 Entities”), Carey Watermark Investors 2 Incorpo

October 22, 2019 EX-10.4

Employment Agreement, dated as of October 22, 2019, between Carey Watermark Investors 2 Incorporated and Michael G. Medzigian.

Exhibit 10.4 EXECUTION COPY EMPLOYMENT AGREEMENT AGREEMENT (the “Agreement”) by and among Carey Watermark Investors 2 Incorporated and any successor in interest thereto (the “Employer”), and Michael G. Medzigian (the “Executive”), executed on October 22, 2019 (the “Effective Date”). WHEREAS, Carey Watermark Investors Incorporated, Carey Watermark Investors 2 Incorporated and Apex Merger Sub LLC ha

October 22, 2019 EX-10.2

Incorporated by reference to Exhibit 10.2 to Current Report on Form 8-K, filed on October 22, 2019

Exhibit 10.2 TRANSITION SERVICES AGREEMENT THIS TRANSITION SERVICES AGREEMENT (this “Agreement”), is made and entered into as of October 22, 2019, by and between Watermark Capital Partners, LLC, a Delaware limited liability company (“Watermark”), and Carey Watermark Investors 2 Incorporated, a Maryland corporation (“CWI 2”), and shall become automatically effective on the Effective Date as defined

October 22, 2019 EX-10.3

Incorporated by reference to Exhibit 10.3 to Current Report on Form 8-K, filed on October 22, 2019

Exhibit 10.3 TRANSITION SERVICES AGREEMENT THIS TRANSITION SERVICES AGREEMENT (this “Agreement”), is made and entered into as of October 22, 2019, by and between W. P. Carey Inc., a Maryland corporation (“WPC”), and Carey Watermark Investors 2 Incorporated, a Maryland corporation (“Recipient”). For purposes of this Agreement, WPC is sometimes referred to as a “Service Provider.” Service Provider a

October 22, 2019 EX-99.3

The Proposed Merger and Internalization of CWI 1 and CWI 2 October 2019

Exhibit 99.3 The Proposed Merger and Internalization of CWI 1 and CWI 2 October 2019 Transaction Objectives ? Combine Carey Watermark Investors (?CWI 1?) and Carey Watermark Investors 2 (?CWI 2?) to create Watermark Lodging Trust (?WLT?), a company with $4.6 billion(1) of high-quality lodging assets in attractive markets with significant barriers to entry and favorable growth prospects ? Improve o

October 22, 2019 EX-10.1

Commitment Agreement, dated as of October 1, 2019, among Watermark Capital Partners, LLC, Carey Watermark Investors Incorporated, Carey Watermark Investors 2 Incorporated, and Michael Medzigian.

Exhibit 10.1 COMMITMENT AGREEMENT THIS COMMITMENT AGREEMENT (this “Agreement”) is made and entered into as of October 1, 2019 (“Effective Date”), by and between Watermark Capital Partners, LLC, a Delaware limited liability company (“Watermark”), Carey Watermark Investors Incorporated, a Maryland corporation (“CWI 1”), Carey Watermark Investor 2 Incorporated, a Maryland corporation (“CWI 2,” and to

August 13, 2019 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q þ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2019 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 CAREY WATERMARK INVES

June 25, 2019 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 25, 2019 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5765

May 10, 2019 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q þ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2019 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 CAREY WATERMARK INVE

April 22, 2019 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Ame

Use these links to rapidly review the document Table of Contents Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

April 10, 2019 EX-99.2

CONSENT OF ROBERT A. STANGER & CO., INC.

Exhibit 99.2 CONSENT OF ROBERT A. STANGER & CO., INC. Carey Watermark Investors 2 Incorporated: We hereby consent to the references to our firm and description of our role in the estimates of the fair market value of the Carey Watermark Investors 2 Incorporated’s (the “Company”) mortgage debt encumbering its real estate portfolio as of December 31, 2018, included in this Current Report on Form 8-K

April 10, 2019 EX-99.1

CONSENT OF CBRE, INC. DBA CBRE HOTELS

Exhibit 99.1 CONSENT OF CBRE, INC. DBA CBRE HOTELS Carey Watermark Investors 2 Incorporated: We hereby consent to the references to our firm and description of our role in the appraisal of the fair market value of Carey Watermark Investors 2 Incorporated’s (the “Company”) real estate portfolio as of December 31, 2018, included in this Current Report on Form 8-K, as amended, and incorporated by ref

April 10, 2019 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 10, 2019 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-576

March 15, 2019 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2018 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 CAREY WATERMARK INVESTORS

March 15, 2019 EX-99.1

Filed herewith

Exhibit 99.1 Ritz-Carlton Bacara, Santa Barbara Hotel Combined Financial Report Year Ended December 31, 2018 and Period from September 28, 2017 (Acquisition) through December 31, 2017 (Unaudited) Includes accounts of: CWI Santa Barbara Hotel, LP CWI 2 Santa Barbara Hotel, LP CWI Santa Barbara Mezz, LP CWI 2 Santa Barbara Mezz, LP CWI Santa Barbara Hotel GP, LLC CWI 2 Santa Barbara Hotel GP, LLC Sa

March 15, 2019 EX-21.1

Subsidiaries of Carey Watermark Investors 2 Incorporated

Exhibit 21.1 CAREY WATERMARK INVESTORS 2 INCORPORATED LIST OF REGISTRANT SUBSIDIARIES Name of Subsidiary Ownership State or Country of Incorporation Arlington 2 Hotel Operator, LLC 100 % Delaware Atlanta Peachtree 2 Hotel Mezzanine Operator, LLC 100 % Delaware Atlanta Peachtree 2 Hotel Operator, LLC 100 % Delaware Bellevue 2 Hotel Operator, Inc. 95 % Delaware Charlotte 2 Hotel Operator, LLC 100 %

December 20, 2018 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 14, 2018 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-

December 11, 2018 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 6, 2018 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5

November 13, 2018 EX-10.1

Filed herewith

Exhibit 10.1 FIRST AMENDMENT TO LOAN AGREEMENT THIS FIRST AMENDMENT TO LOAN AGREEMENT (this “Amendment”) is effective as of September 30, 2018 (the “Effective Date”), by and among CWI 2 OP LP, a Delaware limited partnership (“Borrower”), and W. P. Carey Inc., a Maryland corporation (“Lender”). RECITALS A.Borrower is the maker of that certain Amended, Restated and Consolidated Promissory Note (the

November 13, 2018 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q þ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2018 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 CAREY WATERMARK

August 14, 2018 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q þ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2018 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 CAREY WATERMARK INVES

June 27, 2018 EX-3.1

Amended and Restated Bylaws of Carey Watermark Investors 2 Incorporated

Exhibit 3.1 CAREY WATERMARK INVESTORS 2 INCORPORATED AMENDED AND RESTATED BYLAWS ARTICLE I OFFICES Section 1. Principal Office. The principal office of the Corporation in the State of Maryland shall be located at such place as the Board of Directors may designate. Section 2. Additional Offices. The Corporation may have additional offices, including a principal executive office, at such places as t

June 27, 2018 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 21, 2018 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5765

May 14, 2018 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q þ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2018 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 CAREY WATERMARK INVE

April 20, 2018 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Ame

Use these links to rapidly review the document Table of Contents Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

April 12, 2018 EX-99.1

CONSENT OF CBRE, INC. DBA CBRE HOTELS

Exhibit 99.1 CONSENT OF CBRE, INC. DBA CBRE HOTELS Carey Watermark Investors 2 Incorporated: We hereby consent to the references to our firm and description of our role in the appraisal of the fair market value of Carey Watermark Investors 2 Incorporated?s (the ?Company?) real estate portfolio as of December 31, 2017, included in this Current Report on Form 8-K, as amended, and incorporated by ref

April 12, 2018 EX-99.2

CONSENT OF ROBERT A. STANGER & CO., INC.

Exhibit 99.2 CONSENT OF ROBERT A. STANGER & CO., INC. Carey Watermark Investors 2 Incorporated: We hereby consent to the references to our firm and description of our role in the estimates of the fair market value of the Carey Watermark Investors 2 Incorporated’s (the “Company”) mortgage debt encumbering its real estate portfolio as of December 31, 2017, included in this Current Report on Form 8-K

April 12, 2018 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 11, 2018 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-576

March 27, 2018 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K þ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2017 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 CAREY WATERMARK INVESTORS

March 27, 2018 EX-21.1

Filed herewith

Exhibit 21.1 CAREY WATERMARK INVESTORS 2 INCORPORATED LIST OF REGISTRANT SUBSIDIARIES Name of Subsidiary Ownership State or Country of Incorporation Arlington 2 Hotel Operator, LLC 100 % Delaware Atlanta Peachtree 2 Hotel Mezzanine Operator, LLC 100 % Delaware Atlanta Peachtree 2 Hotel Operator, LLC 100 % Delaware Bellevue 2 Hotel Operator, Inc. 95 % Delaware Charlotte 2 Hotel Operator, LLC 100 %

December 18, 2017 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 14, 2017 Carey Watermark

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 14, 2017 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-

November 15, 2017 POS AM

As filed with the Securities and Exchange Commission on November 15, 2017

As filed with the Securities and Exchange Commission on November 15, 2017 Registration No.

November 13, 2017 EX-10.2

Incorporated by reference to Exhibit 10.2 to Quarterly Report on Form 10-Q for the quarter ended September 30, 2017, filed on November 13, 2017

Exhibit 10.2 PAYMENT GUARANTY THIS PAYMENT GUARANTY (this “Guaranty”) is made as of October 19, 2017 by CAREY WATERMARK INVESTORS 2 INC., a Maryland corporation having an address at 50 Rockefeller Plaza, 2nd Floor, New York, NY 10020 (“Guarantor”), in favor of W. P. CAREY INC., a Maryland corporation, having an address at 50 Rockefeller Plaza, 2nd Floor, New York, NY 10020 (“Lender”). RECITALS A.

November 13, 2017 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q þ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2017 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 CAREY WATERMARK

November 13, 2017 EX-10.4

Incorporated by reference to Exhibit 10.4 to Quarterly Report on Form 10-Q for the quarter ended September 30, 2017, filed on November 13, 2017

Exhibit 10.4 PROMISSORY NOTE $25,000,000.00 New York, New York October 19, 2017 FOR VALUE RECEIVED CWI 2 OP, LP, a Delaware limited partnership, having an address at 50 Rockefeller Plaza, 2nd Floor, New York, NY 10020 (referred to herein as ?Borrower?), as maker, hereby unconditionally promises to pay to the order of W. P. Carey Inc., a Maryland corporation, having an address at 50 Rockefeller Pla

November 13, 2017 EX-10.1

Filed herewith

Exhibit 10.1 LOAN AGREEMENT Between W. P. CAREY INC. as Lender and CWI 2 OP, LP as Borrower Dated as of October 19, 2017 TABLE OF CONTENTS Page ARTICLE I DEFINITIONS AND ACCOUNTING TERMS 1 Section 1.1 Certain Defined Terms 1 Section 1.2 Computation of Time Periods 4 Section 1.3 Accounting Terms 5 ARTICLE II AMOUNTS AND TERMS OF THE BORROWINGS 5 Section 2.1 The Commitment 5 Section 2.2 Advances 5 S

November 13, 2017 EX-10.3

Incorporated by reference to Exhibit 10.3 to Quarterly Report on Form 10-Q for the quarter ended September 30, 2017, filed on November 13, 2017

EX-10.3 4 cwi22017q310-qexh103.htm EXHIBIT 10.3 Exhibit 10.3 PLEDGE AND SECURITY AGREEMENT THIS PLEDGE AND SECURITY AGREEMENT (as the same may be amended, restated, replaced, supplemented or otherwise modified from time to time, this “Agreement”), is made as of October 19, 2017, by CWI 2 OP, LP, a Delaware limited partnership, having an address at 50 Rockefeller Plaza, 2nd Floor, New York, NY 1002

November 7, 2017 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 1, 2017 Carey Watermark

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 1, 2017 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5

August 14, 2017 S-3D

As filed with the Securities and Exchange Commission on August 14, 2017

Table of Contents As filed with the Securities and Exchange Commission on August 14, 2017 Registration No.

August 14, 2017 EX-4.1

CAREY WATERMARK INVESTORS 2 INCORPORATED AMENDED AND RESTATED DISTRIBUTION REINVESTMENT PLAN

Exhibit 4.1 CAREY WATERMARK INVESTORS 2 INCORPORATED AMENDED AND RESTATED DISTRIBUTION REINVESTMENT PLAN 1. Participation; Agent. Carey Watermark Investors 2 Incorporated’s Distribution Reinvestment Plan (“Plan”) is available to stockholders of record of the Class A Common Stock, par value $.001 per share, and the Class T Common Stock, par value $.001 per share, (collectively, the “Common Stock”)

August 11, 2017 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q þ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2017 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 CAREY WATERMARK INVES

July 31, 2017 424B3

CAREY WATERMARK INVESTORS 2 INCORPORATED Prospectus Supplement No. 3 Dated July 31, 2017 To Prospectus Dated April 28, 2016

Filed Pursuant to Rule 424(b)(3) File No. 333-196681 CAREY WATERMARK INVESTORS 2 INCORPORATED Prospectus Supplement No. 3 Dated July 31, 2017 To Prospectus Dated April 28, 2016 This prospectus supplement (the ?Prospectus Supplement?) is part of, and should be read in conjunction with, the prospectus of Carey Watermark Investors 2 Incorporated, dated April 28, 2016 (as amended or supplemented, the

June 23, 2017 424B3

CAREY WATERMARK INVESTORS 2 INCORPORATED Prospectus Supplement No. 2 Dated June 23, 2017 To Prospectus Dated April 28, 2016

424B3 1 a2232525z424b3.htm 424B3 QuickLinks - Click here to rapidly navigate through this document Filed Pursuant to Rule 424(b)(3) File No. 333-196681 CAREY WATERMARK INVESTORS 2 INCORPORATED Prospectus Supplement No. 2 Dated June 23, 2017 To Prospectus Dated April 28, 2016 This prospectus supplement (the "Prospectus Supplement") is part of, and should be read in conjunction with, the prospectus

June 22, 2017 8-K

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 22, 2017 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5765

June 19, 2017 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 13, 2017 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5765

May 16, 2017 424B3

CAREY WATERMARK INVESTORS 2 INCORPORATED Prospectus Supplement No. 1 Dated May 16, 2017 To Prospectus Dated April 27, 2017

Table of Contents Filed Pursuant to Rule 424(b)(3) File No. 333-196681 CAREY WATERMARK INVESTORS 2 INCORPORATED Prospectus Supplement No. 1 Dated May 16, 2017 To Prospectus Dated April 27, 2017 This prospectus supplement (the “Prospectus Supplement”) is part of, and should be read in conjunction with, the prospectus of Carey Watermark Investors 2 Incorporated, dated April 27, 2017 (as amended or s

May 12, 2017 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q þ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2017 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 CAREY WATERMARK INVE

April 28, 2017 424B3

CAREY WATERMARK INVESTORS 2 INCORPORATED $1,400,000,000 of Common Stock ? Class A Shares and Class T Shares $600,000,000 of Common Stock ? Distribution Reinvestment Plan

Table of Contents Filed Pursuant to Rule 424(b)(3) File No. 333-196681 Prospectus CAREY WATERMARK INVESTORS 2 INCORPORATED $1,400,000,000 of Common Stock ? Class A Shares and Class T Shares $600,000,000 of Common Stock ? Distribution Reinvestment Plan This is our initial public offering of our Class A Shares and Class T Shares, which we refer to collectively as our common stock. The share classes

April 14, 2017 POS AM

As Filed with the Securities and Exchange Commission on April 13, 2017

Use these links to rapidly review the document TABLE OF CONTENTS Table of Contents As Filed with the Securities and Exchange Commission on April 13, 2017 Registration No.

April 13, 2017 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Ame

Use these links to rapidly review the document Table of Contents Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

April 12, 2017 EX-99.1

CONSENT OF CBRE, INC. DBA CBRE HOTELS

Exhibit 99.1 CONSENT OF CBRE, INC. DBA CBRE HOTELS Carey Watermark Investors 2 Incorporated: We hereby consent to the references to our firm and description of our role in the appraisal of the fair market value of Carey Watermark Investors 2 Incorporated’s (the “Company”) real estate portfolio as of December 31, 2016, included in this Current Report on Form 8-K, as amended (the “Current Report”),

April 12, 2017 EX-99.2

CONSENT OF ROBERT A. STANGER & CO., INC.

Exhibit 99.2 CONSENT OF ROBERT A. STANGER & CO., INC. Carey Watermark Investors 2 Incorporated: We hereby consent to the references to our firm and description of our role in the estimates of the fair market value of the Carey Watermark Investors 2 Incorporated’s (the “Company”) mortgage debt encumbering its real estate portfolio as of December 31, 2016, included in this Current Report on Form 8-K

April 12, 2017 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 12, 2017 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-576

March 31, 2017 424B3

CAREY WATERMARK INVESTORS 2 INCORPORATED Prospectus Supplement No. 10 Dated March 31, 2017 To Prospectus Dated April 28, 2016

Table of Contents Filed Pursuant to Rule 424(b)(3) File No. 333-196681 CAREY WATERMARK INVESTORS 2 INCORPORATED Prospectus Supplement No. 10 Dated March 31, 2017 To Prospectus Dated April 28, 2016 This prospectus supplement (the “Prospectus Supplement”) is part of, and should be read in conjunction with, the prospectus of Carey Watermark Investors 2 Incorporated, dated April 28, 2016 (as amended o

March 28, 2017 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 24, 2017 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-576

March 23, 2017 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K þ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2016 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 CAREY WATERMARK INVESTORS

March 23, 2017 EX-21.1

CAREY WATERMARK INVESTORS 2 INCORPORATED LIST OF REGISTRANT SUBSIDIARIES Name of Subsidiary Ownership State or Country of Incorporation Arlington 2 Hotel Operator, LLC 100 % Delaware Atlanta Peachtree 2 Hotel Mezzanine Operator, LLC 100 % Delaware At

Exhibit 21.1 CAREY WATERMARK INVESTORS 2 INCORPORATED LIST OF REGISTRANT SUBSIDIARIES Name of Subsidiary Ownership State or Country of Incorporation Arlington 2 Hotel Operator, LLC 100 % Delaware Atlanta Peachtree 2 Hotel Mezzanine Operator, LLC 100 % Delaware Atlanta Peachtree 2 Hotel Operator, LLC 100 % Delaware Bellevue 2 Hotel Operator, Inc. 95 % Delaware CWI 2 Arlington Hotel, LLC 100 % Delaw

March 20, 2017 EX-99.1

Contents Independent auditor's report 1 Financial statements Combined consolidated balance sheets 2 Combined consolidated statements of operations 3 Combined consolidated statements of changes in equity 4 Combined consolidated statements of cash flow

Exhibit 99.1 Ritz-Carlton San Francisco Combined consolidated Financial Report Nine months Ended September 30, 2016 and Years Ended December 31, 2015 and 2014 Includes accounts of: RC SF Mezz Borrower LLC RC SF Mezz Lessee LLC Contents Independent auditor's report 1 Financial statements Combined consolidated balance sheets 2 Combined consolidated statements of operations 3 Combined consolidated st

March 20, 2017 8-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 30, 2016 CAREY WATERMA

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 30, 2016 CAREY WATERMARK INVESTORS 2 INCORPORATED (Exact name of registrant as specified in its charter) 000-55461 46-5765413 (Commission File Number) (I.R.S. Employer Iden

March 20, 2017 EX-99.2

CAREY WATERMARK INVESTORS 2 INCORPORATED UNAUDITED PRO FORMA CONDENSED CONSOLIDATED FINANCIAL INFORMATION

Exhibit 99.2 CAREY WATERMARK INVESTORS 2 INCORPORATED UNAUDITED PRO FORMA CONDENSED CONSOLIDATED FINANCIAL INFORMATION Our pro forma condensed consolidated balance sheet as of September 30, 2016 has been prepared as if the significant transaction during the fourth quarter of 2016 (noted herein) had occurred as of September 30, 2016. Our pro forma condensed consolidated statements of operations for

March 6, 2017 424B3

CAREY WATERMARK INVESTORS 2 INCORPORATED Prospectus Supplement No. 9 Dated March 6, 2017 To Prospectus Dated April 28, 2016

QuickLinks - Click here to rapidly navigate through this document Filed Pursuant to Rule 424(b)(3) File No.

March 6, 2017 8-K

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 28, 2017 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-

February 1, 2017 424B3

CAREY WATERMARK INVESTORS 2 INCORPORATED Supplement No. 8 dated February 1, 2017 to the Prospectus dated April 28, 2016

Use these links to rapidly review the document TABLE OF CONTENTS TABLE OF CONTENTS TABLE OF CONTENTS 3 Table of Contents Filed pursuant to Rule 424(b)(3) File No.

January 18, 2017 POS AM

As Filed with the Securities and Exchange Commission on January 18, 2017

Use these links to rapidly review the document TABLE OF CONTENTS TABLE OF CONTENTS TABLE OF CONTENTS 3 Table of Contents As Filed with the Securities and Exchange Commission on January 18, 2017 Registration No.

January 11, 2017 424B3

CAREY WATERMARK INVESTORS 2 INCORPORATED Supplement No. 7 dated January 10, 2017 to the Prospectus dated April 28, 2016

Use these links to rapidly review the document TABLE OF CONTENTS TABLE OF CONTENTS TABLE OF CONTENTS 3 Table of Contents Filed pursuant to Rule 424(b)(3) File No.

January 6, 2017 EX-10.1

Incorporated by reference to Exhibit 10.1 to Current Report on Form 8-K filed on January 6, 2017

Exhibit 10.1 PURCHASE AND SALE AGREEMENT AMONG RC SF OWNER LLC, AS SELLER, AND CWI 2 SAN FRANCISCO HOTEL, LP, AS PURCHASER December 28, 2016 TABLE OF CONTENTS Page ARTICLE I SALE 1 1.1 Real Property 1 1.2 Personal Property 1 1.3 Contracts, Equipment Leases and Leases 2 1.4 Bookings 2 ARTICLE II PURCHASE PRICE 3 2.1 Purchase Price 3 2.2 Allocation of Purchase Price 3 2.3 Deposit 3 2.4 Independent C

January 6, 2017 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 30, 2016 Carey Watermark

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 30, 2016 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-

December 14, 2016 CORRESP

ToniAnn Sanzone

ToniAnn Sanzone Chief Financial Officer TEL +1-212-492-1191 FAX +1-212-492-8922 tsanzone@wpcarey.

December 12, 2016 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 7, 2016 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5

November 21, 2016 CORRESP

ToniAnn Sanzone

ToniAnn Sanzone Chief Financial Officer TEL +1-212-492-1191 FAX +1-212-492-8922 tsanzone@wpcarey.

November 17, 2016 424B3

CAREY WATERMARK INVESTORS 2 INCORPORATED Prospectus Supplement No. 6 Dated November 17, 2016 To Prospectus Dated April 28, 2016

Filed Pursuant to Rule 424(b)(3) File No. 333-196681 CAREY WATERMARK INVESTORS 2 INCORPORATED Prospectus Supplement No. 6 Dated November 17, 2016 To Prospectus Dated April 28, 2016 This prospectus supplement (the “Prospectus Supplement”) is part of, and should be read in conjunction with, the prospectus of Carey Watermark Investors 2 Incorporated, dated April 28, 2016 (as amended or supplemented,

November 14, 2016 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q þ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2016 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 CAREY WATERMARK

October 21, 2016 POS AM

As Filed with the Securities and Exchange Commission on October 21, 2016

Use these links to rapidly review the document TABLE OF CONTENTS Table of Contents As Filed with the Securities and Exchange Commission on October 21, 2016 Registration No.

October 21, 2016 CORRESP

Kathleen L. Werner

Kathleen L. Werner Partner TEL +1 212 878 8526 FAX +1 212 878 8375 [email protected] October 21, 2016 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549-0404 Mr. Coy Garrison: On behalf of our client, Carey Watermark Investors 2 Incorporated, a Maryland corporation (the “Company”), we transmit for fi

October 6, 2016 EX-99.2

Contents Financial statements Balance sheet (unaudited) 1 Statements of operations (unaudited) 2 Statements of changes in member's equity (unaudited) 3 Statements of cash flows (unaudited) 4 Notes to financial statements (unaudited) 5-9

Exhibit 99.2 HEI La Jolla LLC Marriott La Jolla Financial Report For the Three Months Ended March 31, 2016 and 2015 (Unaudited) Contents Financial statements Balance sheet (unaudited) 1 Statements of operations (unaudited) 2 Statements of changes in member's equity (unaudited) 3 Statements of cash flows (unaudited) 4 Notes to financial statements (unaudited) 5-9 HEI La Jolla LLC Balance Sheet (Una

October 6, 2016 EX-99.1

Contents Independent auditor's report 1-2 Financial statements Balance sheets 3 Statements of operations 4 Statements of changes in member's equity 5 Statements of cash flows 6 Notes to financial statements 7-11 Independent Auditor's Report

Exhibit 99.1 HEI La Jolla LLC Marriott La Jolla Financial Report Years Ended December 31, 2015 and 2014 Contents Independent auditor's report 1-2 Financial statements Balance sheets 3 Statements of operations 4 Statements of changes in member's equity 5 Statements of cash flows 6 Notes to financial statements 7-11 Independent Auditor's Report To the Member HEI La Jolla LLC Report on the Financial

October 6, 2016 8-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 21, 2016 CAREY WATERMARK I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 21, 2016 CAREY WATERMARK INVESTORS 2 INCORPORATED (Exact name of registrant as specified in its charter) 000-55461 46-5765413 (Commission File Number) (I.R.S. Employer Identifi

October 6, 2016 EX-99.3

CAREY WATERMARK INVESTORS 2 INCORPORATED UNAUDITED PRO FORMA CONDENSED CONSOLIDATED FINANCIAL INFORMATION

Exhibit 99.3 CAREY WATERMARK INVESTORS 2 INCORPORATED UNAUDITED PRO FORMA CONDENSED CONSOLIDATED FINANCIAL INFORMATION Our pro forma condensed consolidated balance sheet as of March 31, 2016 has been prepared as if the significant transactions during the second and third quarters of 2016 (noted herein) had occurred as of March 31, 2016. Our pro forma condensed consolidated statements of operations

September 30, 2016 424B3

CAREY WATERMARK INVESTORS 2 INCORPORATED Prospectus Supplement No. 5 Dated September 30, 2016 To Prospectus Dated April 28, 2016

QuickLinks - Click here to rapidly navigate through this document Filed Pursuant to Rule 424(b)(3) File No.

September 28, 2016 EX-99.2

Contents Financial statements Combined balance sheet (unaudited) 1 Combined statements of operations (unaudited) 2 Combined statements of changes in equity (unaudited) 3 Combined statements of cash flows (unaudited) 4 Notes to combined financial stat

Exhibit 99.2 Marriott San Jose Hotel Combined Financial Report For the Three Months Ended March 31, 2016 and 2015 (Unaudited) Includes accounts of: SP6 San Jose Hotel Owner, LLC SP6 San Jose Hotel Lessee, LLC Contents Financial statements Combined balance sheet (unaudited) 1 Combined statements of operations (unaudited) 2 Combined statements of changes in equity (unaudited) 3 Combined statements o

September 28, 2016 8-K/A

Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 13, 2016 CAREY WATERMARK INVESTORS 2 INCORPORATED (Exact name of registrant as specified in its charter) 000-55461 46-5765413 (Commission File Number) (I.R.S. Employer Identifi

September 28, 2016 EX-99.3

CAREY WATERMARK INVESTORS 2 INCORPORATED UNAUDITED PRO FORMA CONDENSED CONSOLIDATED FINANCIAL INFORMATION

Exhibit 99.3 CAREY WATERMARK INVESTORS 2 INCORPORATED UNAUDITED PRO FORMA CONDENSED CONSOLIDATED FINANCIAL INFORMATION Our pro forma condensed consolidated balance sheet as of March 31, 2016 has been prepared as if the significant transactions during the second and third quarters of 2016 (noted herein) had occurred as of March 31, 2016. Our pro forma condensed consolidated statements of operations

September 28, 2016 EX-99.1

Contents Independent auditor's report 1-2 Financial statements Combined balance sheet 3 Combined statement of operations 4 Combined statement of changes in equity 5 Combined statement of cash flows 6 Notes to combined financial statements 7-11 Indepe

Exhibit 99.1 Marriott San Jose Hotel Combined Financial Report Year Ended December 31, 2015 Includes accounts of: SP6 San Jose Hotel Owner, LLC SP6 San Jose Hotel Lessee, LLC Contents Independent auditor's report 1-2 Financial statements Combined balance sheet 3 Combined statement of operations 4 Combined statement of changes in equity 5 Combined statement of cash flows 6 Notes to combined financi

September 23, 2016 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): September 22, 2016 Carey Watermark Investors 2 Incorporated (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46

September 14, 2016 EX-99.2

Contents Financial statements Balance sheet (unaudited) 1 Statements of operations (unaudited) 2 Statements of changes in member's equity (unaudited) 3 Statements of cash flows (unaudited) 4 Notes to financial statements (unaudited) 5-8

EX-99.2 3 cwi220168-kaarlingtonexh992.htm EXHIBIT 99.2 Exhibit 99.2 HEI Rosslyn, LLC Le Méridien Arlington Financial Report For the Three Months Ended March 31, 2016 and 2015(Unaudited) Contents Financial statements Balance sheet (unaudited) 1 Statements of operations (unaudited) 2 Statements of changes in member's equity (unaudited) 3 Statements of cash flows (unaudited) 4 Notes to financial stat

September 14, 2016 EX-99.1

Contents Independent auditor's report 1-2 Financial statements Balance sheets 3 Statements of operations 4 Statements of changes in member's equity 5 Statements of cash flows 6 Notes to financial statements 7-10 Independent Auditor's Report

Exhibit 99.1 HEI Rosslyn, LLC Le Méridien Arlington Financial Report Years Ended December 31, 2015 and 2014 Contents Independent auditor's report 1-2 Financial statements Balance sheets 3 Statements of operations 4 Statements of changes in member's equity 5 Statements of cash flows 6 Notes to financial statements 7-10 Independent Auditor's Report To the Member HEI Rosslyn, LLC Report on the Financ

September 14, 2016 EX-99.3

CAREY WATERMARK INVESTORS 2 INCORPORATED UNAUDITED PRO FORMA CONDENSED CONSOLIDATED FINANCIAL INFORMATION

Exhibit 99.3 CAREY WATERMARK INVESTORS 2 INCORPORATED UNAUDITED PRO FORMA CONDENSED CONSOLIDATED FINANCIAL INFORMATION Our pro forma condensed consolidated balance sheet as of March 31, 2016 has been prepared as if the significant transaction during the second quarter of 2016 (noted herein) had occurred as of March 31, 2016. Our pro forma condensed consolidated statements of operations for the thr

September 14, 2016 8-K/A

Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 28, 2016 CAREY WATERMARK INVESTORS 2 INCORPORATED (Exact name of registrant as specified in its charter) 000-55461 46-5765413 (Commission File Number) (I.R.S. Employer Identifi

August 12, 2016 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2016 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 000-55461 CAREY WATERMARK INVES

August 12, 2016 424B3

CAREY WATERMARK INVESTORS 2 INCORPORATED Prospectus Supplement No. 4 Dated August 12, 2016 To Prospectus Dated April 28, 2016

Table of Contents Filed Pursuant to Rule 424(b)(3) File No. 333-196681 CAREY WATERMARK INVESTORS 2 INCORPORATED Prospectus Supplement No. 4 Dated August 12, 2016 To Prospectus Dated April 28, 2016 This prospectus supplement (the “Prospectus Supplement”) is part of, and should be read in conjunction with, the prospectus of Carey Watermark Investors 2 Incorporated, dated April 28, 2016 (as amended o

August 5, 2016 424B3

CAREY WATERMARK INVESTORS 2 INCORPORATED Supplement No. 3 dated August 5, 2016 to the Prospectus dated April 28, 2016

Use these links to rapidly review the document TABLE OF CONTENTS TABLE OF CONTENTS TABLE OF CONTENTS2 Table of Contents Filed Pursuant to Rule 424(b)(3) File No.

August 4, 2016 CORRESP

CLIFFORD CHANCE US LLP

CLIFFORD CHANCE US LLP 31 WEST 52ND STREET NEW YORK, NY 10019-6131 TEL +1 212 878 8000 FAX +1 212 878 8375 www.

July 27, 2016 EX-10.2

Incorporated by reference to Exhibit 10.2 to the registrant’s Current Report on Form 8-K filed on July 27, 2016

Exhibit 10.2 FIRST AMENDMENT TO AGREEMENT FOR PURCHASE AND SALE OF HOTEL This FIRST AMENDMENT TO AGREEMENT FOR PURCHASE AND SALE OF HOTEL (this “Amendment”) dated as of June 15, 2016, is entered into y and between HEI LA JOLLA LLC, a Delaware limited liability company (“Seller”), and CWI 2 LA JOLLA HOTEL, LP, a Delaware limited partnership (“Purchaser”). W I T N E S S E T H: WHEREAS, Seller and Pu

July 27, 2016 EX-10.1

Incorporated by reference to Exhibit 10.1 to the registrant’s Current Report on Form 8-K filed on July 27, 2016

Exhibit 10.1 Execution Copy AGREEMENT FOR SALE AND PURCHASE OF HOTEL SAN DIEGO MARRIOTT LA JOLLA SAN DIEGO, CALIFORNIA By and Between HEI LA JOLLA LLC, a Delaware limited liability company (?Seller?) and CWI 2 LA JOLLA HOTEL LP, a Delaware limited partnership (?Purchaser?) May 19, 2016 ACTIVE/85506504.17 AGREEMENT FOR SALE AND PURCHASE OF HOTEL Table of Contents Page Article I DEFINITIONS AND REFE

July 27, 2016 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Completion of Acquisition or Disposition of Assets

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 21, 2016 CAREY WATERMARK INVESTORS 2 INCORPORATED (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5765

July 22, 2016 CORRESP

Kathleen L. Werner

Kathleen L. Werner Partner TEL +1 212 878 8526 FAX +1 212 878 8375 [email protected] July 22, 2016 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549-0404 Mr. Coy Garrison: On behalf of our client, Carey Watermark Investors 2 Incorporated, a Maryland corporation (the “Company”), we transmit for filin

July 22, 2016 POS AM

As Filed with the Securities and Exchange Commission on July 22, 2016

Use these links to rapidly review the document TABLE OF CONTENTS TABLE OF CONTENTS TABLE OF CONTENTS2 Table of Contents As Filed with the Securities and Exchange Commission on July 22, 2016 Registration No.

July 19, 2016 EX-10.2

Incorporated by reference to Exhibit 10.2 to the registrant’s Current Report on Form 8-K filed on July 19, 2016

Exhibit 10.2 AMENDMENT TO PURCHASE AND SALE AGREEMENT This AMENDMENT TO PURCHASE AND SALE AGREEMENT (this ?Amendment?) dated as of June 13, 2016, is entered into by and among SP6 SAN JOSE HOTEL OWNER, LLC, a Delaware limited liability company, having an address at 515 S. Flower Street, Suite 3100, Los Angeles, California 90071 (?Fee Seller?), and SP6 SAN JOSE HOTEL LESSEE, LLC, a Delaware limited

July 19, 2016 EX-10.1

Incorporated by reference to Exhibit 10.1 to the registrant’s Current Report on Form 8-K filed on July 19, 2016

Exhibit 10.1 Execution Copy PURCHASE AND SALE AGREEMENT between SP6 SAN JOSE HOTEL OWNER, LLC, and SP6 SAN JOSE HOTEL LESSEE, LLC, collectively, Seller, and CWI 2 SAN JOSE HOTEL, LP, Purchaser Dated as of: May 13, 2016 Property: San Jose Marriott 301 South Market Street San Jose, California 95113 8476/22465-004 current/49894271v13 Execution Copy TABLE OF CONTENTS Page ARTICLE 1 PROPERTY DESCRIPTIO

July 19, 2016 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 13, 2016 CAREY WATERMARK INV

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 13, 2016 CAREY WATERMARK INVESTORS 2 INCORPORATED (Exact Name of Registrant as Specified in its Charter) Maryland (State or Other Jurisdiction of Incorporation) 000-55461 46-5765

July 7, 2016 424B3

CAREY WATERMARK INVESTORS 2 INCORPORATED Prospectus Supplement No. 2 Dated July 7, 2016 To Prospectus Dated April 28, 2016

QuickLinks - Click here to rapidly navigate through this document Filed Pursuant to Rule 424(b)(3) File No.

July 5, 2016 EX-10.2

Incorporated by reference to Exhibit 10.2 to the registrant’s Current Report on Form 8-K filed on July 5, 2016

Exhibit 10.2 FIRST AMENDMENT TO AGREEMENT FOR SALE AND PURCHASE OF HOTEL This FIRST AMENDMENT TO AGREEMENT FOR SALE AND PURCHASE OF HOTEL (this ?Amendment?) dated as of June 24, 2016, is entered into by and between HEI ROSSLYN LLC, a Delaware limited liability company (?Seller?), and CWI 2 ARLINGTON HOTEL, LLC, a Delaware limited liability company (?Purchaser?). W I T N E S S E T H: WHEREAS, Selle

July 5, 2016 EX-10.1

Incorporated by reference to Exhibit 10.1 to the registrant’s Current Report on Form 8-K filed on July 5, 2016

Exhibit 10.1 Execution Draft AGREEMENT FOR SALE AND PURCHASE OF HOTEL LE M?RIDIEN ARLINGTON ARLINGTON, VA By and Between HEI ROSSLYN, LLC, a Delaware limited liability company (?Seller?) and CWI 2 ARLINGTON HOTEL, LLC, a Delaware limited liability company (?Purchaser?) May 26, 2016 Execution Draft AGREEMENT FOR SALE AND PURCHASE OF HOTEL Table of Contents Page Article I DEFINITIONS AND REFERENCES

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