Investor Presentation November 2023

INVESTOR PRESENTATION NOVEMBER 2023 Significant Value Embedded Within Hotels and Resorts The Company's unique collection of largely independent properties has many embedded valuation benefits that are often overlooked and underappreciated. The Company has continued to take advantage of the disconnect between public and private valuations through strategic dispositions and stock repurchases. Overlooked and Underappreciated Valuation Benefits Unencumbered hotels deliver premium valuations Significant prime retail space Meaningful parking revenue adds to non-room revenue Sizeable club membership revenue contributes to profitability Considerable billboard/media income across our portfolio Future opportunities with underutilized land Unofficial Z Collection monetization Curator Hotel & Resort Collection monetization CURATOR HOTEL & RESORT COLLECTION Close to 90% of our portfolio represents hotels either unencumbered by management, brand or a combination of both; historically, unencumbered properties have transacted at 10-20% higher multiples, given the flexibility provided to potential buyers ~300,000 square feet of prime retail space, currently generating approximately $13.3M in annualized rental income but still with significant vacancies to be leased ~$18.3M of EBITDA generated by parking in the twelve months trailing September 2023 (equating to ~$1,510/key) ~$2.5M to $3.5M per year of net club membership non-refundable initiation fees (amortized over 12 years due to GAAP but collected in cash upfront) ~$2.7M of EBITDA per year generated by billboards at Hotel Ziggy, Mondrian Los Angeles and W Boston, with potential to double in the next few years 300+ acres of underutilized/developable land at Skamania Lodge, Chaminade Resort & Spa, L'Auberge Del Mar, Inn on Fifth and Newport Harbor Island Resort Potential future monetization of the Unofficial Z Collection, which consists of 8 urban lifestyle hotels with 1,569 guestrooms Potential future monetization of Curator Hotel & Resort Collection, which currently consists of 101 member hotels and resorts and is growing Value Creation Initiatives Strategic Dispositions Stock Repurchase Program pebblebrook TRUST Since 2021, the Company has divested more than $700 million in assets in slower-to- recover urban markets to repurpose capital through a combination of strategic acquisitions, stock repurchases and (net) debt pay downs Continuing to take advantage of the disconnect between public and private market valuations, the Company has continued to repurchase more than 11 million shares since Q4 2022, improving our NAV per share by approximately $2.00 28

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