Places to Stay

Cuban vibes meet Key West charm—discover Havana Cabana.Havana Cabana at Key West is a Cuban-inspired hotel featuring the largest pool in Key West, a poolside bar, and a food truck serving Cuban cuisine.

The Weatherstation Inn is an adults-only, historic Key West bed & breakfast tucked away in the gated Truman Annex, offering charming, island-inspired rooms, a sunny terrace, outdoor pool, free continental breakfast, and easy walking access to Duval Street and Mallory Square.

Old Town Suites is a boutique hotel in Key West featuring self-catering apartments with full kitchens, a coffee shop, and a prime location just steps from Duval Street and the Ernest Hemingway Home and Museum.

Charming Key West oasis with private baths, heated pool, and prime location.

The Saint Hotel Key West, Autograph Collection, is an adults-only boutique hotel located at 417 Eaton Street in Old Town Key West.

Cayo Hueso Resorts offers tropically elegant vacation rentals in Old Town Key West. Choose from private 1–3 bedroom bungalows, cottages, and homes, just steps from Duval Street.

Historic Key West stays on Duval Street—family-owned inns.

Luxurious Key West all-suite retreat with kitchens, pools, and Duval vibes.

Simonton Court Historic Inn & Cottages is a tranquil adults-only boutique inn in Old Town Key West, offering four outdoor pools, daily continental breakfast, bike rentals, and lush tropical gardens just steps from Duval Street.

Marrero’s Guest Mansion is an adults-only boutique B&B in Old Town Key West, offering unique rooms in a restored Victorian mansion with a saltwater pool.

The Banyan Resort is a charming, historic all-suite resort nestled in the heart of Old Town Key West

Historic Key West Vacation Rentals offers a curated selection of luxury vacation homes, cottages, and condos in the Key West Historic District.

Luxury 2-story townhome in Key West's premier Truman Annex, near Duval St.

The Capitana Key West is a boutique waterfront hotel offering coastal-chic accommodations, a heated pool with a tiki bar, private beach access, and pet-friendly cottages.

La Pensione Inn is an adults-only boutique guesthouse in Old Town Key West, featuring Victorian architecture, a pool, and complimentary breakfast.