Places to Stay
Claim your corner of The Florida Keys & Key West. Waterfront resorts, tucked-away inns, vacation rentals with a dock out back, campgrounds under the palms...however you like to unwind, there's a place here that gets it. Filter by destination, amenities or whatever matters most and find the spot that turns your trip from planned to perfect. Checkout is the only thing that should stress you out.
Filters
Key West
Havana Cabana
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.
Weddings Max
150
Meetings Max
60
Total Space
1820 sq ft
Largest Room
1100 sq ft
Key West
Smallest Bar Inn
The Smallest Bar Inn is an eclectic Duval Street lodging that’s home to Key West’s famously tiny 72 sq ft “Smallest Bar,” offering six cozy accommodation units steps from Old Town’s top attractions.
Key West
Best Western Hibiscus Motel
Stay steps from Duval Street in Key West with free breakfast, Wi-Fi, and a heated pool!
Key West
Artist House
Stay in a charming Victorian Key West inn with unique rooms, pool, and breakfast.
Key West
Ibis Bay Beach Resort
Ibis Bay Resort offers a fun, colorful Key West escape with a private beach, pool, and onsite restaurant. Perfect for families, couples, and adventure seekers.
Key West
Ocean Key Resort & Spa
Ocean Key Resort & Spa in Key West offers luxury accommodations with Gulf views, a rooftop pool, three waterfront dining options, and a full-service spa, all located at the iconic Zero Duval Street.
Weddings Max
200
Meetings Max
50
Total Space
870 sq ft
Largest Room
850 sq ft
Key West
Key West Historic Inns
Key West Historic Inns — a curated collection of five distinctive, historic properties in Old Town Key West offering boutique stays steeped in island charm.
Weddings Max
100
Meetings Max
25
Key West
Nyah B&B
NYAH Key West is an adults-only hotel offering group-friendly rooms, three pools, complimentary breakfast, and a prime location just steps from Duval Street.
Key West
Santa Maria Suites Resort
Luxurious Key West all-suite retreat with kitchens, pools, and Duval vibes.
Key West
Weatherstation Inn
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.
Key West
Ella's Cottages
Bohemian Key West charm awaits at Ella’s Cottages—stylish, cozy, and full of island spirit.
Key West
Courtyard by Marriott Key West Waterfront
Courtyard by Marriott Key West Waterfront offers a newly renovated, resort-style experience with no resort or parking fees. Enjoy spacious rooms, a heated outdoor pool, Tiki Bar, and direct access to the Gulf of Mexico.
Key West
Caribbean House Hotel
Caribbean House is a charming Bed & Breakfast located in historic Bahama Village, just two blocks from Duval Street.
Key West
Hyatt Vacation Club/Windward Pointe
Hyatt Vacation Club at Windward Pointe is an oceanfront Key West resort with two-bedroom villas, an infinity-edge pool, and Atlantic Ocean views.
