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 Key West
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
Colors on White Apartments
Colors on White offers vibrant, apartment-style accommodations in Old Town Key West. Each unit features a private entrance, kitchenette, and access to a pool with a cascading waterfall.
Key West
Hilton Garden Inn Key West
Hilton Garden Inn Key West – The Keys Collection offers modern accommodations with an outdoor pool, fitness center, and The Garden Grille & Bar.
Total Space
391 sq ft
Largest Room
391 sq ft
Key West
Heron House Court
Heron House Hotels offers two charming, adults-only properties—Heron House and Heron House Court—featuring lush gardens, an outdoor pool, rooftop sundeck, and complimentary continental breakfast.
Key West
Wicker Guesthouse
Wicker Guesthouse is a charming, adults-only boutique inn in the heart of Old Town Key West.
Key West
The Capitana Key West
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.
Key West
The Key West Hotel
The Key West Hotel is a boutique retreat offering a blend of historic charm and modern comfort in the heart of Old Town Key West.
Weddings Max
100
Key West
Southernmost Beach Resort
Southernmost Beach Resort & Guesthouses is an oceanfront Key West escape featuring multiple heated pools, beachfront dining, a full-service spa, and lush tropical gardens just steps from Duval Street.
Weddings Max
200
Meetings Max
200
Total Space
1476 sq ft
Largest Room
800 sq ft
Key West
Heron House
Heron House Hotels offers two charming, adults-only properties—Heron House and Heron House Court—featuring lush gardens, an outdoor pool, rooftop sundeck, and complimentary continental breakfast.
Key West
The Cabana Inn
The Cabana Inn is an adults-only boutique hotel nestled just one block from Duval Street in Old Town Key West.
Key West
Historic Hideaways/Key West Realty
Historic Hideaways offers a curated selection of private Key West vacation homes, including cottages, townhomes, and historic residences, many with private pools.
Key West
DoubleTree Resort by Hilton Grand Key - Key West
Located near Smathers Beach, DoubleTree Key West offers family-friendly comfort with newly renovated guestrooms and meeting rooms, resort-style amenities, and a complimentary shuttle to Old Town and Duval Street.
Meetings Max
300
Total Space
8746 sq ft
Largest Room
3402 sq ft
Key West
Pegasus International Hotel
Stay in the heart of Key West with stylish rooms, rooftop pool, and free breakfast!
