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
Islamorada
Topsider Resort
Topsider Resort is a unique beachfront retreat in Islamorada, featuring charming octagonal stilted bungalows perched over the bay.
Key West
La Pensione Inn
La Pensione Inn is an adults-only boutique guesthouse in Old Town Key West, featuring Victorian architecture, a pool, and complimentary breakfast.
Islamorada
The Last Resort
Islamorada Vacation Rentals offers a curated selection of vacation homes and cottages in the Florida Keys, providing travelers with diverse options for a memorable stay.
Islamorada
Drop Anchor Resort & Marina
Drop Anchor Resort & Marina offers oceanfront accommodations with full kitchens, a heated pool, complimentary kayaks, paddleboards, and bicycles, all set in a tropical garden atmosphere. Ideal for couples and families seeking a relaxing Florida Keys getaway.
Key West
H2O Suites
H2O Suites is an adults-only luxury hotel in Key West, offering 22 contemporary suites with private plunge pools, Italian marble bathrooms, and rooftop pool access, just steps from Duval Street.
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
Islamorada
Caloosa Cove Resort
Caloosa Cove Resort & Marina offers 30 oceanfront suites with kitchens, balconies, and ocean views.
Marathon
La Casa Habana Vacation Rental
La Casa Habana — private waterfront vacation home on Grassy Key with pool, dock, and gulf views.
Marathon
Cocoplum on the Bay
Coco Plum on the Bay — luxurious 4-bedroom waterfront vacation home in Marathon, FL.
Key West
Seascape Tropical Inn
Seascape Tropical Inn is an adults-only, Conch-style bed & breakfast just steps from Duval Street, offering tropical charm, a heated pool and spa, and a complimentary breakfast with Champagne mimosas.
Islamorada
Coastal Vacation Rentals of the Florida Keys
Discover unforgettable Florida Keys vacations with cozy condos to oceanfront estates!
Key West
Southernmost Inn
The Southernmost Inn is an adults-only boutique hotel in Old Town Key West.
The Lower Keys
Sugar Loaf Lodge
Sugarloaf Lodge is a waterfront retreat located at Mile Marker 17 on the Overseas Highway, offering 31 rooms with private patios or balconies overlooking the serene Lower Sugarloaf Sound.
Marathon
Faro Blanco Resort Marathon Florida Keys, Curio by Hilton
Waterfront resort in Marathon offering coastal luxury, a full-service marina, spa, dining, four pools, and a sister property, Courtyard by Marriott.
Weddings Max
130
Meetings Max
130
Total Space
1820 sq ft
Largest Room
1820 sq ft
