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
Marathon
Rainbow Bend Resort
Rainbow Bend Resort is a family-friendly, oceanfront retreat in Marathon, Florida, offering a private beach, saltwater pool, and hot tub with ocean views.
Marathon
Royal Plum Club Condominiums
Royal Plum Club: Oceanfront Marathon, FL condos with beach and pool.
Marathon
Monte Christo Condos
Monte Christo Condominiums is a luxury oceanfront retreat in Key Colony Beach, offering two- and three-bedroom condos with resort-style amenities.
Key West
Azul Key West
Historic Azul Key West offers a serene, romantic oasis just steps from vibrant downtown.
Key West
New Orleans House
New Orleans House is a gay male-only guesthouse on Duval Street in Key West, featuring a clothing-optional pool, rooftop sundeck, and complimentary happy hour.
Key West
The Reach Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by Hilton, is a luxurious beachfront resort situated on the island's only private natural sand beach.
Weddings Max
270
Meetings Max
311
Total Space
4700 sq ft
Largest Room
2800 sq ft
Islamorada
The Caribbean Resort
The Caribbean Resort in Islamorada offers 22 private, Caribbean-style homes with ocean views, a beach-entry pool, fishing pier, and complimentary use of bicycles, kayaks, and paddleboards.
Key West
Lunara Bay
Lunara Bay offers 26 luxury oceanfront estates with 6–8 bedrooms, private pools, gourmet kitchens, and concierge services in Key West.
Key Largo
Baker's Cay Resort
Baker’s Cay Resort Key Largo — boutique waterfront resort with beach access, watersports, dining and family-friendly amenities in Key Largo, FL.
Meetings Max
400
Total Space
14706 sq ft
Largest Room
3522 sq ft
Key West
Island Time Hospitality Vacation Rentals
Premier short-term vacation homes and waterfront escapes in Key West and the Florida Keys with pool, beach access, pet-friendly stays, and local water activities.
Key West
Key West Hideaways
Key West Hideaways: premier Key West vacation rentals with full service.
Key West
Ella's Cottages
Bohemian Key West charm awaits at Ella’s Cottages—stylish, cozy, and full of island spirit.
Key West
Eden House Hotel
Eden House Key West is a boutique hotel in the heart of Old Town, offering a heated pool, tropical gardens, and walking distance to Duval Street. Ideal for couples seeking a charming, relaxing retreat.
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.
