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
Rent Key West Vacations
Key West condos and vacation rentals with full kitchens and linens—learn more.
Islamorada
Sun Outdoors Islamorada
Sun Outdoors Islamorada: island-style RV sites and oceanview vacation homes.
Key Largo
Coconut Palm Inn
Coconut Palm Inn is a boutique beachfront hotel on the Florida Bay in Tavernier, offering 450 feet of private beach, 19 stylish rooms and suites, and spectacular sunset views. Ideal for couples and small groups seeking a tranquil Keys retreat.
Islamorada
Islander Resort
Escape to Islander Resort: vibrant Florida Keys stays, beachside dining, and endless adventures!
Meetings Max
1000
Total Space
19000 sq ft
Largest Room
2760 sq ft
Marathon
Happy In The Keys
Luxury waterfront vacation rentals in Marathon & Key Colony Beach, FL. Private pools, docks, and dog-friendly accommodations. Sleeps 8–10.
Islamorada
Freewheeler Vacations
Freewheeler Vacations is the Upper and Middle Keys’ largest and longest-running vacation rental company, offering everything from cozy condos to grand estates, backed by 30+ years of expert service.
Marathon
Marlin Bay Resort & Marina
Marlin Bay Resort & Marina offers luxury vacation homes and a full-service marina with resort-style amenities in Marathon, Florida Keys.
Weddings Max
50
Islamorada
Three Waters Resort & Marina
Escape to Three Waters Resort & Marina for island luxury, ocean views, and endless adventure.Three Waters Resort & Marina, a Tribute Portfolio Resort, is a newly reimagined oceanfront destination in Islamorada, Florida, blending island charm with modern luxury.
Meetings Max
120
Total Space
1680 sq ft
Largest Room
1680 sq ft
Marathon
Royal Plum Club Condominiums
Royal Plum Club: Oceanfront Marathon, FL condos with beach and pool.
Key West
Courtney's Place Historic Cottages
Charming historic cottages in the heart of Old Key West, steps from Duval Street!
Key Largo
Barefeet Vacation Rentals
Barefeet Vacation Rentals — premium vacation homes and condos in the Upper Florida Keys, all along Key Largo’s scenic Overseas Highway.
Key Largo
Bungalows Key Largo
All-inclusive adults-only luxury resort in Key Largo with oceanfront bungalows.
Meetings Max
40
Total Space
2800 sq ft
Largest Room
2800 sq ft
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.
Islamorada
Angler's Reef
Oceanfront 3BR rental in gated community with panoramic views, boat slip, and top Islamorada location.
