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
Caloosa Cove Resort
Caloosa Cove Resort & Marina offers 30 oceanfront suites with kitchens, balconies, and ocean views.
The Lower Keys
Sunshine Key RV Resort & Marina
RV on the Go — mobile home & RV vacation rentals in the Florida Keys, offering turnkey setups where you arrive and relax without hauling your own trailer.
Marathon
Coco Plum Vacation Rentals & Real Estate
Luxury Florida Keys vacation rentals with private pools, beach access, and endless ocean adventures await!
The Lower Keys
Captains Quarters
Captain’s Quarters #415 — stylish 2-bedroom waterfront rental in the gated Venture Out community on Cudjoe Key, Florida Keys.
The Lower Keys
Deer Run on the Atlantic
Charming eco-lodge on Big Pine Key with oceanfront views and Key deer nearby.
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
The Retreat in Marathon
Luxury Florida Keys retreat for inspiring executive escapes and unforgettable vacations.
Meetings Max
16
Key Largo
Dream Bay Resort
Dream Bay Resort is a private, gated resort and wedding venue in Key Largo, offering five charming cottages, a small marina, and breathtaking sunset views over Florida Bay. Ideal for romantic getaways and intimate weddings.
Marathon
Key Colony Beach Vacation
Canal-front Key Colony Beach: sleeps 4, private dock, Cabana Club access.
Islamorada
Topsider Resort
Topsider Resort is a unique beachfront retreat in Islamorada, featuring charming octagonal stilted bungalows perched over the bay.
Key West
Aqua Lodges At Hurricane Hole Marina
Stay in unique dual stateroom houseboats with full kitchens, A/C, and waterfront views!
Marathon
Casa Tua Retreat
Ocean-front canal duplex in Key Colony Beach — bring your boat or rent one!
Key West
Ridley House
Bohemian luxury in a historic Key West mansion with pool and chef's breakfast.
Weddings Max
40
Meetings Max
40
Marathon
Glunz Ocean Beach Hotel & Resort
Glunz Ocean Beach Hotel & Resort offers a beachfront retreat with spacious suites and villas, two oceanfront pools, a private sandy beach, and complimentary water sports equipment—all just steps from Havana Jack’s Oceanside Restaurant.
