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.
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Islamorada
Osprey Bay Villa
Osprey Bay Villa is a luxurious 5-bedroom, 3-bathroom bayfront home in Islamorada, offering a private pool, hot tub, deep-water dock, and breathtaking sunset views, accommodating up to 10 guests.
Islamorada
Island Villa Rental Properties
Discover Island Villa: Luxury Florida Keys getaways await.
Key West
Island House
Island House Key West is a private, adults-only clothing-optional resort with a heated pool, sauna, gym, and 24/7 café/bar in Old Town.
Key West
Speakeasy Inn
The Speakeasy Inn is a historic adults-only guesthouse in Old Town Key West, offering tropical-themed suites, a wraparound porch, and a Rum Bar featuring over 350 rums.
Marathon
Lazy River Vacation
Lazy River Vacation — family-friendly waterfront vacation home in Marathon, where a private heated lazy river pool and 70-ft dock redefine Florida Keys relaxation.
Key West
Southernmost Inn
The Southernmost Inn is an adults-only boutique hotel in Old Town Key West.
Key Largo
Key Largo Cottages
Key Largo Cottages — boutique self-catering cottages offering free sailing, kayaking, paddle board and bike use in the Florida Keys.
Marathon
The Hammocks at Marathon
The Hammocks at Marathon is a tropical resort offering spacious studios and 1- and 2-bedroom suites with full kitchens, balconies, and access to amenities like a heated pool, hot tub, tiki bar, and marina.
Key West
Marquesa Hotel
The Marquesa Hotel is a boutique adults-only retreat in Key West’s historic district, offering lush garden setting, three pools, and the award-winning Café Marquesa.
Key Largo
Tarpon Flats Inn & Marina
Tarpon Flats Inn & Marina is a boutique waterfront retreat in Key Largo, offering five spacious, air-conditioned rooms with kitchenettes, private beach access, and complimentary kayaks for exploring the surrounding waters.
The Lower Keys
Old Wooden Bridge Guest Cottages & Marina
Old Wooden Bridge Resort & Marina in Big Pine Key offers charming houseboat-style accommodations, a marina, an outdoor pool, and a prime location near the No Name Key Bridge and the National Key Deer Refuge.
The Lower Keys
Deer Run on the Atlantic
Charming eco-lodge on Big Pine Key with oceanfront views and Key deer nearby.
Key West
Keys Caribbean Resorts
Explore KeysCaribbean: Expert hotel management and luxury vacation rentals.
Islamorada
Coastal Vacation Rentals of the Florida Keys
Discover unforgettable Florida Keys vacations with cozy condos to oceanfront estates!
Key West
Keys Vacation Rentals
Curated Florida Keys vacation homes and island escapes in Key West, Key Largo, Marathon, and beyond — combining comfort, local charm, and personalized service for every traveler.
