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
The Lower Keys
Sugarloaf Key RV Resort & Cottages
Sugarloaf Key RV Resort & Cottages is a luxury waterfront retreat in the Florida Keys, offering premium RV sites, pet-friendly glamping options, and a variety of amenities including a heated pool, kayak and paddleboard rentals, and an on-site tiki bar.
Key West
Margaritaville Beach House Key West
Margaritaville Beach House Key West offers laid-back, island-inspired accommodations steps from Smathers Beach, with a lagoon-style pool and on-site bar & grill.
Weddings Max
100
Meetings Max
60
Total Space
4000 sq ft
Largest Room
950 sq ft
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.
Islamorada
Matecumbe Resort
Matecumbe Resort is an oceanfront, family-friendly resort in Islamorada, offering fully equipped suites, a heated pool, private beach, and complimentary kayaks and bicycles.
Marathon
Conch Key Landing
Conch Key Landing — waterfront vacation-rental cottages with private dockage and stunning Florida Bay views on Conch Key.
The Lower Keys
KOA Sugarloaf
Sugarloaf Key KOA Resort offers waterfront RV sites, deluxe cabins, and tent sites with resort-style amenities in the Florida Keys.
Key West
Smallest Bar Inn
The Smallest Bar Inn is an eclectic Duval Street lodging that’s home to Key West’s famously tiny 72 sq ft “Smallest Bar,” offering six cozy accommodation units steps from Old Town’s top attractions.
Key West
Grand Guesthouse
The Grand Guesthouse is an adults-only bed and breakfast in Key West, offering tropical-themed rooms with private entrances, complimentary continental breakfast, and a central location near Duval Street.
The Lower Keys
Coupon Key Island
Coupon Key is a secluded private island located at Mile Marker 27.5 in the Florida Keys, offering breathtaking sunset views, wildlife sightings, and a rooftop bar for a tranquil escape.
Marathon
Florida Keys Villas
Spacious 6-bedroom waterfront villa in Marathon with private pool, spa, dock, and outdoor kitchen. Sleeps 14.
The Lower Keys
Sea View Estate
Sea View Estate is a secluded, oceanfront retreat on Sugarloaf Key featuring two vacation homes, a private dock, pool, tiki bar, and stunning Atlantic views just 15 minutes from Key West.
Key West
The Gardens Hotel & Cottages d'vine Wine Gallery
The Gardens Hotel is a boutique hotel in Key West, offering luxurious accommodations, lush tropical gardens, and a serene atmosphere, just steps from Duval Street.
