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
Hilton Garden Inn Key West
Hilton Garden Inn Key West – The Keys Collection offers modern accommodations with an outdoor pool, fitness center, and The Garden Grille & Bar.
Total Space
391 sq ft
Largest Room
391 sq ft
Marathon
Blackfin Resort & Marina
Escape to Blackfin Resort & Marina in the Florida Keys—relax, fish, boat, and enjoy stunning sunsets!
Islamorada
Heart of Morada
Heart of Morada — luxury 3-bed vacation home with private pool, boat dock & kayaks in the heart of Islamorada, Florida Keys.
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
Irish Ayes Vacation Home Rental
Luxurious 4BR/4BA Keys rental with pool, dock, and canal views.
Key West
Southernmost Inn
The Southernmost Inn is an adults-only boutique hotel in Old Town Key West.
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.
Key West
Orchid Key Inn
Orchid Key Inn is an adults-only boutique hotel on Duval Street, offering stylish rooms, a tropical pool with a hot tub, and a vibrant poolside bar, all within walking distance of Key West's top attractions.
Key West
Heron House
Heron House Hotels offers two charming, adults-only properties—Heron House and Heron House Court—featuring lush gardens, an outdoor pool, rooftop sundeck, and complimentary continental breakfast.
Key West
Atlantis House
Luxurious Key West stays with ocean views, private suites, and island charm.
Marathon
Florida Keys Villas
Spacious 6-bedroom waterfront villa in Marathon with private pool, spa, dock, and outdoor kitchen. Sleeps 14.
Islamorada
Hadley Resort and Marina
Hadley House Resort is a laid-back waterfront hotel in Islamorada, offering rooms with kitchenettes, a private beach, an outdoor pool, and complimentary breakfast, all just steps from the Atlantic Ocean.
Key West
Colocada Vacation Rentals @ Sunrise Suites Resort
Colocada Vacation Rentals specializes in upscale Key West accommodations, offering nightly, weekly, and monthly rentals with VIP-level guest services rooted in generations of local expertise.
Islamorada
Little Basin Villas
Little Basin Villas offers 3-bedroom, 3.5-bathroom waterfront townhomes with private balconies, a heated pool, and boat dockage in Islamorada’s Art District.
