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
Marathon
La Casa Habana Vacation Rental
La Casa Habana — private waterfront vacation home on Grassy Key with pool, dock, and gulf views.
Key West
Cabana Club
The Cabana Clubis a premier private swim and beach club offering a range of amenities including a heated/cooled pool, private sandy beach, spa/whirlpool, showering facilities, full bar, and a beach shop.
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.
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
Alexander Palms Court
Charming Key West oasis with private baths, heated pool, and prime location.
Marathon
Tranquility Bay Beachfront Resort
Beachfront paradise in the Florida Keys with villas, pools, spa, and watersports.
Weddings Max
30
Meetings Max
30
Total Space
450 sq ft
Largest Room
450 sq ft
Islamorada
Topsider Resort
Topsider Resort is a unique beachfront retreat in Islamorada, featuring charming octagonal stilted bungalows perched over the bay.
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
Key West
The Saint Hotel
The Saint Hotel Key West, Autograph Collection, is an adults-only boutique hotel located at 417 Eaton Street in Old Town Key West.
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.
Islamorada
The Islands of Islamorada
The Islands of Islamorada is a luxurious, boutique resort nestled in the Upper Florida Keys, offering a serene and upscale escape for travelers seeking both relaxation and adventure.
Weddings Max
50
Key West
Fitch Lodge
Fitch Lodge: Your cozy, bohemian Key West basecamp steps from the Historic Seaport.
Marathon
The Retreat in Marathon
Luxury Florida Keys retreat for inspiring executive escapes and unforgettable vacations.
Meetings Max
16
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.
