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
Hyatt Centric Key West Resort and Spa
Hyatt Centric Key West – Waterfront resort with spa, pool, and dining.
Keys Cove Resort | Marathon Rental Homes
Spacious 4-bedroom, 3-bathroom vacation homes in Marathon, FL, featuring private pools, boat slips, and access to a private beach.
Weatherstation Inn
The Weatherstation Inn is an adults-only, historic Key West bed & breakfast tucked away in the gated Truman Annex, offering charming, island-inspired rooms, a sunny terrace, outdoor pool, free continental breakfast, and easy walking access to Duval Street and Mallory Square.
Courtyard by Marriott Key West Waterfront
Courtyard by Marriott Key West Waterfront offers a newly renovated, resort-style experience with no resort or parking fees. Enjoy spacious rooms, a heated outdoor pool, Tiki Bar, and direct access to the Gulf of Mexico.
Captains Quarters
Captain’s Quarters #415 — stylish 2-bedroom waterfront rental in the gated Venture Out community on Cudjoe Key, Florida Keys.
Santa Maria Suites Resort
Luxurious Key West all-suite retreat with kitchens, pools, and Duval vibes.
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.
Florida Keys Vacation Rentals
Florida Keys Vacation Rentals makes finding your perfect Keys getaway easy, featuring a wide selection of beachfront homes and condos from Key Largo to Key West—book securely with a trusted local provider.
Atlantic Bay Resort
Relax in paradise at Atlantic Bay Resort with private beach, waterfront views, and tropical cottages.
Tea Table Key Island Estate & Wedding Venue
Tea Table Key is a spectacular, car-accessible private island estate in Islamorada, spanning over 15 acres and offering complete exclusivity just off the Overseas Highway.
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.
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.
The Retreat in Marathon
Luxury Florida Keys retreat for inspiring executive escapes and unforgettable vacations.
Fitch Lodge
Fitch Lodge: Your cozy, bohemian Key West basecamp steps from the Historic Seaport.
Siesta Motel
Siesta Motel is a clean, family-run property in Marathon offering affordable rooms and efficiencies with kitchenettes, a pool with bar, and a relaxed tropical garden setting.