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
Pier House Resort & Spa
Pier House Resort & Spa is a historic oceanfront retreat in Old Town Key West, featuring a private white sand beach, full-service spa, three dining venues, and the iconic Chart Room Bar
Weddings Max
120
Meetings Max
120
Total Space
2600 sq ft
Largest Room
2000 sq ft
Key Largo
Key Largo Vacation Home Rentals
Key Largo Vacay — family-friendly vacation rental and lodging service in Key Largo, where waterfront amenities and island comfort meet.
Key West
The Bishop Key West
The Bishop Hotel in Key West offers a boutique guesthouse experience across five historic Conch-style properties, blending Old Town charm with modern comfort.
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
La Pensione Inn
La Pensione Inn is an adults-only boutique guesthouse in Old Town Key West, featuring Victorian architecture, a pool, and complimentary breakfast.
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.
Marathon
Courtyard by Marriott Faro Blanco Resort
Waterfront resort in Marathon with two pools, private marina, on-site dining, and event spaces.
Meetings Max
250
Total Space
40000 sq ft
Key West
Simonton Court Historic Inn & Cottages
Simonton Court Historic Inn & Cottages is a tranquil adults-only boutique inn in Old Town Key West, offering four outdoor pools, daily continental breakfast, bike rentals, and lush tropical gardens just steps from Duval Street.
Islamorada
Freewheeler Vacations
Freewheeler Vacations is the Upper and Middle Keys’ largest and longest-running vacation rental company, offering everything from cozy condos to grand estates, backed by 30+ years of expert service.
Islamorada
The Caribbean Resort
The Caribbean Resort in Islamorada offers 22 private, Caribbean-style homes with ocean views, a beach-entry pool, fishing pier, and complimentary use of bicycles, kayaks, and paddleboards.
Marathon
Faro Blanco Resort Marathon Florida Keys, Curio by Hilton
Waterfront resort in Marathon offering coastal luxury, a full-service marina, spa, dining, four pools, and a sister property, Courtyard by Marriott.
Weddings Max
130
Meetings Max
130
Total Space
1820 sq ft
Largest Room
1820 sq ft
Key Largo
Star Properties Destinations
Star Properties Destinations is a vacation rental and property management company in the Florida Keys, offering a variety of accommodations across Key Largo, Islamorada, Marathon, Tavernier, and the Lower Keys.
Key West
Andrew's Inn & Garden Cottages
Charming tropical boutique inn in historic Key West with pool, breakfast, and happy hour.
