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.
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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.
Key Largo
Key Largo Vacation Rental Villas
Experience resort-style fun with the largest pool in the Florida Keys, ocean-view lounging, a speakeasy game room, marina access, and exclusive tennis and pickleball courts—including the Keys’ only indoor pickleball court.
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
Condos in the Keys.com
Oceanfront condos in Islamorada with stunning views, pool, tennis, and beach fun!
Key West
Authors Guesthouse
Stay inspired in a charming Key West guesthouse honoring literary legends.
Marathon
Coconut Cay Resort & Marina
Escape to Coconut Cay Resort in Marathon, FL—serene waterfront stays with free bikes, kayaks, and nearby beaches.
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
Marathon
COCONUT CAY RV PARK
Coconut Cay RV Resort is a boutique family-operated RV park in Marathon, Florida, featuring 25 spacious sites with electric, water, and sewer hookups. Enjoy a heated pool, private sunset beach, and easy access to boat dockage.
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
Islamorada
Nest Villa at Holiday House
The Nest Villa in Islamorada is a private upper-level retreat with two bedrooms, panoramic Florida Bay views, and marina access with free dockage.
Key West
Coconut Palms Villa
Coconut Palms of Key West offers spacious 2- and 3-bedroom beachfront condos at 1800 Atlantic Resort, adjacent to Smathers Beach. Enjoy ocean views, a heated pool, and easy access to water activities.
Islamorada
Mangrove Marina
Full-service marina in Tavernier offering wet slips, dry storage, houseboat rentals & resort amenities in a protected mangrove setting.
Key Largo
Snappers Oceanfront Restaurant & Bar
Snappers Oceanfront Restaurant & Bar in Key Largo serves vibrant waterfront dining with a casual Tiki Bar, live music, dockside seating, boat dockage, and a “Keysy” island vibe.
