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.

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.

Marathon

American Coastal Vacation Rentals

Luxury Florida Keys rentals with ocean, gulf, and canal views—docks, pools, tennis!

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.

The Lower Keys

Geiger Key Marina & RV Park & Fish Camp

Geiger Key Marina RV Park offers waterfront RV sites with tiki huts, full hookups, and access to kayaking, fishing, and a laid-back fish camp atmosphere—just 10 miles from downtown Key West.

Key West

Blue Flamingo Resort

Blue Flamingo Resort in Key West offers a reimagined getaway with tropical-style rooms, two lively pools with luxe cabanas, and poolside dining at Rum Row and Toasted Coconut.

Key West

Speakeasy Inn

The Speakeasy Inn is a historic adults-only guesthouse in Old Town Key West, offering tropical-themed suites, a wraparound porch, and a Rum Bar featuring over 350 rums.

Key West

Parrot Key Hotel & Villas

Parrot Key Hotel & Villas is a tropical oasis in Key West, offering spacious rooms, suites, and villas surrounded by lush gardens, four outdoor pools, and a complimentary shuttle to Old Town attractions.

Islamorada

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.

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.