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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Marathon
Dragonfly Lite
Dragonfly Lite is a secluded 2-bedroom, 1-bathroom vacation home in Marathon, FL, featuring a private heated saltwater pool, outdoor shower, and lush tropical patio. Ideal for couples or small families seeking a tranquil retreat.
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 West
Authors Guesthouse
Stay inspired in a charming Key West guesthouse honoring literary legends.
Islamorada
Heart of Morada
Heart of Morada — luxury 3-bed vacation home with private pool, boat dock & kayaks in the heart of Islamorada, Florida Keys.
Marathon
Dolphin Vacation Rental Homes
Dolphin Vacations offers a curated selection of vacation rentals in Key West and Marathon, FL, including historic homes and modern condos. Properties like Casa Rosa provide private pools and prime locations near Duval Street.
Key West
Alexander Palms Court
Charming Key West oasis with private baths, heated pool, and prime location.
Marathon
Seascape Resort and Marina
Seascape Resort & Marina: serene oceanfront escape with pool, marina, and tropical charm.Seascape Resort & Marina is a tranquil oceanfront retreat in Marathon featuring a private beach, marina access, an outdoor pool, and complimentary kayaks, paddleboards, bicycles, and grilling facilities.
Islamorada
Sands of Islamorada Hotel & Resort
Oceanfront, family-owned Florida Keys escape—discover Sands of Islamorada.
Key West
Best Western Hibiscus Motel
Stay steps from Duval Street in Key West with free breakfast, Wi-Fi, and a heated pool!
Marathon
Coco Plum Vacation Rentals & Real Estate
Luxury Florida Keys vacation rentals with private pools, beach access, and endless ocean adventures await!
Islamorada
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.
Key West
Kona Kai Oasis
Kona Kai Oasis offers boutique guesthouse accommodations with a pool, complimentary bikes, and lush botanical gardens in Key West’s Old Town.
Key West
Eden House Hotel
Eden House Key West is a boutique hotel in the heart of Old Town, offering a heated pool, tropical gardens, and walking distance to Duval Street. Ideal for couples seeking a charming, relaxing retreat.
Marathon
Key By The Sea
Pet-friendly RV/mobile-home community with canal dock access, clubhouse, bathhouse, and oceanfront pavilion.
Key West
Southernmost House
Stay at the iconic Southernmost House, an oceanfront boutique hotel blending historic charm with unforgettable Atlantic views.
Weddings Max
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