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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Key West
Westwinds Inn
Westwinds Inn is a charming, adults-only Victorian-style boutique hotel located in the Historic Seaport District of Old Town Key West.
Key West
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.
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.
Islamorada
Ragged Edge Resort & Marina
Ragged Edge Resort & Marina is a charming, family-owned oceanfront retreat in Islamorada, offering a nostalgic "Old Keys" experience with modern comforts.
Marathon
Blackfin Resort & Marina
Escape to Blackfin Resort & Marina in the Florida Keys—relax, fish, boat, and enjoy stunning sunsets!
Marathon
Royal Plum Club Condominiums
Royal Plum Club: Oceanfront Marathon, FL condos with beach and pool.
Marathon
Fairfield by Marriott Inn & Suites Marathon Florida Keys
Waterfront hotel in the Florida Keys with pools, marina, and tropical dining.
Key West
Marrero's Guest Mansion
Marrero’s Guest Mansion is an adults-only boutique B&B in Old Town Key West, offering unique rooms in a restored Victorian mansion with a saltwater pool.
Key West
Keys Caribbean Resorts
Explore KeysCaribbean: Expert hotel management and luxury vacation rentals.
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.
Key West
Mansion by the Sea
The Mansion on the Sea (Southernmost House) is an adults-only historic boutique hotel in Key West offering oceanfront rooms, a heated infinity pool, and complimentary breakfast.
Key West
Aqua Lodges At Hurricane Hole Marina
Stay in unique dual stateroom houseboats with full kitchens, A/C, and waterfront views!
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.
Key West
Galleon Resort & Marina
The Galleon Resort & Marina is a waterfront resort in Old Town Key West offering spacious studios and suites with full kitchens or kitchenettes, a private beach, pool, and on-site marina—all just steps from Duval Street.
Key West
Azul Key West
Historic Azul Key West offers a serene, romantic oasis just steps from vibrant downtown.
