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
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
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
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.
The Lower Keys
Sugarloaf Key RV Resort & Cottages
Sugarloaf Key RV Resort & Cottages is a luxury waterfront retreat in the Florida Keys, offering premium RV sites, pet-friendly glamping options, and a variety of amenities including a heated pool, kayak and paddleboard rentals, and an on-site tiki bar.
Key Largo
Morning Star Sailing Charters
Morning Star Sailing Charters offers personalized sailing experiences in the Florida Keys, including captained and bareboat charters, sunset cruises, and snorkeling tours.
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
Terra Marine Park
55+ pet-friendly manufactured home community with 23 homes, laundry, fishing, and picnic spaces.
Islamorada
Mar-Key Islamorada
Mar‑Key Islamorada is an exclusive oceanfront private estate in the Florida Keys blending historic Old Florida charm with modern luxury.
Meetings Max
20
Key West
Duval Inn
Historic charm meets modern comfort at Duval Inn, steps from Key West's vibrant heart.
Key Largo
Key Largo Cottages
Key Largo Cottages — boutique self-catering cottages offering free sailing, kayaking, paddle board and bike use in the Florida Keys.
Islamorada
Scuba Town USA
Scuba Town USA in Islamorada offers an all-in-one dive and vacation experience with lodging, dining, pools, a private beach, and access to multiple dive-related businesses, all set within Three Waters Resort & Marina.
Islamorada
Matecumbe Resort
Matecumbe Resort is an oceanfront, family-friendly resort in Islamorada, offering fully equipped suites, a heated pool, private beach, and complimentary kayaks and bicycles.
Key Largo
Hampton Inn Key Largo, FL
Hampton Inn Key Largo is a tropical hotel located on Florida Bay, offering free hot breakfast, an outdoor pool, fitness center, and complimentary WiFi. Guests can enjoy a private beach, boat dock, and easy access to nearby attractions like John Pennekamp Coral Reef State Park.
Key West
Douglas House Hotel
Charming inn in Key West’s Old Town with pool, tropical gardens, and prime location.
