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
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.
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.
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 West
Tropical Inn
Tropical Inn is an intimate, adults-only boutique inn located on historic Duval Street in Key West.
Marathon
Village at Hawk's Cay Villas & Marina
Village at Hawks Cay Villas, by KeysCaribbean, offers spacious island-style villas—many with private pools, spa tubs, boat dockage, and ocean views—perfect for families or couples seeking a relaxed, Keys-style vacation.
The Lower Keys
Coupon Key Island
Coupon Key is a secluded private island located at Mile Marker 27.5 in the Florida Keys, offering breathtaking sunset views, wildlife sightings, and a rooftop bar for a tranquil escape.
Key Largo
Azul Del Mar
Secluded Key Largo boutique resort with romantic suites, waterfront fun, and stunning sunsets.
Weddings Max
60
Key West
Lunara Bay
Lunara Bay offers 26 luxury oceanfront estates with 6–8 bedrooms, private pools, gourmet kitchens, and concierge services in Key West.
Key West
1800 Atlantic Suites
Luxury Key West condos with ocean views, pool, and top amenities await!
Marathon
Villa Paraiso Vacation Rentals
Villa Paraiso Vacation Rentals offers luxurious, handpicked properties in Marathon and Miami, with personal concierge service and premium comfort.
Marathon
Island Breeze Vacations
Locally owned vacation rental company offering a variety of homes and condos in Marathon, FL. Features include private pools, pet-friendly options, and concierge services.
Marathon
Coco Plum Beach and Tennis Club
Charming family-friendly beachfront resort in Marathon featuring tennis, marina access, and relaxing coastal villas.
Key West
Key West Hideaways
Key West Hideaways: premier Key West vacation rentals with full service.
Marathon
Glunz Ocean Beach Hotel & Resort
Glunz Ocean Beach Hotel & Resort offers a beachfront retreat with spacious suites and villas, two oceanfront pools, a private sandy beach, and complimentary water sports equipment—all just steps from Havana Jack’s Oceanside Restaurant.
