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 Largo
Key Largo Cottages
Key Largo Cottages — boutique self-catering cottages offering free sailing, kayaking, paddle board and bike use in the Florida Keys.
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.
Key West
Fitch Lodge
Fitch Lodge: Your cozy, bohemian Key West basecamp steps from the Historic Seaport.
Key West
The Marker Key West Harbor Resort
The Marker Key West Harbor Resort is a luxury hotel located in Old Town Key West, offering a blend of classic Florida Keys elegance and modern amenities.
Weddings Max
100
Meetings Max
70
Total Space
655 sq ft
Largest Room
655 sq ft
Key Largo
Bungalows Key Largo
All-inclusive adults-only luxury resort in Key Largo with oceanfront bungalows.
Meetings Max
40
Total Space
2800 sq ft
Largest Room
2800 sq ft
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 West
Grand Guesthouse
The Grand Guesthouse is an adults-only bed and breakfast in Key West, offering tropical-themed rooms with private entrances, complimentary continental breakfast, and a central location near Duval Street.
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.
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 Largo
Casa Mar Azul Vacation Rental Properties
Casa Mar Azul offers luxury waterfront vacation rentals in Key Colony Beach, Florida. Enjoy private pools, boat docks, and easy access to the Cabana Club.
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
The Reach Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by Hilton, is a luxurious beachfront resort situated on the island's only private natural sand beach.
Weddings Max
270
Meetings Max
311
Total Space
4700 sq ft
Largest Room
2800 sq ft
The Lower Keys
Looe Key Reef Resort & Dive Center
Looe Key Reef Resort offers beachfront accommodations, daily scuba and snorkeling trips, a full-service dive shop, and a Tiki Bar with live entertainment in the Florida Keys.
Key West
Beachside Resort
Spacious Key West condos with private beach, marina, dining, and island adventures.
Weddings Max
600
Meetings Max
1075
Total Space
11500 sq ft
Largest Room
5675 sq ft
