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
Islamorada
Amara Cay Resort
Escape to Amara Cay Resort for luxe island vibes, ocean views, and pure relaxation.
Meetings Max
65
Total Space
575 sq ft
Largest Room
575 sq ft
Key Largo
Seafarer Resort
The Seafarer Resort and Beach is a waterfront cottage motel located directly on Florida Bay in Key Largo, Florida.
Islamorada
The Islands of Islamorada
The Islands of Islamorada is a luxurious, boutique resort nestled in the Upper Florida Keys, offering a serene and upscale escape for travelers seeking both relaxation and adventure.
Weddings Max
50
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
Pegasus International Hotel
Stay in the heart of Key West with stylish rooms, rooftop pool, and free breakfast!
Key West
Smallest Bar Inn
The Smallest Bar Inn is an eclectic Duval Street lodging that’s home to Key West’s famously tiny 72 sq ft “Smallest Bar,” offering six cozy accommodation units steps from Old Town’s top attractions.
Islamorada
Caloosa Cove Resort
Caloosa Cove Resort & Marina offers 30 oceanfront suites with kitchens, balconies, and ocean views.
Marathon
Ocean Breeze RV Park and Marina
Ocean Breeze RV Park & Marina — waterfront RV resort and marina in Marathon, where island camping meets boating access.
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
Duval Inn
Historic charm meets modern comfort at Duval Inn, steps from Key West's vibrant heart.
Key West
The Capitana Key West
The Capitana Key West is a boutique waterfront hotel offering coastal-chic accommodations, a heated pool with a tiki bar, private beach access, and pet-friendly cottages.
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.
Marathon
Vacation Rentals of the Florida Keys
Vacation Rentals Florida Keys — vacation homes, condos & waterfront retreats throughout the Florida Keys, where you’ll find turnkey island stays with amenities, docks and fully‑equipped kitchens.
Key West
Historic Hideaways/Key West Realty
Historic Hideaways offers a curated selection of private Key West vacation homes, including cottages, townhomes, and historic residences, many with private pools.
