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
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.
Islamorada
Sands of Islamorada Hotel & Resort
Oceanfront, family-owned Florida Keys escape—discover Sands of Islamorada.
The Lower Keys
Veterans Dive Center & Retreat
Veterans Dive Center & Retreat — dive shop and veteran-friendly retreat in Summerland Key, Florida.
Islamorada
Condos in the Keys.com
Oceanfront condos in Islamorada with stunning views, pool, tennis, and beach fun!
Key Largo
Tarpon Flats Inn & Marina
Tarpon Flats Inn & Marina is a boutique waterfront retreat in Key Largo, offering five spacious, air-conditioned rooms with kitchenettes, private beach access, and complimentary kayaks for exploring the surrounding waters.
Marathon
Skipjack Resort and Marina
Relax at Skipjack Resort & Marina in the Florida Keys—luxury suites, marina, pool, and fresh seafood!
Marathon
Happy In The Keys
Luxury waterfront vacation rentals in Marathon & Key Colony Beach, FL. Private pools, docks, and dog-friendly accommodations. Sleeps 8–10.
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.
Islamorada
Chesapeake Beach Resort
Escape to paradise at Chesapeake Beach Resort—luxury oceanfront stays in the Florida Keys.
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 Largo
Anchorage Resort & Yacht Club
Relax in spacious waterfront suites and explore the natural beauty of Key Largo at Anchorage Resort & Yacht Club.
Marathon
Casa Clara Condominium
Casa Clara Condos in Key Colony Beach offers oceanfront 2-bedroom, 2-bathroom condos with private balconies, a heated pool, tennis courts, and beach access. Ideal for both short and long-term stays.
Islamorada
Heart of Morada
Heart of Morada — luxury 3-bed vacation home with private pool, boat dock & kayaks in the heart of Islamorada, Florida Keys.
Marathon
Continental Inn
Charming beachfront condos in Key Colony Beach, perfect for a relaxing Florida Keys getaway.
