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
The Lower Keys
Old Wooden Bridge Guest Cottages & Marina
Old Wooden Bridge Resort & Marina in Big Pine Key offers charming houseboat-style accommodations, a marina, an outdoor pool, and a prime location near the No Name Key Bridge and the National Key Deer Refuge.
Marathon
Key Colony Beach Realty, Inc.
Keys Properties offers curated waterfront rentals and real estate in Key Colony Beach, including over 50 vacation homes with owner-managed care.
Key West
Heron House Court
Heron House Hotels offers two charming, adults-only properties—Heron House and Heron House Court—featuring lush gardens, an outdoor pool, rooftop sundeck, and complimentary continental breakfast.
Islamorada
Casitas at Cheeca Lodge
Cheeca Lodge & Spa is a luxury oceanfront resort in Islamorada, offering upscale accommodations, a 9-hole golf course, spa services, and a private beach with water sports activities. Ideal for couples and families seeking a tranquil Keys getaway.
Key West
The Cabana Inn
The Cabana Inn is an adults-only boutique hotel nestled just one block from Duval Street in Old Town Key West.
Islamorada
The Caribbean Resort
The Caribbean Resort in Islamorada offers 22 private, Caribbean-style homes with ocean views, a beach-entry pool, fishing pier, and complimentary use of bicycles, kayaks, and paddleboards.
Key Largo
Kawama Yacht Club Vacation Rental
Key Largo Rentals offers premier vacation homes—from oceanfront condos to spacious townhouses and luxury villas—ideal for families and water lovers.
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 West
Lighthouse Hotel
Historic charm meets vibrant Key West life steps from Hemingway House and the iconic lighthouse.
Weddings Max
60
Meetings Max
60
Marathon
Grassy Flats Resort & Beach Club
Eco-friendly boutique resort in the Florida Keys with oceanfront dining, water sports, and unique "olde Florida" charm.
The Lower Keys
Sugar Loaf Lodge
Sugarloaf Lodge is a waterfront retreat located at Mile Marker 17 on the Overseas Highway, offering 31 rooms with private patios or balconies overlooking the serene Lower Sugarloaf Sound.
Key West
Tropical Inn
Tropical Inn is an intimate, adults-only boutique inn located on historic Duval Street in Key West.
