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
Hyatt Centric Key West Resort and Spa
Hyatt Centric Key West – Waterfront resort with spa, pool, and dining.
Weddings Max
100
Meetings Max
80
Total Space
2369 sq ft
Largest Room
1181 sq ft
Key West
Ridley House
Bohemian luxury in a historic Key West mansion with pool and chef's breakfast.
Weddings Max
40
Meetings Max
40
The Lower Keys
Sugarloaf Key Hotel at KOA Resort
Tropical seaside stay with marina access and on-site dining.
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
Weatherstation Inn
The Weatherstation Inn is an adults-only, historic Key West bed & breakfast tucked away in the gated Truman Annex, offering charming, island-inspired rooms, a sunny terrace, outdoor pool, free continental breakfast, and easy walking access to Duval Street and Mallory Square.
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.
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.
Marathon
Catch of the Day
Oceanlivin offers luxury vacation rentals in Key West, featuring oceanfront properties with private pools, gourmet kitchens, and concierge services. Ideal for travelers seeking a tranquil island retreat.
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.
Islamorada
Angler's Reef
Oceanfront 3BR rental in gated community with panoramic views, boat slip, and top Islamorada location.
Islamorada
Lime Tree Bay Resort
Lime Tree Bay Resort offers beachfront accommodations with multiple heated pools, complimentary watersports, and boat dockage in the Florida Keys.
Key Largo
Florida Keys Luxury Rentals
Florida Keys Luxury Rentals offers high-end vacation homes throughout the Keys, pairing luxury accommodations with personalized concierge, private boating, fishing, gourmet meals, and diving experiences.
Islamorada
Matecumbe Resort
Matecumbe Resort is an oceanfront, family-friendly resort in Islamorada, offering fully equipped suites, a heated pool, private beach, and complimentary kayaks and bicycles.
Key West
Southernmost Inn
The Southernmost Inn is an adults-only boutique hotel in Old Town Key West.
