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
Speakeasy Inn
The Speakeasy Inn is a historic adults-only guesthouse in Old Town Key West, offering tropical-themed suites, a wraparound porch, and a Rum Bar featuring over 350 rums.
Islamorada
Topsider Resort
Topsider Resort is a unique beachfront retreat in Islamorada, featuring charming octagonal stilted bungalows perched over the bay.
The Lower Keys
Sunshine Key Tiny House Village
Sunshine Key Tiny House Village is a vibrant collection of colorful tiny homes located on Ohio Key, offering a unique and charming way to experience the beauty of the Florida Keys.
Key West
Cabana Club
The Cabana Clubis a premier private swim and beach club offering a range of amenities including a heated/cooled pool, private sandy beach, spa/whirlpool, showering facilities, full bar, and a beach shop.
Key West
Parrot Key Hotel & Villas
Parrot Key Hotel & Villas is a tropical oasis in Key West, offering spacious rooms, suites, and villas surrounded by lush gardens, four outdoor pools, and a complimentary shuttle to Old Town attractions.
Key West
Artist House
Stay in a charming Victorian Key West inn with unique rooms, pool, and breakfast.
Islamorada
Key Lantern
Key Lantern Motel & Blue Fin Inn offers clean, budget-friendly rooms in Islamorada, ideal for Keys adventurers.
Marathon
Tranquility Bay Beachfront Resort
Beachfront paradise in the Florida Keys with villas, pools, spa, and watersports.
Weddings Max
30
Meetings Max
30
Total Space
450 sq ft
Largest Room
450 sq ft
Key West
Simonton Court Historic Inn & Cottages
Simonton Court Historic Inn & Cottages is a tranquil adults-only boutique inn in Old Town Key West, offering four outdoor pools, daily continental breakfast, bike rentals, and lush tropical gardens just steps from Duval Street.
Key West
Alexander's Guesthouse
Charming adult-only Key West retreat with pool, jacuzzi, and vibrant vibes.
Key West
The Bishop Key West
The Bishop Hotel in Key West offers a boutique guesthouse experience across five historic Conch-style properties, blending Old Town charm with modern comfort.
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.
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.
