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
Aqua Lodges At Hurricane Hole Marina
Stay in unique dual stateroom houseboats with full kitchens, A/C, and waterfront views!
Key Largo
Key Largo Vacation Rental Villas
Experience resort-style fun with the largest pool in the Florida Keys, ocean-view lounging, a speakeasy game room, marina access, and exclusive tennis and pickleball courts—including the Keys’ only indoor pickleball court.
Islamorada
La Siesta Resort & Marina
La Siesta Resort & Villas offers beachfront cottages, suites, and villas with pools, complimentary watersports, and access to three sister resorts in Islamorada.
Key West
Casa 325
Casa 325 is a charming boutique guesthouse in the heart of Key West’s Historic Old Town. Tucked just off lively Duval Street, it offers uniquely designed rooms, a pool, and easy access to shops, dining, and attractions.
Islamorada
Osprey Bay Villa
Osprey Bay Villa is a luxurious 5-bedroom, 3-bathroom bayfront home in Islamorada, offering a private pool, hot tub, deep-water dock, and breathtaking sunset views, accommodating up to 10 guests.
Key Largo
Key Lime Sailing Club and Cottages
Key Lime Sailing Club & Cottages offers a unique, all-inclusive waterfront retreat in Key Largo, featuring self-contained cottages with unlimited sailboat use, kayaks, snorkeling gear, and more.
Key West
Hampton Inn & Suites
Hampton Inn Key West is an oceanfront hotel located just 2 minutes from Key West International Airport, offering free hot breakfast, an outdoor pool with a poolside bar, and complimentary shuttle service to downtown attractions.
Key West
DoubleTree Resort by Hilton Grand Key - Key West
Located near Smathers Beach, DoubleTree Key West offers family-friendly comfort with newly renovated guestrooms and meeting rooms, resort-style amenities, and a complimentary shuttle to Old Town and Duval Street.
Meetings Max
300
Total Space
8746 sq ft
Largest Room
3402 sq ft
Key West
Bayfront Suites Resort & Marina
Bayfront Suites in Key West offers luxury waterfront condos with modern amenities, a rooftop veranda, and a private marina. Perfect for both relaxation and special events.
The Lower Keys
Little Palm Island Resort & Spa
Little Palm Island Resort & Spa is an adults-only private island retreat offering luxury thatched-roof bungalows, gourmet dining, and a world-class spa in the Florida Keys.
Weddings Max
60
Meetings Max
60
Total Space
2480 sq ft
Largest Room
950 sq ft
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.
Marathon
Island Breeze Vacations
Locally owned vacation rental company offering a variety of homes and condos in Marathon, FL. Features include private pools, pet-friendly options, and concierge services.
