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
Marathon
Banana Bay Resort Marathon
Banana Bay Resort & Marina in Marathon is a laid-back tropical retreat featuring 59 charming guestrooms, a private marina, and complimentary breakfast. Nestled on ten serene Gulf Coast acres, it's the perfect blend of coastal comfort and Florida Keys adventure.
Total Space
1000 sq ft
Islamorada
Chesapeake Beach Resort
Escape to paradise at Chesapeake Beach Resort—luxury oceanfront stays in the Florida Keys.
Key West
Pier House Resort & Spa
Pier House Resort & Spa is a historic oceanfront retreat in Old Town Key West, featuring a private white sand beach, full-service spa, three dining venues, and the iconic Chart Room Bar
Weddings Max
120
Meetings Max
120
Total Space
2600 sq ft
Largest Room
2000 sq ft
Marathon
Jolly Roger RV Resort
Discover Jolly Roger RV Resort: spacious sites, stunning views, and island adventures!
Key Largo
Morning Star Sailing Charters
Morning Star Sailing Charters offers personalized sailing experiences in the Florida Keys, including captained and bareboat charters, sunset cruises, and snorkeling tours.
Key West
Courtyard by Marriott Key West Waterfront
Courtyard by Marriott Key West Waterfront offers a newly renovated, resort-style experience with no resort or parking fees. Enjoy spacious rooms, a heated outdoor pool, Tiki Bar, and direct access to the Gulf of Mexico.
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.
Islamorada
Beach House at Tarpon Point
Luxury oceanfront home with stunning views, private beach, and pool.
Key West
Southernmost Beach Resort
Southernmost Beach Resort & Guesthouses is an oceanfront Key West escape featuring multiple heated pools, beachfront dining, a full-service spa, and lush tropical gardens just steps from Duval Street.
Weddings Max
200
Meetings Max
200
Total Space
1476 sq ft
Largest Room
800 sq ft
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.
Key West
The Capitana Key West
The Capitana Key West is a boutique waterfront hotel offering coastal-chic accommodations, a heated pool with a tiki bar, private beach access, and pet-friendly cottages.
Islamorada
The Moorings Village & Spa
The Moorings Village is a private 18-acre beachfront resort in Islamorada, offering 18 secluded cottages nestled among 800 coconut palms, providing a tranquil and intimate setting.
Key West
Bluewater Key RV Resort
Bluewater Key RV Resort offers luxury RV sites with private tiki huts, lush landscaping, and waterfront access.
Islamorada
Coral Bay Resort
Coral Bay Resort is a waterfront resort in Islamorada offering spacious accommodations, private balconies, a heated pool, and direct access to the bay. Ideal for relaxation and water activities.
