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
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
Marathon
Casa De Addison
RentalsInMarathon.com offers stunning vacation homes in the heart of the Florida Keys. Experience breathtaking ocean views, pristine beaches, and vibrant marine life. Perfect for relaxation and adventure, their handpicked rentals provide comfort and...
Key West
New Orleans House
New Orleans House is a gay male-only guesthouse on Duval Street in Key West, featuring a clothing-optional pool, rooftop sundeck, and complimentary happy hour.
Key Largo
The Pelican, Key Largo Waterfront Cottages
The Pelican Key Largo Cottages is a charming waterfront retreat located directly on Florida Bay in Key Largo, offering a serene and tropical escape just an hour from Miami International Airport.
Islamorada
Sunset Inn
Sunset Inn is a renovated boutique hotel in Islamorada offering modern rooms with island-inspired décor, a refreshing outdoor pool, and a central location near local attractions.
Key Largo
Kona Kai Resort, Gallery and Botanic Gardens
Kona Kai Resort offers adults-only boutique accommodations with a private beach, botanical gardens, and art gallery in Key Largo, Florida Keys.
Weddings Max
50
Meetings Max
50
Marathon
Coconut Cay Resort & Marina
Escape to Coconut Cay Resort in Marathon, FL—serene waterfront stays with free bikes, kayaks, and nearby beaches.
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
Ragged Edge Resort & Marina
Ragged Edge Resort & Marina is a charming, family-owned oceanfront retreat in Islamorada, offering a nostalgic "Old Keys" experience with modern comforts.
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.
Key West
Southwinds Motel
Southwinds Motel is a budget-friendly, adults-only hotel in Old Town Key West, offering two outdoor pools, complimentary continental breakfast, and convenient access to Duval Street and the Atlantic Ocean.
Key Largo
Calusa Campground Resort
Calusa Campground Resort & Marina offers RV sites and park model rentals with full hookups, a heated pool, boat ramp, and pet-friendly amenities.
