Find & Compare Unique Stays in Key West, FL

Docked at the luxury Perry Hotel in Stock Island, this 3BR/2BA sailboat offers an unusual accommodation experience just a short shuttle ride from Old Town Key West.
Enjoy a unique stay with onboard AC, a kitchen, and full access to hotel amenities like pools and dining, just 3 miles from Key West.

Experience a unique stay on this houseboat in Key West, just a short distance from Southernmost Point and the Ernest Hemingway Home and Museum.
This unusual accommodation offers air conditioning, internet, and a swimming pool for up to 8 guests.

Experience a unique stay aboard a 52-foot sailboat docked on Stock Island, just 5 miles from Key West attractions like the Ernest Hemingway Home and Museum.
This unusual accommodation offers 6 cabins, 6 bathrooms, a private pool, and a full kitchen for up to 23 guests, providing a one-of-a-kind stay.

Experience a unique stay aboard this Hunter 380 Sailboat at the Perry Hotel and Marina in Stock Island, just a 15-minute shuttle ride from Old Town Key West.
This unusual accommodation offers a full gymnasium, two pools, and a complimentary shuttle to explore the area, perfect for a one-of-a-kind stay.

Experience a unique stay on backcountry waters near Key West, offering an off-grid glamping adventure.
This barge accommodates four guests with a kitchen, fridge, and direct access to paddleboarding and fishing.

This unique stay in Key West offers a private pool and terrace, just 2.5 miles from Key West International Airport.
Enjoy this unusual accommodation with air conditioning, free WiFi, and parking, perfect for up to 7 guests.

Docked at Perry Marina in Key West, this houseboat offers a unique stay near the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
Enjoy this 40' yacht, a one-of-a-kind stay for six, with access to two pools, three restaurants, and a fitness center.

Cow Key Channel, a narrow waterway between Key West and Stock Island, offers ocean views and is just over 1 mile from Duval Street for this houseboat.
This 200 sq ft houseboat provides a unique stay for two, featuring a kitchenette, real mattress bed, and complimentary kayaks for exploring the surrounding waters.

Anchored in a protected Key West bay, this boat offers a unique stay just a 15-minute water taxi ride from shore.
Experience unobstructed 360-degree ocean views, a swim ladder, and onsite concierge service for up to six guests in this unusual accommodation.

Experience a unique stay on this 51' power catamaran docked at The Perry Hotel in Stock Island, just 0.5 miles from Key West's Southernmost Point and Ernest Hemingway Home and Museum.
This pet-friendly houseboat offers exclusive use, air conditioning, internet, and four staterooms with private baths, accommodating up to nine guests for an unusual accommodation adventure.

Located in a historic district, this manor house offers convenient access to Key West attractions.
Enjoy a unique stay with complimentary WiFi, a private garden, and an on-site restaurant for an unusual accommodation experience.

Experience a unique stay on this houseboat in Key West, just 500 feet from the Ernest Hemingway Home and Museum and Southernmost Point.
This unusual accommodation offers Starlink Internet, 2 bathrooms, and complimentary water toys, accommodating up to 5 guests.

Anchored offshore Key West, this houseboat offers a secluded tropical paradise, a short pontoon ride from downtown attractions like the Ernest Hemingway Home and Museum.
Experience a unique stay aboard this vintage yacht, featuring 3 bedrooms accommodating up to 8 guests, a full kitchen, and onboard activities like fishing and snorkeling.