Find & Compare Unique Stays in Key West, FL

Experience a unique stay on the waterfront in Key West, just under 1 mile from the Ernest Hemingway Home and Museum and Southernmost Point.
This houseboat offers a one-of-a-kind stay with a sundeck, swimming pool, and direct access to fishing and diving charters.

Experience a unique stay aboard a luxury houseboat at Perry Marina in Stock Island, offering shuttle service just 1.5 miles to Key West Historic Seaport.
This unusual accommodation features two bedrooms, a full kitchen, and a rooftop deck with sunset views for up to four guests.

Experience a unique stay aboard a 42-foot sailboat at The Perry Hotel in Stock Island, just a short shuttle ride from Key West's Southernmost Point and Ernest Hemingway Home and Museum.
This unusual accommodation offers three bedrooms, three bathrooms, and resort amenities including two swimming pools, a kayak, and parking for a memorable island escape.

Docked at Perry Hotel & Marina in Stock Island, this unique stay offers an unusual accommodation experience just 20 minutes from Old Town Key West.
Enjoy an intimate 'yacht lifestyle' with onboard amenities and full access to luxury marina facilities, perfect for a one-of-a-kind stay.

Just 4 minutes by foot from Duval Street, this house offers a unique stay near Key West landmarks like the Ernest Hemingway Home and Museum.
Relax in the Jacuzzi and enjoy the private patio at this unusual accommodation, perfect for exploring Key West.

Just 500 feet from Duval Street, this dog-friendly cabin in Key West offers an unusual accommodation close to the Southernmost Point and Mallory Square.
This cabin sleeps six guests and features a private garden with a Jacuzzi, a full kitchen, and free WiFi for a one-of-a-kind stay.

This Old Town Key West cottage is located half a block from Duval Street, offering easy walking access to the Southernmost Point and Mallory Square.
This dog-friendly cabin, boasting 810 square feet and a private hot tub, provides an unusual accommodation for up to six guests.

Just 15 miles from downtown Key West, this houseboat offers a unique stay in Stock Island's private marina.
Enjoy direct access to Hogfish Restaurant and complimentary paddleboards and kayaks for an unusual accommodation experience.

Experience a unique stay on this houseboat docked at The Perry Hotel & Marina in Stock Island, just 1.5 miles from Key West's Ernest Hemingway Home and Museum.
This houseboat offers a one-of-a-kind stay with waterfront views, accommodating up to four guests with amenities like air conditioning and a swimming pool.

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.

This Key West houseboat offers a prime waterfront location, just a short walk from the Ernest Hemingway Home and Museum and Southernmost Point.
Enjoy this 600 sq ft houseboat, a unique stay accommodating up to six guests with a full kitchen, AC, and fishing opportunities directly from the dock.

Experience a unique stay aboard this sailboat, docked at The Perry Resort and Marina on Stock Island, just a short drive from downtown Key West attractions.
This unusual accommodation offers a kitchenette, air conditioning, and resort amenities, providing an affordable and memorable escape.

Docked in Stock Island, this houseboat offers exclusive 24/7 access to a 40ft yacht and complimentary Perry Hotel amenities, providing a unique stay near Key West attractions like the Ernest Hemingway Home and Museum.
Enjoy a luxurious three-stateroom interior, optional concierge services, and an unforgettable overnight anchoring experience on the ocean for a truly one-of-a-kind stay.

Just 6 minutes on foot from Bayview Park, this Key West houseboat offers a unique stay near the Studios of Key West.
Enjoy 1500 square feet of living space with 3 bedrooms and 2 bathrooms, perfect for up to 10 guests, complete with a kitchen, internet, and air conditioning.