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246 Unique places to stay in Key West, FL
9.3 56 reviews
Key West, FL
12/29 – 12/31
$421/nighttotal: $842 (2 )
Elegant Sailboat Stay
1 2
boat , Stock Island
The Susquehanna, a Hunter 380 sailboat, offers unique accommodations at the Perry Hotel and Marina on Stock Island, a short 15-minute shuttle ride from Key West's Old Town. This two-bedroom, one-bathroom vessel sleeps four guests and features a fully equipped galley, air conditioning, and access to the marina's amenities including pools, a fitness center, and complimentary parking.
9.6 5 reviews
Key West, FL
12/29 – 12/31
$1522/nighttotal: $3044 (2 )
Amazing 4 Bdrm, 4 Bath Catamaran - Purpus\n
4 2
houseboat , Stock Island
This Key West houseboat, located less than a mile from Robbie's Marina and the Key West Tropical Forest & Botanical Garden, offers convenient access to dolphin encounters, fishing, and nature walks. This luxurious 4-bedroom, 4-bathroom vessel sleeps 8 guests and boasts a kitchen with a fridge and microwave, air conditioning, a swimming pool, a terrace, a garden, a fitness center, parking, and an on-site arcade/game room.
9.4 3 reviews
Key West, FL
12/29 – 12/31
$1892/nighttotal: $3784 (2 )
5 Cabin Catamaran Sailboat "Devine Sailing" At The Perry Hotel Marina & Resort
5 2
houseboat , Stock Island
This 5-bedroom houseboat accommodation, ideal for travelers seeking a unique waterfront experience in Stock Island, is located in Key West, offering convenient access to the Ernest Hemingway Home and Museum and the Southernmost Point, with Fort Zachary Taylor Historic State Park and Smathers Beach within close proximity. This houseboat features 5 bedrooms and 5 bathrooms, accommodating up to 10 guests with air conditioning and internet provided for comfort, and offers a memorable lodging option enhanced by the tranquil ambiance of the sea breeze.
9.7 466 reviews
Key West, FL
12/29 – 12/31
$450/nighttotal: $900 (2 )
Downtown Studio Half Block From Duval W Parking
1 2
cabin , Key West
This Key West studio apartment is ideally located half a block from Duval Street and one block from the Ernest Hemingway Home, offering easy access to Key West's attractions. The fully furnished unit sleeps two guests and includes a kitchen with a refrigerator, microwave, and dishwasher, plus free parking—a rare amenity in this central location.
Key West, FL
12/29 – 12/31
$1109/nighttotal: $2218 (2 )
Key West Houseboat Haven -Where Ocean Breezes & Margaritas Meet
2 2
houseboat , Stock Island
This unique houseboat experience is located in Key West, offering a memorable escape just a short distance from the Ernest Hemingway Home and Museum and Southernmost Point, with Fort Zachary Taylor Historic State Park and Smathers Beach also nearby. This accommodation features 2 bedrooms, 1 bathroom, and can host up to 4 guests, providing air conditioning, internet, and a swimming pool for a comfortable stay.
Key West, FL
12/29 – 12/31
$786/nighttotal: $1572 (2 )
Delightful 1-bedroom House Boat With Ac In Key West
1 2
houseboat , Stock Island
This unique houseboat offers a waterfront stay in Key West, located conveniently close to the Ernest Hemingway Home and Museum and Southernmost Point, with Fort Zachary Taylor Historic State Park also nearby. This accommodation features 1 bedroom and 1 bathroom for up to 2 guests, includes air conditioning and internet, and provides complimentary kayak use for exploring the marina and waterfront dining options.
10 1 review
Key West, FL
12/29 – 12/31
$713/nighttotal: $1426 (2 )
Stay Aboard Elegant Sailboat
2 2
houseboat , Stock Island
This Hunter 380 sailboat, part of the Perry Hotel and Marina on Stock Island, offers a unique Key West stay with a complimentary shuttle to Old Town, approximately 15 minutes away. This two-bedroom, one-bathroom vessel sleeps four, features air conditioning, internet access, and allows pets; guests enjoy marina and hotel amenities, including pools and a gym, plus easy access to attractions like the Ernest Hemingway Home and Museum.
Key West, FL
07/31 – 08/02
$515/nighttotal: $1030 (2 )
Deluxe Queen At The Curry Mansion - Parking & Heated Pool!
1 2
ryokan , Key West
Ryokan rental. This accommodation is located in Key West. Facilities and services include an iron, a swimming pool and a fridge.
10 9 reviews
Key West, FL
12/29 – 12/31
$2887/nighttotal: $5774 (2 )
Luxurious 40' Sailing Yacht Located In A Beautiful Resort! Vrbo New Offer!
3 2
houseboat , Stock Island
This Stock Island houseboat, docked at the Perry Hotel in Key West, offers convenient access to downtown Key West, the Ernest Hemingway Home and Museum, and Fort Zachary Taylor. The 40-foot yacht, included with the rental, features three staterooms, two bathrooms, sleeps five guests, and includes a fully equipped kitchen, plus access to hotel amenities like two pools and a shuttle; optional excursions range from sunset cruises to multi-day bareboat charters to the Dry Tortugas.
9.0 7 reviews
Key West, FL
10/14 – 10/16
$513/nighttotal: $1026 (2 )
Docked In Paradise
1 2
houseboat , Stock Island
This Key West houseboat, docked at The Perry Hotel & Marina on Stock Island, offers convenient access to downtown via a free shuttle and is near attractions like the Ernest Hemingway Home and Museum and Southernmost Point. The one-bedroom, one-bathroom vessel sleeps four guests and features a private deck, air conditioning, and access to hotel amenities including pools, restaurants, and a fitness center.
9.9 176 reviews
Key West, FL
06/23 – 06/24
$351/nightfor 1 night
Amazing Houseboat With 2nd Floor Observation Deck
1 2
barge , Key West
This Key West houseboat is anchored in shallow waters near Garrison Bight Marina, offering free boat rides to and from the marina. Sleeping up to three guests, it features a full-size bed, futon, and hammock, plus a full bathroom, kitchen with fridge and microwave, and outdoor cooking equipment; a 20% discount on Island to Island Charters is also included.
9.6 288 reviews
Key West, FL
10/30 – 11/04
$589/nighttotal: $2945 (5 )
Happys Houseboat Key West
1 2
houseboat , Key West
This houseboat is located in New Town, Key West, just a short walk from Florida Keys Beaches and within a few miles of Duval Street and Mallory Square. The boat has received excellent ratings for location, cleanliness, and overall user experience. The houseboat has one bedroom and one bathroom, accommodating up to three guests. Amenities include a fully equipped kitchen, air conditioning, a terrace, a garden, and barbecue grills, perfect for enjoying the beautiful Key West weather and scenic views.
Top Family Unique Stays in Key West, FL
These unique stays in Key West, FL are perfect for families, with beaches nearby and one-of-a-kind accommodation for everyone.
9.8 58 reviews
Key West, FL
07/11 – 07/18
$537/nighttotal: $3759 (7 )
Ocean Views! <Br>i Didnt Do It Too
2 4
houseboat , Stock Island
This barge is located on Stock Island, close to Robbie's and Key West Golf Club, offering a unique waterfront experience with stunning bay views. The property has excellent ratings for user experience, location, and cleanliness. The barge features two bedrooms and can comfortably accommodate up to six guests. Amenities include a full kitchen, a spacious living area, a covered patio, a rooftop deck, and a washer and dryer, providing everything you need for a comfortable stay. Guests can enjoy activities such as kayaking, paddleboarding, and boating, exploring the area's abundant marine life.
Key West, FL
01/06 – 01/08
$555/nighttotal: $1110 (2 )
Wake Up On The Water With Southernmost Serenity
2 5
houseboat , Stock Island
This unique waterfront stay is aboard a comfortable yacht docked at the Perry Hotel & Marina on Stock Island, offering a marina experience just under 2 miles from downtown Key West's Duval Street, beaches, and restaurants. This houseboat features 2 bedrooms, 1 bathroom, and sleeps up to 5 guests, with amenities including air conditioning, internet, a full kitchen, and access to resort pools, a fitness center, and on-site water sports.
Key West, FL
10/14 – 10/16
$443/nighttotal: $886 (2 )
Affordable, Adventurous Houseboat On-the-water In Key West Florida
1 2
houseboat , Stock Island
This houseboat is anchored in Cow Key Channel on the eastern side of Key West, offering a waterfront setting just minutes from Duval Street and attractions like the Ernest Hemingway Home and Museum and Southernmost Point. This eco-friendly vessel provides 200 square feet of living space for up to two guests, featuring a kitchenette, air conditioning, and complimentary kayaks, with proximity to Stock Island's golf courses and waterfront activities.
9.3 94 reviews
Key West, FL
10/26 – 10/28
$240/nighttotal: $480 (2 )
The Salty Sunshine Of Key West
1 4
boat , Key West
The Salty Sunshine is anchored in a protected bay just a short distance from Key West's bustling downtown, offering a secluded escape while still being close to all the action. This unique floating accommodation provides a comfortable and relaxing stay for up to six guests. The boat features two bedrooms with queen-sized beds and a sofa sleeper in the living room, along with a fully equipped kitchen, a hot shower, and a spacious top deck perfect for enjoying breathtaking views, stargazing, or simply relaxing.
Best Key West, FL unique accommodations with a garden
10 1 review
Key West, FL
01/06 – 01/08
$540/nighttotal: $1080 (2 )
Wake Up On The Water With Southernmost Serenity
2 5
barge , Stock Island
This unique waterfront yacht accommodation is docked at Perry Hotel & Marina on Stock Island, offering direct access to resort-style amenities and a complimentary shuttle service that runs every half hour to Old Town Key West, located just 3 miles away. This yacht features 2 bedrooms and 1 bathroom, accommodating up to 6 guests with a convertible dinette, and includes a kitchen with a fridge and microwave, air conditioning, a sundeck with a propane grill, and proximity to water sports and dining options like Matt's Stock Island Kitchen & Bar.
10 1 review
Key West, FL
12/29 – 12/31
$840/nighttotal: $1680 (2 )
40ft Sailboat, 3 Bdrm, 2 Bath, Sleeps Up To 6
3 2
houseboat , Stock Island
This 40-foot yacht, docked at Perry Marina on Stock Island, offers easy access to Key West attractions like the Ernest Hemingway Home and Museum and Southernmost Point. The three-bedroom, two-bathroom houseboat sleeps six guests and includes a kitchen with a refrigerator, air conditioning, and access to marina amenities such as pools, restaurants, a fitness center, and free parking and shuttle to downtown Key West.
9.8 352 reviews
Key West, FL
10/14 – 10/16
$833/nighttotal: $1666 (2 )
Tiki Suites~the Grand Tiki~private Water Stay
1 2
barge , Key West
This unique floating accommodation is anchored in Key West harbor, just a short boat ride from Mallory Square and the historic Old Town district. It boasts excellent user, location, and cleanliness ratings, making it a top choice for travelers seeking a special experience. The boat comfortably sleeps two guests in a single bedroom with one bathroom. Amenities include air conditioning, a king-size bed, a Keurig coffee maker, a 50" LED TV, a Blu-ray player, and internet access. Guests can enjoy breathtaking sunsets from the private deck and explore the surrounding waters with the included paddleboards and snorkel gear. A convenient water shuttle service connects the boat to the main island, with free parking at the shuttle dock.
Key West, FL
01/06 – 01/08
$1415/nighttotal: $2830 (2 )
Oceanfront - Break Awai X Away Awai Floating Villas
1 5
boat , Stock Island
This floating villa in Stock Island offers a waterfront experience approximately 5 miles from the Ernest Hemingway Home and Museum and Duval Street. This accommodation provides 900 square feet of living space with four bedrooms and four bathrooms, featuring air conditioning, a swimming pool, a full kitchen, and internet, accommodating up to 14 guests.
Frequently Asked Questions about unique stays in Key West, FL
What are some hidden gems to explore in Key West, FL?
For a taste of local history, head to the Key West Lighthouse and Museum. It's a great place to learn about the island's rich maritime past. If you're looking for something a little more off the beaten path, check out the Fort Zachary Taylor Historic State Park. It has beautiful beaches, a historic fort, and plenty of hiking trails.
What attractions is Key West, FL famous for?
Key West is known for its beautiful beaches, vibrant nightlife, and historical sites. The Southernmost Point of the Continental US is a must-see, and Mallory Square is a great place to catch the sunset. The Hemingway House is also a popular attraction, and you can see the famous six-toed cats that roam the property.
What clothing or gear is recommended for the climate in Key West, FL?
Key West is hot and humid year-round, so pack light, breathable clothing. You'll definitely want a swimsuit, sunglasses, and sunscreen. A hat and light jacket are also good ideas, especially for evenings.
Which neigbourhood offers the best unique stays in Key West, FL?
Old Town is the heart of Key West and has some of the most unique accommodations. You can find charming guesthouses, restored Victorian homes, and even a few boutique hotels. It's also a great place to explore the island's history and culture.
What should you know about unique stays in Key West, FL before booking?
Unique stays in Key West can be more expensive than traditional hotels. It's a good idea to book well in advance, especially if you're traveling during peak season. Also, be sure to read the reviews carefully to get a sense of the property and its location.
Destinations nearby
Find the Best Unique Stays with a Hot Tub in Key West, FL
A private hot tub at your unique stay makes every trip to Key West, FL truly unforgettable after a day by the water.
9.2 100 reviews
Key West, FL
06/28 – 07/02
$1072/nighttotal: $4288 (4 )
Two Rustic Cottages With Private Hot Tubs & Private Parking - Dogs Ok
4 4
cabin , Key West
This pair of cottages is located in Old Town Key West, half a block from Duval Street, and within walking distance of the Key West Lighthouse, The Ernest Hemingway Home and Museum, and Southernmost Point. This dog-friendly vacation rental offers 1630 square feet of space, accommodating up to 12 guests with 4 bedrooms and 2 bathrooms, and features a private hot tub and a full kitchen.
8.8 93 reviews
Key West, FL
06/28 – 07/02
$431/nighttotal: $1724 (4 )
Dog-friendly Cottage With Private Hot Tub & Garden - Great Downtown Location
2 4
cabin , Key West
This Key West cottage is located in Old Town, half a block from Duval Street, and within walking distance of the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park. This 810-square-foot cabin accommodates up to six guests with two bedrooms and one bathroom, featuring a full kitchen, air conditioning, a hot tub, and a private parking space.
9.0 107 reviews
Key West, FL
06/28 – 07/02
$431/nighttotal: $1724 (4 )
Cozy Cottage With Private Hot Tub, Tranquil Garden & Parking - Dogs Ok
2 4
cabin , Key West
This dog-friendly cottage is located in Old Town Key West, just half a block from Duval Street and within walking distance to the Southernmost Point and Mallory Square. This 810 square foot rental accommodates up to six guests with two bedrooms and one bathroom, offering a private hot tub, full kitchen, free WiFi, and private parking.
10 60 reviews
Key West, FL
12/29 – 12/31
$518/nighttotal: $1036 (2 )
Living The Dream Key West Style
3 2
houseboat , Stock Island
This Stock Island houseboat, located at Safe Harbour Marina, is a 15-minute drive from Key West's downtown. The 60-foot Catalina/Morgan Schooner offers three bedrooms, three bathrooms, sleeps six, and features a fully equipped galley, two refrigerators, an ice maker, Starlink WiFi, and a private dock with a grill; optional sunset sails and snorkeling trips are available.
Neighborhoods and points of interest in Key West, FL
Best pet friendly Key West, FL unique stays
Among the 246 accommodations in Key West, FL, here are the 4 best pet friendly unique accommodations
8.0 102 reviews
Key West, FL
07/11 – 07/18
$420/nighttotal: $2940 (7 )
Amsterdam's Curry Mansion Inn
1 4
manor house , Key West
Amsterdam's Curry Mansion Inn is a 3-star Key West bed and breakfast located steps from Duval Street, a 5-minute walk from the Audubon House and Tropical Gardens, 0.3 miles from Mallory Square, and 0.6 miles from the Ernest Hemingway Home and Museum. This Victorian inn offers individually decorated guest rooms with private pools, an outdoor pool, terrace, garden, picnic area, complimentary Wi-Fi, concierge services, a business center, free self-parking, and three meeting rooms.
Key West, FL
01/06 – 01/08
$908/nighttotal: $1816 (2 )
Dream Catamaran - 3 Cabin With Ac, Large Shower, Beautiful Views
3 5
houseboat , Stock Island
This houseboat in Stock Island offers a unique Key West experience, located a 10-minute drive from Smathers Beach, a 12-minute drive from other Florida Keys beaches, an 11-minute walk to Robbie's, and a 4-minute drive to the Key West Tropical Forest and Botanical Garden. This accommodation sleeps up to 5 guests in 3 bedrooms and features air conditioning, internet, and allows pets, providing a comfortable base for exploring nearby attractions like the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
8.7 6 reviews
Key West, FL
01/06 – 01/08
$655/nighttotal: $1310 (2 )
Dream Catamaran
1 5
boat , Stock Island
This 42' Manta sailing catamaran, SeaJaz, offers a private tropical escape docked at the Perry Hotel & Marina in Stock Island, just a short distance from Key West. This boat accommodation for up to 5 guests features 3 bedrooms, 2 bathrooms, Starlink Internet, a kitchen with fridge and freezer, air conditioning, and access to hotel amenities including two swimming pools, with options for customized excursions like snorkeling and sailing lessons.
10 2 reviews
Key West, FL
01/06 – 01/08
$1468/nighttotal: $2936 (2 )
Special Offer! 50 Foot Luxury Sailing Catamaran In Five Star Resort, Key West!
6 5
houseboat , Stock Island
This Key West houseboat on Stock Island offers a unique stay, a 10-minute walk from Robbie's Marina and a 4-minute drive from the Key West Tropical Forest and Botanical Garden. This 1800-square-foot floating home sleeps 12 guests in six bedrooms and six bathrooms, boasting amenities including a full kitchen, pool, parking, Wi-Fi, and laundry facilities, plus nearby access to Key West attractions.
Search Coastal Unique Stays near Key West, FL
Plan an eccentric holiday at coastal unique stays in Key West, FL, situated short distances from regional beach-town boardwalks.
9.6 67 reviews
Key West, FL
12/29 – 12/31
$218/nighttotal: $436 (2 )
Gypsy Soul Sleepaboard
1 2
boat , Stock Island
Explore Unusual Accommodations with Swimming Pool in Key West, FL
Dip in whenever you like; these unique stays near the water in Key West, FL come with a swimming pool on-site for your convenience.
9.7 24 reviews
Key West, FL
12/29 – 12/31
$865/nighttotal: $1730 (2 )
Sentient Waters: 63’ Boat, Free Snorkel Gear, Etc.
2 2
boat , Stock Island
Key West, FL
12/29 – 12/31
$1691/nighttotal: $3382 (2 )
Luxurious 4-bedroom Catamaran, Sleeps Up To 8 In Delightful Key West
4 2
houseboat , Stock Island
10 6 reviews
Key West, FL
12/29 – 12/31
$617/nighttotal: $1234 (2 )
Sentient Waters: 63' Boat With Full Amenities & Sun Deck
