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Key West, FL unique stays
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188 Unique places to stay in Key West, FL

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.

Eddie Griffiths Overnight Charters And  Vacation Rentals!!!!! - Key West, FL
9.4 43 reviews

Eddie Griffiths Overnight Charters And Vacation Rentals!!!!!

houseboat, Stock Island
This houseboat offers a prime waterfront location in downtown Key West, just a short distance from the Ernest Hemingway Home and Museum and Southernmost Point.
This 600-square-foot floating accommodation sleeps up to six guests and features a full kitchen, air conditioning, a swimming pool, and direct fishing access from the dock.
Sleep Aboard & Sail Daily Unique Kw Sailboat Stay - Key West, FL
9.9 99 reviews

Sleep Aboard & Sail Daily Unique Kw Sailboat Stay

boat, Stock Island
This houseboat is located on Stock Island, just a short distance from Stock Island Yacht Club & Marina, Boca Chica Nude Beach, and Boca Chica Beach, offering a peaceful escape from the bustling Key West scene. The houseboat has consistently received excellent ratings for location, cleanliness, and user experience.
The houseboat has 3 bedrooms and can accommodate up to 6 guests. Enjoy a relaxing vacation with amenities including a swimming pool, fitness center, kitchen, and a terrace with stunning waterfront views.

Best Key West, FL unique accommodations with a garden

Tradewinds - Key West, FL
8.9 485 reviews

Tradewinds

house, Key West
Leeward Isle is located in Key West, just a short walk from the Ernest Hemingway Home and Museum and a bit further from Duval Street, offering a quiet respite from the bustling atmosphere of the main attractions. This house has excellent user, location, and cleanliness ratings.
The house is fully equipped with a kitchen, air conditioning, and satellite TV. You can enjoy a terrace or balcony, garden, and parking, as well as a jacuzzi.
Alhambra - Key West, FL
9.7 308 reviews

Alhambra

castle, Key West
This Key West guesthouse is situated in a historic neighborhood, minutes from Duval Street and the attractions of Old Town Key West.
The master suite in a former cigar baron's mansion offers a private entrance, Florida room with mini-refrigerator and Wi-Fi, heated Jacuzzi tub, and shared access to a pool, garden, and outdoor grill; nearby amenities include a convenience store and Cuban coffee shop.
Waterfront & Heated Pool - Away Awai Floating Vill - Key West, FL
9.9 84 reviews

Waterfront & Heated Pool - Away Awai Floating Vill

boat, Stock Island
This luxury houseboat at Perry Marina in Key West offers a unique Stock Island stay, conveniently located near Stock Island's attractions and restaurants.
The two-bedroom, two-bathroom vessel sleeps four guests and features a fully equipped kitchen, in-unit laundry, three decks with waterfront views, and access to Perry Marina's pool.
Resort Chic On The Water! - Key West, FL
9.4 20 reviews

Resort Chic On The Water!

boat, Stock Island
This sailboat accommodation is precisely docked at the Perry Hotel on Stock Island, offering guests easy access to downtown Stock Island via an hourly shuttle.
This roomy vessel features 2 bedrooms, 2 bathrooms, and can host up to 4 guests, boasting 6' 8" of headroom, a spacious cockpit with a small table, and access to the hotel's two pools, three restaurants, and concierge services.

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.

Popular destinations

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.

Living The Dream Key West Style - Key West, FL
10 62 reviews

Living The Dream Key West Style

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.
Dog-friendly Cottage With Private Hot Tub & Garden - Great Downtown Location - Key West, FL
8.8 94 reviews

Dog-friendly Cottage With Private Hot Tub & Garden - Great Downtown Location

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.
Cozy Cottage With Private Hot Tub, Tranquil Garden & Parking - Dogs Ok - Key West, FL
9.0 107 reviews

Cozy Cottage With Private Hot Tub, Tranquil Garden & Parking - Dogs Ok

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.
Tranquil 2br Dog Friendly | Hot Tub | Deck - Key West, FL
8.0 4 reviews

Tranquil 2br Dog Friendly | Hot Tub | Deck

cabin, Key West
This dog-friendly cottage is located in Key West, just half a block from Duval Street, offering walking access to the Southernmost Point and Mallory Square.
This 2-bedroom, 1-bathroom cabin accommodates up to 6 guests and features a private hot tub, a full kitchen with a fridge and microwave oven, air conditioning, complimentary WiFi, and private parking.

Neighborhoods and points of interest in Key West, FL

Best pet friendly Key West, FL unique stays

Among the 188 accommodations in Key West, FL, here are the 4 best pet friendly unique accommodations

Dream Catamaran - 3 Cabin With Ac, Large Shower, Beautiful Views - Key West, FL
No reviews

Dream Catamaran - 3 Cabin With Ac, Large Shower, Beautiful Views

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.
Charming 2-bedroom Boat With Ac In Fabulous Key West, Sleeps Up To 8 People - Key West, FL
10 1 review

Charming 2-bedroom Boat With Ac In Fabulous Key West, Sleeps Up To 8 People

houseboat, Stock Island
This houseboat in Stock Island offers convenient access to Key West attractions, located a 10-minute walk from Robbie's and a 3-minute drive from the Key West Tropical Forest and Botanical Garden.
This pet-friendly houseboat sleeps up to 8 guests in 2 bedrooms and 2 bathrooms, featuring air conditioning, Wi-Fi, a heated swimming pool, and on-site parking.
51' Luxury Yacht In Key West - Key West, FL
10 9 reviews

51' Luxury Yacht In Key West

houseboat, Stock Island
This 51-foot luxury yacht, located in Stock Island, Key West, offers convenient access to the Ernest Hemingway Home and Museum, Southernmost Point, Fort Zachary Taylor Historic State Park, and Smathers Beach.
This four-bedroom, four-bathroom vessel sleeps ten guests and boasts prime waterfront views, promising a unique Key West experience with potential for nearby water activities.
5 Cabin Catamaran Sailboat "Devine Sailing" At The Perry Hotel Marina & Resort - Key West, FL
9.6 4 reviews

5 Cabin Catamaran Sailboat "Devine Sailing" At The Perry Hotel Marina & Resort

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.

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.

Special Offer! 50 Foot Luxury Sailing Catamaran In Five Star Resort, Key West! - Key West, FL
10 4 reviews

Special Offer! 50 Foot Luxury Sailing Catamaran In Five Star Resort, Key West!

houseboat, 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.

3br In Resort Village, Pools, Free Kayak & Shuttle - Key West, FL
9.9 18 reviews

3br In Resort Village, Pools, Free Kayak & Shuttle

boat, Stock Island
Awai's Floating Villa - Houseboat In Luxury Village - Key West, FL
8.7 3 reviews

Awai's Floating Villa - Houseboat In Luxury Village

boat, Stock Island
Waterfront & Heated Pool - Break Awai Floating Villa - Key West, FL
No reviews

Waterfront & Heated Pool - Break Awai Floating Villa

houseboat, Stock Island
43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle To Downtown - Key West, FL
10 6 reviews

43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle To Downtown

houseboat, Stock Island
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