The widest selection of unusual accommodations in Key West, FL

A cabin, a lighthouse, a glamping, your extraordinary stay awaits you

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

Browse Coastal Unique Stays in Key West, FL, United States

Wake up to a fresh sea breeze inside a highly unconventional, artistic home right on the sand at unique seashore stays in Key West, FL, United States.

Affordable, Adventurous Houseboat On-the-water In Key West Florida - Key West, FL
10 1 review

Affordable, Adventurous Houseboat On-the-water In Key West Florida

houseboat, Stock Island
This unique houseboat offers an oceanfront retreat in Cow Key Channel on Stock Island, just minutes by car from Duval Street, providing secluded views with easy access to amenities.
The 19 square meter vessel accommodates two guests with one bedroom and bathroom, featuring a kitchenette, air conditioning, solar and wind power, complimentary kayaks, and fishing opportunities from its private deck.

Discover Prime Family Unique Stays in Key West, FL, United States

Plan an unforgettable coastal escape for the family inside an extraordinary, design-forward property at family-friendly unique island stays in Key West, FL, United States.

Elegant Sailboat Stay - Key West, FL
No reviews

Elegant Sailboat Stay

boat, Stock Island
This luxurious sailboat is moored near Stock Island, Key West, approximately 4 km from Key West International Airport and within 8 km of Ernest Hemingway's Home, Duval Street, and the Southernmost Point.
The 33-square-metre vessel boasts two bedrooms, one bathroom with a whirlpool tub, a fully equipped kitchen, and accommodates up to seven guests, offering access to marina amenities including pools, a gym, restaurants, and bars.
Dole Vita - Key West, FL
No reviews

Dole Vita

boat, Stock Island
The Dole Vita is a boat located in Key West, 4 kilometres from Key West International Airport, offering convenient access to Stock Island.
This air-conditioned vessel accommodates up to seven guests across two bedrooms and two bathrooms, featuring a private swimming pool, terrace, fully equipped kitchen, comfortable seating, complimentary WiFi, and private parking.
40ft Sailboat, 3 Bdrm, 2 Bath, Sleeps Up To 6 - Key West, FL
10 1 review

40ft Sailboat, 3 Bdrm, 2 Bath, Sleeps Up To 6

houseboat, Stock Island
This luxury yacht, docked at Perry Marina on Stock Island, Key West, offers easy access via free shuttle to Key West's attractions such as the Ernest Hemingway Home and Museum and Smathers Beach, with the exact distances not specified.
The 12-metre vessel boasts three staterooms, two bathrooms, sleeping up to six guests, and includes a kitchen with a fridge, air conditioning, and access to Perry Marina's pools, restaurants, fitness centre, and free parking.
Docked In Paradise - Key West, FL
9.0 7 reviews

Docked In Paradise

houseboat, Stock Island
This Stock Island houseboat, situated at The Perry Hotel & Marina in Key West, offers convenient access to downtown Key West via a free shuttle service and is within a reasonable distance of attractions such as the Ernest Hemingway Home and Museum and the Southernmost Point.
The one-bedroom, one-bathroom floating home sleeps four guests and includes air conditioning, a relaxing deck, and access to hotel amenities such as pools, restaurants, and a fitness centre.

Frequently asked questions about unique stays in Key West, FL

  • What clothing or gear is recommended for the climate in Key West, FL?

    Key West is known for its hot and humid weather, so pack light, breathable clothing. You'll want to bring swimwear, sandals, and a hat for sun protection. Don't forget sunscreen, sunglasses, and a light jacket or sweater for the evenings, as it can get chilly at times.
  • What should you know about unique stays in Key West, FL before booking?

    When booking a unique stay in Key West, it's important to consider the location and amenities. Some properties may be located in quieter areas away from the main attractions, while others are in the heart of the action. It's also important to check the reviews and make sure the property is right for your needs.

Popular destinations

Best Key West, FL unusual places with a garden

Luxurious 4-bedroom Catamaran, Sleeps Up To 8 In Delightful Key West - Key West, FL
No reviews

Luxurious 4-bedroom Catamaran, Sleeps Up To 8 In Delightful Key West

houseboat, Stock Island
This Stock Island houseboat offers a luxurious four-bedroom, four-bathroom floating home, conveniently located for exploring Key West attractions such as the Ernest Hemingway Home and Museum and the Southernmost Point, both within a short driving distance.
The 8-guest vessel boasts a fully equipped kitchen, private patio, access to an on-site swimming pool, free Wi-Fi, and laundry facilities, ensuring a comfortable and convenient stay.
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
Awai's Floating Villa is located in Key West's luxury Stock Island village, approximately 8 kilometres from Key West International Airport and 5 kilometres from downtown attractions including Ernest Hemingway's Home and Duval Street.
This luxury houseboat offers 74 square metres of living space, sleeping up to seven guests in two bedrooms and two bathrooms, and boasts a fully equipped kitchen, private patio with sea views, swimming pool access, free Wi-Fi, and on-site parking including an electric vehicle charging station.
Key West Houseboat Haven -Where Ocean Breezes & Margaritas Meet - Key West, FL
No reviews

Key West Houseboat Haven -Where Ocean Breezes & Margaritas Meet

houseboat, Stock Island
This waterside dwelling is located in Key West, a short distance from the Ernest Hemingway Home and Museum and the Southernmost Point, with Fort Zachary Taylor Historic State Park and Smathers Beach also nearby.
This two-bedroom floating home accommodates up to four guests and features air conditioning, internet access, a swimming pool, a garden, and parking, offering a unique escape close to Key West's attractions.
Key West Sailboat Getaway - Key West, FL
9.0 2 reviews

Key West Sailboat Getaway

houseboat, Stock Island
This unique sailboat accommodation is docked at Perry Resort and Marina on Stock Island, just 4.8 kilometres from downtown Key West's attractions, including the Ernest Hemingway Home and Museum and the Southernmost Point.
This houseboat, suitable for up to three guests, offers one bedroom and one bathroom, with onboard amenities such as a kitchenette, mini fridge, coffee maker, and a back deck grill, plus access to resort facilities and discounted charter opportunities.

Browse Unique Stays with a Hot Tub in Key West, FL, United States

Watch the stars over the ocean from the bubbling comfort of a custom outdoor soak at unique island stays featuring a hot tub in Key West, FL, United States.

Tradewinds - Key West, FL
8.9 485 reviews

Tradewinds

house, Key West
This charming house is located just a short walk from the Ernest Hemingway Home and Museum and Duval Street, placing you right in the heart of Key West's lively atmosphere. It has received excellent ratings for location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay.
The property offers a fully equipped kitchen, allowing guests to prepare meals, and features a terrace or balcony where you can relax and enjoy the warm Key West climate. You can also take advantage of amenities like a Jacuzzi, a garden, and parking, making it a perfect choice for those looking for a comfortable and convenient accommodation.
Two Rustic Cottages With Private Hot Tubs & Private Parking - Dogs Ok - Key West, FL
9.2 100 reviews

Two Rustic Cottages With Private Hot Tubs & Private Parking - Dogs Ok

cabin, Key West
This Key West cottage is located in Old Town, a mere 50 metres from Duval Street and within walking distance of the Key West Lighthouse and Ernest Hemingway Home and Museum.
This 151 square metre holiday home accommodates up to 12 guests with 4 bedrooms, 2 bathrooms, a fully equipped kitchen, air conditioning, and a private hot tub, and is also dog-friendly.
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 in Old Town Key West is situated a mere 50 metres from Duval Street, offering convenient walking access to the Southernmost Point and Mallory Square.
The 75 square metre abode accommodates up to six guests, featuring two bedrooms, one bathroom, a fully equipped kitchen, air conditioning, a private garden hot tub, and dedicated parking.
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, situated in Safe Harbour Marina, is a 15-minute drive (approx. 24km) from Key West's city centre.
The three-bedroom, three-bathroom vessel sleeps six, boasts a spacious saloon, teak finishes, two refrigerators, an ice maker, a propane stove and oven, Starlink Wi-Fi, a private dock with grill, and offers optional sailing excursions including sunset sails and reef snorkelling trips.

Compare Pet-Friendly Unique Stays in Key West, FL, United States

Let your pup lounge in the shade of a unique, tropical architectural marvel at pet-friendly unique island stays in Key West, FL, United States.

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
51' Luxury Yacht In Key West - Key West, FL
10 9 reviews

51' Luxury Yacht In Key West

houseboat, Stock Island
Strictly Pleasure | Unique Yacht Stay In The Keys - Key West, FL
10 18 reviews

Strictly Pleasure | Unique Yacht Stay In The Keys

barge, Stock Island
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
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