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 Family-Friendly Unique Stays in Key West, FL

Position your group near local beaches with our distinctive family-friendly unique stays in Key West, FL.

Cozy Retreat With Shared Pool And Parking - Charming Key West Escape - Key West, FL
No reviews

Cozy Retreat With Shared Pool And Parking - Charming Key West Escape

bungalow, Key West
This detached cottage offers a prime downtown Key West location, just a short walk from Duval Street and the Historic Seaport, placing you within 500 metres of attractions such as Fury Water Adventures and Mallory Square's Sunset Celebration. This pet-friendly accommodation, suitable for three guests, features a fully equipped kitchen, air conditioning, and access to a shared swimming pool at the Curry Mansion Inn, with a private parking spot provided.
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.
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.
Luxurious 40' Sailing Yacht! - Key West, FL
9.9 24 reviews

Luxurious 40' Sailing Yacht!

boat, Stock Island
This 40-foot yacht, part of the Perry Hotel & Marina offer in Key West, is docked conveniently near Stock Island, offering easy access to downtown Key West via a complimentary shuttle.
The vessel boasts a three-stateroom layout sleeping five, a fully equipped galley, and access to the hotel's pools, restaurants, and live music; optional excursions include snorkelling, fishing, and dolphin watching, with a unique bareboat charter option to the Dry Tortugas available for longer stays.

Best Key West, FL unusual places with a garden

*Aug/sept Low Rates!* Go Your Own Wave Houseboat - Key West, FL
10 4 reviews

*Aug/sept Low Rates!* Go Your Own Wave Houseboat

barge, Stock Island
This floating retreat, a coastal-themed houseboat, is anchored in the shallow, clear waters of Cow Key Channel, approximately 1.6 kilometres from Old Town and Duval Street.
The houseboat accommodates up to three guests in one bedroom, featuring air conditioning, a kitchen, a garden, a front deck, and a private rooftop deck, with complimentary paddleboat and kayak access for exploring the marine sanctuary and nearby shipwreck.
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 position in Stock Island's city centre, just 500 meters from the Ernest Hemingway Home and Museum and Southernmost Point.
Accommodating up to six guests across 56 square meters, this floating residence features one bedroom and one bathroom, with amenities including a full kitchen, air conditioning, and an on-site swimming pool, with fishing opportunities directly from the dock.
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.
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
This uniquely docked yacht, Strictly Pleasure, is situated at Perry Marina in Stock Island, offering marina views and convenient access to downtown Key West, approximately 8 kilometres away, via the local trolley service.
This pet-friendly accommodation provides two bedrooms, two bathrooms, and can host up to four guests, featuring a galley kitchen with a fridge, freezer, and microwave, air conditioning, a swimming pool, garden, and fitness centre, with parking available directly in front of the vessel.

Frequently asked questions about unique stays in Key West, FL

  • What are some hidden gems to explore in Key West, FL?

    Key West is full of hidden gems! For a unique experience, visit the Key West Lighthouse and Museum, or wander through the Old Town Cemetery, where you'll find quirky and historical headstones. If you're looking for something more adventurous, try kayaking through the mangrove forests of Key West Nature Preserve.
  • What attractions is Key West, FL famous for?

    Key West is known for its laid-back atmosphere and vibrant culture. The Southernmost Point Buoy is a must-see, marking the southernmost point of the continental United States. You can't miss the Ernest Hemingway House, where you'll find six-toed cats roaming the grounds. And, of course, there's always the Key West Butterfly and Nature Conservatory, home to hundreds of tropical butterflies.
  • What clothing or gear is recommended for the climate in Key West, FL?

    Key West is hot and humid year-round. Pack light, breathable clothing like cotton or linen. Don't forget a wide-brimmed hat, sunglasses, and sunscreen for protection from the sun. And bring a light jacket or sweater for the evenings, when it can get a bit chilly.
  • Which neigbourhood offers the best unique stays in Key West, FL?

    Old Town is the heart of Key West and offers a great selection of unique stays. You'll find charming guesthouses, historic homes, and even a few quirky boutiques hotels. The neighbourhood is also close to all the main attractions, so you'll be within walking distance of everything.
  • What should you know about unique stays in Key West, FL before booking?

    Before booking a unique stay in Key West, be sure to check the location and amenities. Some unique stays are located in quiet areas, while others are right in the heart of the action. It's also important to consider the size of the property and the number of guests it can accommodate.

Popular destinations

Search Unusual Places to Stay with a Jacuzzi in Key West, FL

Savour a peaceful evening soak in a hot tub or jacuzzi at these waterside unique stays in Key West, FL.

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.

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

Key West Outpost: Eco-vacation - Key West, FL
9.9 83 reviews

Key West Outpost: Eco-vacation

barge, Key West
The Outpost is a floating cottage located in the tranquil backcountry waters surrounding Key West, just a short distance from the hustle and bustle of the city. It has received excellent ratings for its location, cleanliness, and overall experience.
The barge has two bedrooms and one bathroom, accommodating up to four guests. It features a fully equipped kitchen, air conditioning, solar-powered amenities, and a spacious deck perfect for enjoying the surrounding natural beauty, with activities like paddle boarding, kayaking, and fishing available.
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, situated in Stock Island, Key West, offers convenient access to attractions such as the Ernest Hemingway Home and Museum and the Southernmost Point, all within a reasonable distance.
The four-bedroom, four-bathroom vessel sleeps up to ten guests and boasts upscale amenities, promising a unique Key West experience with potential for water-based activities.
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
This houseboat offers a memorable stay in Key West, located near the Ernest Hemingway Home and Museum and the Southernmost Point, with Fort Zachary Taylor Historic State Park and Smathers Beach within 1.5 kilometres.
This floating accommodation provides two bedrooms, one bathroom, air conditioning, internet, a microwave, and allows pets, with nearby attractions including the Key West Tropical Forest and Botanical Garden and the Sails To Rails Museum at Flagler Station.
Sailboat Stay  Marina Pools  Sleeps 4  Stock Island, Key West - Key West, FL
10 3 reviews

Sailboat Stay Marina Pools Sleeps 4 Stock Island, Key West

houseboat, Stock Island
This Hunter 380 sailboat, part of the Perry Hotel and Marina on Stock Island, offers convenient access to Key West's Old Town via a free 15-minute shuttle service (approx. 8km).
The two-bedroom, one-bathroom vessel sleeps four, includes air conditioning, internet access, and provides access to hotel amenities such as two swimming pools and a gym; nearby attractions include the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.

Discover Unique Stays by the Sea in Key West, FL

Explore beautiful shoreline paths whilst basing your trip at comfortable, coastal unique stays in Key West, FL.

Waterfront Yacht  Sleeps 4  Deck Dining Pools & Bar Access  15 Min Key West - Key West, FL
No reviews

Waterfront Yacht Sleeps 4 Deck Dining Pools & Bar Access 15 Min Key West

houseboat, Stock Island

Top Luxury Unique Stays in Key West, FL

Discover a luxury unique stay on the Key West, FL coast, blending premium quality with singular character.

Happys Houseboat Key West - Key West, FL
9.6 291 reviews

Happys Houseboat Key West

houseboat, Key West

Guest-Favourite Unique Stays with a Pool in Key West, FL

Dive into an on-site swimming pool whenever you fancy at these coastal unique stays in Key West, FL.

Wake Up On The Water | Luxury Marina | Key West - Key West, FL
10 10 reviews

Wake Up On The Water | Luxury Marina | Key West

boat, 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
3bedrm Sailboat Located In A Luxury Resort Village W All The Amenities Included - Key West, FL
No reviews

3bedrm Sailboat Located In A Luxury Resort Village W All The Amenities Included

houseboat, Stock Island
Oceanfront - Break Awai X Away Awai Floating Villas - Key West, FL
No reviews

Oceanfront - Break Awai X Away Awai Floating Villas

houseboat, Stock Island
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