Compare unique places in Key West, FL from 100+ sites!

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

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Key West, FL unique stays
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

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.

Docked In Paradise - Key West, FL
9.0 7 reviews

Docked In Paradise

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.
Dolce Vita - Key West, FL
No reviews

Dolce Vita

boat, Stock Island
Dole Vita, a boat accommodation, is located near Key West International Airport, 2.5 miles away, offering convenient access to Stock Island attractions.
This family-friendly vessel accommodates up to 7 guests with 2 bedrooms and 2 bathrooms, featuring air conditioning, a private swimming pool, a terrace, free WiFi, and on-site parking.
Ocean Views! <Br>i Didnt Do It Too - Key West, FL
9.8 32 reviews

Ocean Views! <Br>i Didnt Do It Too

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.
Beautiful Houseboat In Key West - Key West, FL
9.9 230 reviews

Beautiful Houseboat In Key West

barge, Stock Island
This barge is located in Stock Island, just a short distance from Key West's historic district and the Southernmost Point of the Continental US. The surrounding area is peaceful and offers a tranquil escape from the bustle of Key West. This barge has received excellent ratings for its cleanliness, location, and overall user experience.
The barge has two bedrooms and one bathroom, comfortably accommodating up to four guests. The barge offers a kitchen with a fridge, freezer, and microwave, air conditioning, a garden, parking, and internet access, as well as a shuttle service for convenient travel to nearby attractions.

Best Key West, FL unique accommodations with a garden

*August/september Specials* Off Grid Boat Key West - Key West, FL
9.9 89 reviews

*August/september Specials* Off Grid Boat Key West

boat, Key West
The Shanty Pineapple houseboat, a unique Key West floating accommodation, is moored in Key West's bay and accessible only by water taxi or private boat.
This adult-oriented vessel offers a one-bathroom, three-guest capacity, featuring a basic kitchenette, outdoor shower, a clear kayak, and a DVD player; discounted overnight rates are available with the Salty Sandbars Key West private sandbar boat charter.
Southern Bell Is A Beautiful Houseboat Cozy And Relaxing. - Key West, FL
10 9 reviews

Southern Bell Is A Beautiful Houseboat Cozy And Relaxing.

houseboat, Stock Island
This Key West houseboat is situated near Stock Island, within one mile of Robbie's Marina (famous for its tarpon feeding) and the Key West Tropical Forest & Botanical Garden, and within two miles of the Stock Island Yacht Club & Marina.
This luxurious vessel offers four bedrooms, two bathrooms, sleeps eight guests, and boasts a kitchen, air conditioning, internet access, and a terrace—all within a smoke-free environment.
The Grand Tiki At Tiki Suites  A Floating Oasis In Key West - Key West, FL
10 1 review

The Grand Tiki At Tiki Suites A Floating Oasis In Key West

houseboat, Key West
This unique floating retreat is anchored in shallow waters off Key West's Meadows district, offering a secluded experience with proximity to attractions like the Ernest Hemingway Home and Museum and Southernmost Point.
This houseboat accommodates two guests with one bedroom and one bathroom, featuring air conditioning, an artistic roof, Ipe hardwood decking, and included recreational equipment like paddleboards and snorkel gear for exploring the nearby waters.
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.

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.
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.
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 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.
Windward Isle - Key West, FL
8.9 485 reviews

Windward Isle

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.

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 - Key West, FL
8.9 7 reviews

Dream Catamaran

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.
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 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.
Classic Boat Sleeps Up To 8 People - Key West, FL
9.7 6 reviews

Classic Boat Sleeps Up To 8 People

barge, Stock Island
This unique houseboat, named the "Romantic Trawler," offers a prime marina location in Key West, just a short shuttle ride from downtown attractions.
This accommodation sleeps up to 8 guests with 2 bedrooms and 2 bathrooms, featuring air conditioning, a microwave, internet, and access to marina amenities including two swimming pools and a fitness center.
Elegant Sailboat Stay - Key West, FL
No reviews

Elegant Sailboat Stay

boat, Stock Island
This Stock Island sailboat rental, located five miles from the Ernest Hemingway Home and Museum, offers a tranquil escape near Key West's attractions.
The 360-square-foot vessel features two bedrooms, one bathroom with a hot tub, a full kitchen, and accommodates up to seven guests, complete with amenities like a private patio, free Wi-Fi, and a free shuttle to Key West's historic district.

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.

The Easy Way  Comfy, Practical, Convenient - Key West, FL
10 24 reviews

The Easy Way Comfy, Practical, Convenient

boat, Key West

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.

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

Oceanfront - Break Awai X Away Awai Floating Villas

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
Resort Chic On The Water! - Key West, FL
9.4 20 reviews

Resort Chic On The Water!

boat, Stock Island
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
©2026 cozycozy.com