Skip to main content

Holiday Rentals in Key West

Find the holiday rentals that appeal to you the most

The best holiday rentals in Key West

Check out our pick of great holiday rentals in Key West

Filter by:

Review score

L'Habitation Guesthouse- Adult Exclusive

Downtown Key West, Key West

Located in Key West, 600 metres from Key West Aquarium and 600 metres from Mallory Dock, L'Habitation Guesthouse- Adult Exclusive provides accommodation with free WiFi, air conditioning, a garden and...

P
Peter
From
Norway
Very nice staff and good communication. We came early to Key West, they sent us a message on booking as soon as our room was ready. There was a cute breakfast with nice options, we especially enjoyed the pastries and coffee from local vendors. The thing we were very surprised by, was the happy hour in the afternoon, when there was some vodka and cranberry out for us to enjoy. Well done!
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,417 reviews
Price from
US$219
1 night, 2 adults

Southernmost Point Guest House & Garden Bar

Downtown Key West, Key West

This Key West, Florida Southernmost Point Guest House & Garden Bar is located on Duval Street 110 metres from the Southernmost Point and 73 metres from the beach.

S
Silje Helene
From
Norway
Was not expecting much when I booked but I can't praise this place enough! The atmosphere, the rooms, the design, the location, the staff. It was just perfect from start to finish! Will be back!
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,180 reviews
Price from
US$481.85
1 night, 2 adults

Old Town Manor

Downtown Key West, Key West

This adult-only, pet friendly, smoke-free property is located in the heart of Key West less than 1.6 km from the Southernmost Point.

A
Ashanahan9
From
Canada
What a hidden gem! Clean and cozy. Air-conditioned. Amazing breakfast. Right in the heart of Key West. Recommended!
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,054 reviews
Price from
US$289
1 night, 2 adults

The Casablanca Hotel

Downtown Key West, Key West

Less than 2 minutes’ walk from the Ernest Hemingway Home and Museum, this historic Key West property features guest rooms with private balconies and free Wi-Fi.

S
Steve
From
Canada
The staff was very friendly and the room was very clean. The location was great as well. The bedding felt luxurious, and was a comfy sleep.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 520 reviews
Price from
US$135
1 night, 2 adults

Key West Villas

Downtown Key West, Key West

Located in the heart of historic Key West, guests will be 1 minutes’ walk from Duval Street. A heated pool, daily continental breakfast, and free WiFi are provided.

V
Viesturs
From
Latvia
everything, hosts are wonderful, we felt like old friends after first few hours spent there. location is great.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 340 reviews
Price from
US$979
1 night, 2 adults

The Artist House

Downtown Key West, Key West

This historical Key West bed and breakfast is 1 mile from the Southernmost Point and 3 minute’s walk from iconic Duval Street.

W
Werner Alberts
From
Isle of Man
The service of the staff is outstanding. They made us feel special and at home from the first minute. The house has a very interesting history and famous thrilling story but you need to hear it first hand. The rooms are large and very comfortable. All well airconditioned. The location is excellent and close to the main attractions. The breakfast are excellent with a wide selection. The selection of coffee is also excellent. Happy hour at 4pm is brilliant and the hosts are very generous with wine, beer , cake and other snacks. The splash pool was a life saver. The one day was 100+F and we spent 3 hours in the pool cooling down. It was such a social occasion with other guests.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 190 reviews
Price from
US$219.45
1 night, 2 adults

Evershore House -Pool, Parking, Dock!

Key West

Featuring air-conditioned accommodation with a private pool, Evershore House -Pool, Parking, Dock! is located in Key West.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews
Price from
US$1,526.05
1 night, 2 adults

The St Martin -Hot Tub & Pool

Key West

Boasting air-conditioned accommodation with a patio, The St Martin -Hot Tub & Pool is situated in Key West. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

g
gary
From
United Kingdom
Tennis court nearby and decent pool
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 16 reviews
Price from
US$244.95
1 night, 2 adults

The Exuma Cay -Pool View & Parking

Key West

Boasting air-conditioned accommodation with a patio, The Exuma Cay -Pool View & Parking is situated in Key West. Featuring a lift, this property also provides guests with an outdoor pool.

N
Nina
From
Netherlands
The apartment was spacious, clean and cozy. The beds, even the sofa bed, were comfortable. Two bathrooms with very nice showers. The kitchen was fully equipped with plenty of everything. This is very convenient for a family with food allergies since this actually allows for cooking your own safe meal. In our experience, this is exceptional; often times when kitchens are described as fully equipped, they are not. This was a nice exception. Excellent washer/drying combination. Nice pool, sufficient towels. Staff was very helpful: we requested extra dishwashing powder since we did our own cooking and it was brought over the next day. We had the most excellent stay!
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 33 reviews
Price from
US$285.20
1 night, 2 adults

Sky Loft in Key West

Downtown Key West, Key West

In the centre of Key West, located within a short distance of Simonton Street Beach and Duval Street, Sky Loft in Key West offers free WiFi, air conditioning and household amenities such as a...

P
Patrick
From
United Kingdom
Location, and general layout of the property.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 15 reviews
Price from
US$353.05
1 night, 2 adults
All holiday rentals in Key West

Most booked holiday rentals in Key West and surroundings in the past month

See all

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 769 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 1,155 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 520 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 864 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 317 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,054 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,417 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,180 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 658 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 1,765 reviews

Enjoy breakfast in Key West and nearby

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 811 reviews

Located centrally on lively Duval Street, Duval House offers a continental breakfast that includes Belgian waffles. The 7 Caribbean-style buildings offer free WiFi.

From US$325.13 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 189 reviews

Located above a nightclub on historic Duval Street in Key West, Florida, this gay male guest house features an outdoor swimming pool, a clothing-optional sundeck, and an on-site restaurant.

From US$248.92 per night
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 30 reviews

This adult-only Conch House Heritage Inn offers accommodation in Key West with breakfast included and complimentary mimosas.

From US$307.80 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 1,279 reviews

Offering an outdoor pool, this historic Key West property is just 1 minutes’ walk from Duval Street. Free WiFi and a light continental breakfast are provided daily to all guests.

From US$336.38 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 401 reviews

Featuring free WiFi throughout this adult-only property, Caribbean House offers accommodation in Key West.

From US$363.04 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 658 reviews

Set in Key West, less than 1 km from South Beach, La Pensione Inn - Adult Exclusive offers accommodation with an outdoor swimming pool, free private parking, a shared lounge and a terrace.

From US$246.38 per night
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 859 reviews

This all-adult bed and breakfast is within a 10-minute walk of Duval Street and the Atlantic Ocean.

From US$404.22 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 317 reviews

Key West Bed and Breakfast, a property with a garden, is situated in Key West, 1.2 km from Key West Aquarium, 1.3 km from Ernest Hemingway Home and Museum, as well as 1.1 km from Mallory Dock.

From US$213.75 per night

These holiday rentals in Key West and nearby have options with free cancellation

Road's End

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 17 reviews

Located within the Downtown Key West district in Key West, Road's End has air conditioning, a patio, and city views.

Scored out of 10, guest rating 7.5
Good - What previous guests thought, 17 reviews

Right in the heart of Key West, situated within a short distance of South Beach and Ernest Hemingway Home and Museum, Casa Key West-Pool & Free Parking offers free WiFi, air conditioning and household...

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 14 reviews

Located in the centre of Key West, 600 metres from South Beach and 500 metres from Ernest Hemingway Home and Museum, New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool offers free WiFi and...

From US$946.52 per night
Scored out of 10, guest rating 5.0
Passable - What previous guests thought, 2 reviews

Set in the centre of Key West, 600 metres from South Beach and 500 metres from Ernest Hemingway Home and Museum, NEW!

From US$1,046.14 per night
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 26 reviews

In the heart of Key West, set within a short distance of South Beach and Ernest Hemingway Home and Museum, Sea Breeze -Great Location!

From US$695.31 per night
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Located in the centre of Key West, less than 1 km from South Beach and a 3-minute walk from Duval Street, Contra House -Luxury Home With Pool offers free WiFi, a garden and air conditioning.

From US$1,798.71 per night

Keys Please!

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 7 reviews

Set in the centre of Key West, 300 metres from South Beach and 400 metres from Southernmost Point, Keys Please! offers free WiFi, a garden and air conditioning.

The Collins on Duval

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 6.4
Pleasant - What previous guests thought, 6 reviews

In the heart of Key West, set within a short distance of Simonton Street Beach and Duval Street, The Collins on Duval offers free WiFi, air conditioning and household amenities such as a fridge and...

From US$899.72 per night

Highly rated holiday rentals in Key West and nearby

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 472 reviews

Located in Key West, Florida, these furnished self-catering apartments feature free WiFi access. The Ernest Hemingway Home and Museum is only 3 minutes’ walk away from Old Town Suites.

From US$409.74 per night
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 27 reviews

Boasting air-conditioned accommodation with a patio, Hemingway's View is situated in Key West. Located in the Downtown Key West district, the property provides guests with access to a hot tub.

From US$765.90 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 25 reviews

Boasting air-conditioned accommodation with a patio, Amelia House is situated in Key West.

From US$631.35 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 864 reviews

Alexander Palms Court - No Hidden Resort Fees! provides accommodation located less than 1 km from the centre of Key West and features an outdoor swimming pool and a garden.

From US$403.88 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 260 reviews

Set within 500 metres of Key West Aquarium, Weatherstation Inn Circa 1911 is an adult-only bed and breakfast in Key West and features a number of amenities including an outdoor swimming pool and a...

From US$246.38 per night
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 301 reviews

Located in Key West, Florida, these villas feature a heated outdoor swimming pool. They are adjacent to dining and shopping on Duval Street. and 1.8 km from the Southernmost Point.

From US$325.13 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 349 reviews

Well located in Key West, The Garden House provides express check-in and check-out and private parking.

From US$232.88 per night
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 24 reviews

Ideally situated in the centre of Key West, Creme Brulee Suite features air-conditioned rooms, a garden and free WiFi.

From US$402.92 per night

Holiday Rentals with swimming pools in Key West and nearby

Scored out of 10, guest rating 7.7
Good - What previous guests thought, 122 reviews

Centrally located in Key West's Old Town, this intimate Florida inn offers bright, tropical rooms. It is 4 blocks from the beach and 2 blocks to dining on Duval Street.

From US$336.38 per night
Scored out of 10, guest rating 7.0
Good - What previous guests thought, 7 reviews

Situated in the centre of Key West, 1 km from Simonton Street Beach and 800 metres from Duval Street, Curry House Room 6 offers free WiFi, a garden and air conditioning.

From US$478.91 per night

Set in the centre of Key West, 1 km from Simonton Street Beach and 800 metres from Duval Street, Curry House - Room 2 offers free WiFi, a garden and air conditioning.

From US$427.05 per night
Scored out of 10, guest rating 6.4
Pleasant - What previous guests thought, 7 reviews

Situated in the centre of Key West, 1 km from Simonton Street Beach, Curry House - Room 1 features air-conditioned rooms and free WiFi.

From US$445.16 per night
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 4 reviews

Located in the centre of Key West, 700 metres from Higgs Beach and 1 km from Southernmost Point, Sunnyside Up offers free WiFi, a garden and air conditioning.

From US$991.86 per night
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 1,765 reviews

This bed and breakfast welcomes guests to Old Town, Key West and boasts a free continental breakfast, 3 outdoor pools and a hot tub. The Ernest Hemingway Home and Museum is 15 minutes’ walk away.

From US$175.60 per night
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 3 reviews

Situated within the Downtown Key West district in Key West, Banana Split has air conditioning, a patio, and city views.

From US$454.73 per night
Scored out of 10, guest rating 3.5
Poor - What previous guests thought, 2 reviews

Ideally set in Key West, Sugar Pie Suite offers air-conditioned rooms, a garden and free WiFi.

From US$377.04 per night

FAQ about holiday rentals in Key West

Holiday rentals that guests love in Key West

See all
Avg. price/night: US$325.13
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 301 reviews
best location!! plenty of space for the family!! i will surely come back and stay the villas!!
Guest review by
Ailen
Family with young children
Avg. price/night: US$336.38
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 340 reviews
Everything was wonderful. The villas had everything you needed to make your trip enjoyable. Looking forward to going back again soon.
Guest review by
erica
Group
Avg. price/night: US$336.38
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 340 reviews
Perfect location, but even more importantly, Heather and Kevin were dream hosts. The snacks, cocktails and customer service were outstanding. I would recommend Key West villas to everyone!
Guest review by
Thomas
Group
Avg. price/night: US$325.13
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 301 reviews
Absolutely beautiful great sized villa. Comfortable, convenient location, staff was excellent and villa was spotless. Parking and pet friendly with a nice pool - all excellent bonuses! So nice that when I walked in I immediately called the office and extended my stay by two nights!
Guest review by
lisa
Solo traveller