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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

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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...

S
Shelly
From
Israel
Beautiful house, great hosts, very clean room and a comfy bed. Close to the nain street yet quiet. Delicious breakfast.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,412 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.

А
Александър К..
From
Bulgaria
The house has a great location and it is on walkable distance of the restaurants and shops. Staff was so polite and the room was pretty awesome. You can feel the Key West atmosphere in this guest house. Definitely we will visit it again.
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
Andrea
From
Hungary
It way absolutely amazing. The room was very nice and clean, it had an antique vibe. The bed was very comfortable and big. The breakfast was the best part, with very delicious choices.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,052 reviews
Price from
US$289
1 night, 2 adults

Weatherstation Inn Circa 1911

Downtown Key West, Key West

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...

G
Gerrit-Jan
From
Netherlands
Quiet location, gated community. Close to Mallory Square en Duval. Spacious rooms, excellent beds.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 258 reviews
Price from
US$199
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.

T
Thomas
From
Germany
Very nice and courteous staff.trying all for the guest to have a comfortable stay there. Perfect location. See you definitly again.thank you. Greetings from Germany
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 523 reviews
Price from
US$145
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.

M
Marek Andrzej
From
Poland
great location, nice service ,
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.

K
Kaicheng
From
United States
Great breakfast, beautiful room decor, perfect location
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 188 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$1,460.50
1 night, 2 adults

Keys Please!

Downtown Key West, Key West

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.

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 6 reviews
Price from
US$770.50
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
All holiday rentals in Key West

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

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Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 812 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 1,160 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 523 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,052 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 657 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 863 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 316 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 9.1
Superb - What previous guests thought, 1,412 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 1,766 reviews

Holiday Rentals with swimming pools in Key West and nearby

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$981.45 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$1,081.07 per night
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Set in Key West, 300 metres from Duval Street and 200 metres from Ernest Hemingway Home and Museum, Duval Street Suite w kitchen and shared heated pool offers a garden and air conditioning.

From US$255.10 per night
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 4 reviews

Set in the centre of Key West, 700 metres from South Beach and 300 metres from Duval Street, Duval Street Suite overlooking Duval w parking and pool offers free WiFi, a garden and air conditioning.

Scored out of 10, guest rating 5.3
Passable - What previous guests thought, 3 reviews

Right in the heart of Key West, situated within a short distance of South Beach and Ernest Hemingway Home and Museum, Coconut Palm offers free WiFi, air conditioning and household amenities such as a...

From US$1,210.61 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 1,275 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

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

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$719.89 per night

Traveler's Palm

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 7.8
Good - What previous guests thought, 45 reviews

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

From US$484.37 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 657 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

Sky Loft in Key West

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 15 reviews

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...

From US$559.46 per night

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

<h2>Spacious Accommodation</h2> The Collins on Duval in Key West offers a spacious apartment with two bedrooms and a living room.

From US$935.81 per night

Duval Dream Loft on Duval

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 7.1
Good - What previous guests thought, 26 reviews

Situated in the centre of Key West, less than 1 km from Simonton Street Beach and a 3-minute walk from Duval Street, Duval Dream Loft on Duval offers free WiFi and air conditioning.

From US$884.58 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 863 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

Curry House Room 6

Downtown Key West, Key West
Free cancellation options available
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$495.73 per night

Enjoy breakfast in Key West and nearby

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 316 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
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 1,766 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 8.8
Fabulous - What previous guests thought, 733 reviews

Within walking distance of the beach, local attractions and activities, this Old Town Key West inn features on-site laundry facilities, comfortable guest rooms and an extended continental breakfast.

From US$292.50 per night

Paradise Suite has a patio and is situated in Key West, within just 400 metres of Duval Street and 300 metres of Ernest Hemingway Home and Museum.

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 8.2
Very good - What previous guests thought, 13 reviews

Situated in the centre of Key West, 700 metres from South Beach and 200 metres from Ernest Hemingway Home and Museum, Just steps to Duval- Sleeps 10- Heated Pool House offers free WiFi, a garden and...

Set in the centre of Key West, 700 metres from South Beach and 200 metres from Ernest Hemingway Home and Museum, BachelorPARTY HQ for 16-Feet to Duval-Pool-Hot tub offers free WiFi, a garden and air...

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 523 reviews

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.

From US$275.63 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.

Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 300 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 8.0
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$417.15 per night
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 12 reviews

Right in the heart of Key West, situated within a short distance of Simonton Street Beach and Key West Aquarium, Mesa House, Dos -Unreal Location offers free WiFi, air conditioning and household...

From US$866.48 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 9 reviews

Attractively situated in Key West, Classic King Balcony at the James House features air-conditioned rooms, a garden and free WiFi.

From US$308.34 per night
Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 41 reviews

Ideally set in the centre of Key West, King Suite at Curry Mansion with Heated Pool! features free WiFi throughout the property and a garden.

From US$314.98 per night
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 57 reviews

Boasting air-conditioned accommodation with a balcony, Atlantic Ocean View is located in Key West. Featuring a lift, this property also has a restaurant and an outdoor pool.

From US$633.32 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 22 reviews

Located in Key West in the Florida region, Sunrise Suites Big Kahuna Suite #202 has a balcony. Guests can benefit from a terrace and an outdoor pool. The apartment features a hot tub and a lift.

From US$694.74 per night

FAQ about holiday rentals in Key West

Holiday rentals that guests love in Key West

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Avg. price/night: US$325.13
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 300 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$392.63
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$392.63
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, 300 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