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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

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 8.7
Fabulous - What previous guests thought, 706 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,407 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 519 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 321 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 9.0
Superb - What previous guests thought, 766 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,167 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,048 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 1,746 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 656 reviews

Highly rated holiday rentals in Key West and nearby

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 470 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$338.63 per night
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.

From US$743.18 per night
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$1,210.44 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 27 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$833.74 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 190 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$308.19 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 393 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, 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$358.88 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 321 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$329.65 per night

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

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$1,297.13 per night

Coconut Palm

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 5.5
Passable - What previous guests thought, 2 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...

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.

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$1,131.42 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$1,049.92 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$557.83 per night

Curry House - Room 2

Downtown Key West, Key West
Free cancellation options available

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$521.49 per night

Curry House - Room 1

Downtown Key West, Key West
Free cancellation options available
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$539.61 per night

Enjoy breakfast in Key West and nearby

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 1,746 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

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$1,258.82 per night
Scored out of 10, guest rating 8.1
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 9.5
Exceptional - What previous guests thought, 153 reviews

Located right off Duval Street, the Andrews Inn and Garden Cottages are less than 5 minutes’ walk from various dining and entertainment options. Guests can enjoy free WiFi and an outdoor pool.

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 9 reviews

Featuring air-conditioned accommodation with a balcony, Crawl to Duval w/ Hot tub is located in Key West. This property offers access to a terrace and free private parking.

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 16 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...

From US$1,516.67 per night

Holiday Rentals with swimming pools in Key West and nearby

In the heart of Key West, set within a short distance of South Beach and Ernest Hemingway Home and Museum, Southern Palms offers free WiFi, air conditioning and household amenities such as a microwave...

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 259 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$223.88 per night
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 299 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$403.88 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.

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$446.91 per night
Scored out of 10, guest rating 7.0
Good - What previous guests thought, 2 reviews

In a prime location in the centre of Key West, Key Lime Cottage offers air-conditioned rooms, a garden and free WiFi.

From US$481.84 per night
Scored out of 10, guest rating 7.0
Good - What previous guests thought, 1 review

Well situated in Key West, Honey Bun Hideaway offers air-conditioned rooms, a garden and free WiFi. The property is close to Mallory Square, Duval Street and Ernest Hemingway Home and Museum.

From US$475.37 per night
Scored out of 10, guest rating 7.9
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$477.96 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$403.88
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 299 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
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 336 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
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 336 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$403.88
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 299 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
gogless