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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

Key West (Near 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...

L
Lisandre
From
Canada
Awesome stay! We were welcomed by Foster who gave us great recommandations and was really friendly! The location was perfect!
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,422 reviews
Price from
US$219
1 night, 2 adults

Southernmost Point Guest House & Garden Bar

Key West (Near 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.

E
Elaine
From
Falkland Islands (Malvinas)
The room was spectacular and breakfast was delicious
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,176 reviews
Price from
US$481.85
1 night, 2 adults

Old Town Manor

Key West (Near 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.

S
Sue
From
Ireland
I personally really liked the staff. They genuinely couldn’t do enough for us. The girl serving breakfast was so good to each and everyone of us. Rachel at the front desk was so welcoming to us and not to mention the handsome cat Doc 😻Thank you to you all for making a wonderful Christmas for me and my family .
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,059 reviews
Price from
US$289
1 night, 2 adults

Grand Marina Suite -Waterfront Condo

Key West (Near Key West)

Located in Key West, 9.1 km from Ernest Hemingway Home and Museum and 9.2 km from Duval Street, Grand Marina Suite -Waterfront Condo offers a garden and air conditioning.

p
pawel
From
Poland
Great, spacious, 3bath apartment. Everything anyone could wish for.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 124 reviews
Price from
US$422.28
1 night, 2 adults

Weatherstation Inn Circa 1911

Key West (Near 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...

A
Alon
From
Israel
highly recommend. This is not a hotel in the full sense of the word. But this is a great bed and breakfast. Well maintained, in a very quiet, semi-private neighborhood. Walking distance from everything and there is also parking. A large shower with plenty of towels and other things.
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 258 reviews
Price from
US$199
1 night, 2 adults

The Casablanca Hotel

Key West (Near 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.

A
Andrew
From
United Kingdom
Super cute little hotel right in the heart of Duval street, but far enough from the Mallory Square end that it's not totally crazy outside. Tons of great restaurants and bars within a few blocks. Nice little pool and adjoining bar. Our room had a large deck with chairs that faced into some palm trees at the edge of the property. Really nice spot to read in the morning or just chill whenever.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 523 reviews
Price from
US$145
1 night, 2 adults

The Artist House

Key West (Near 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, 187 reviews
Price from
US$219.45
1 night, 2 adults

Evershore House -Pool, Parking, Dock!

Key West (Near 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$918.85
1 night, 2 adults

Keys Please!

Key West (Near 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 (Near 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$269.10
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 7.4
Good - What previous guests thought, 1,765 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 862 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 522 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 8.8
Fabulous - What previous guests thought, 659 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 813 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 1,272 reviews

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 859 reviews

Popular with guests booking holiday rentals in Key West

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

Popular with guests booking holiday rentals in Key West

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 368 reviews

Highly rated holiday rentals in Key West and nearby

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$477.97 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 659 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$291.38 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 1,160 reviews

Featuring free WiFi, a sun terrace with a swimming pool and a garden, Authors Key West Guesthouse is situated in Key West. It is set 1.7 km from South Beach and features a concierge service.

From US$190.13 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 862 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 9.2
Superb - What previous guests thought, 31 reviews

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

From US$429.30 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 1,272 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$325.13 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.

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$430.05 per night

Holiday Rentals with swimming pools in Key West and nearby

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$1,145.81 per night
Scored out of 10, guest rating 7.2
Good - What previous guests thought, 90 reviews

Located in Key West, this Florida hotel is 1.6 km from the shopping, entertainment, and nightlife of Duval Street. Features include a shared outdoor pool with a waterfall and free property-wide WiFi.

From US$291.38 per night
Scored out of 10, guest rating 6.1
Pleasant - What previous guests thought, 34 reviews

This boutique hotel offers a landscaped tropical garden and a lagoon-style dipping pool. It is located in the Casa Marina Area of Key West, Florida, only 3 blocks from the beach.

From US$264.77 per night
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$291.38 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$1,137.99 per night
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...

From US$1,483.03 per night
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 522 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$309.38 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$614.76 per night

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

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$480.09 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$502.09 per night

Nyah - Adult Exclusive

Downtown Key West, Key West
Free cancellation options available
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$236.35 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$616.39 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$801.39 per night

Cloud Suite On Duval

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 13 reviews

Situated in the centre of Key West, less than 1 km from South Beach and a 1-minute walk from Duval Street, Cloud Suite On Duval offers free WiFi and air conditioning.

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 39 reviews

In a central area of Key West, set within a short distance of Simonton Street Beach and Duval Street, The Island Suite at KW Vacation offers free WiFi, air conditioning and household amenities such as...

From US$463.73 per night

Coconut Palm

Downtown Key West, Key West
Free cancellation options available
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$1,402.09 per night

Enjoy breakfast in Key West and nearby

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 813 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 9.7
Exceptional - What previous guests thought, 342 reviews

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.

From US$448.88 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 8.8
Fabulous - What previous guests thought, 738 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$258.75 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 315 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$201.38 per night
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 769 reviews

This Key West bed and breakfast is 3 minutes’ walk from the art galleries and cafés of historic Duval Street. Guests can start their day with a full hot breakfast and enjoy two outdoor pools.

From US$392.63 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 353 reviews

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

From US$277.88 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 402 reviews

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

From US$363.04 per night