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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...

t
tracey
From
United Kingdom
fabulous location in the middle of everything. but stil quiet . our room was big comfy and spotless. the maids were superb every day. staff si friendly
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,413 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.

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

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.

M
Masha
From
Czech Republic
The staff were great, welcoming and informative. Comfortable room and bathroom, though small. We especially enjoyed the breakfast in the beautiful back garden, with waffles, toast and much more.
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

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...

M
Michele
From
United States
Location location this was great you were a block maybe two away from Sloppy Joe's and Deval Street close to Mallory Square you are off the beaten path but close to everything I would recommend this it was wonderful I felt safe staying there after hours they lock the gate so you had a key to get in but I could walk back to my room feeling safe it was a wonderful place to stay the staff was wonderful this will be my new place every time I come to the Keys now which is once a year
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

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.

N
Nadia
From
Austria
we loved it, very beautiful room, staff extremely helpful and accommodating, location is beautiful, pool is lovely!! highly recommend!!
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

Key West (Near 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

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.

D
Dearbhla
From
Ireland
One word - WOW!! Absolutely loved our stay here and will be back! The rooms are massive for Key West with charming decor. Staff are incredible, so friendly and helpful. Fantastic complementary breakfast in the gorgeous garden. Can’t recommend this place highly enough!
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 (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$1,521.45
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$769.35
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$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 7.4
Good - What previous guests thought, 1,766 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, 864 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 8.8
Fabulous - What previous guests thought, 1,159 reviews

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, 1,277 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 8.6
Fabulous - What previous guests thought, 860 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

Enjoy breakfast in Key West and nearby

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 860 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, 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$212.63 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 1,159 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$156.38 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, 1,277 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 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 8.9
Fabulous - What previous guests thought, 812 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 9.3
Superb - What previous guests thought, 1,180 reviews

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.

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$1,021.61 per night
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 91 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$310.46 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 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 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$968.51 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$1,066.84 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.

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

Keys Please!

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 6 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 Casablanca Hotel

Downtown Key West, Key West
Free cancellation options available
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$219.38 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$490.56 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$437.40 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$456.81 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$710.83 per night

Sky Suite On Duval

Downtown Key West, Key West
Free cancellation options available
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 8 reviews

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

From US$851.46 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$1,193.79 per night

Highly rated holiday rentals in Key West and nearby

Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 26 reviews

Leeward Isle has a patio and is located 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, 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 8.7
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 8.1
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 9.7
Exceptional - What previous guests thought, 340 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$392.63 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, 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 9.0
Superb - What previous guests thought, 767 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$358.88 per night