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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...

J
Jeffrey
From
United States
The Concierge (Foster) who checked us in, out and everything in between was truly exceptional. We felt at home thanks to Foster. The rest of the staff were also very friendly and always smiling. The room's television was larger than most hotels and is a perfect fit for the room. We shared a deck, under the trees, with our neighboring room. Our doorway onto the deck was our only doorway and was a French door. This was a nice touch for a romantic birthday get-a-way. The room was very nice and the mattress and pillows were extremely comfortable.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,420 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.

C
Claire
From
Bermuda
So beautiful, out room was comfortable, big and the location can’t be beaten.
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

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.

T
Tomáš
From
Slovakia
Helpful employees, pleasant furniture equipment, exceptional breakfast.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 1,057 reviews
Price from
US$289
1 night, 2 adults

Grand Marina Suite -Waterfront Condo

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.

K
Kim
From
United States
Large room for a family, has everything you need. Lovely place with a wonderful pool with a beautiful view.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 124 reviews
Price from
US$420.21
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.

W
William
From
United States
Amazing hotel. Met all my expectations.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 524 reviews
Price from
US$145
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.

S
Sophie
From
United Kingdom
Everything was fantastic! A very quirky guesthouse. The turret suite was perfect for a family of 4 and the balcony was an added bonus. The complementary breakfast was lovely and the happy hour is a great idea, giving chance to chat to other guests. Jess and Shaun were really hospitable and couldn’t really have done any more.
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

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!

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$757.85
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$266.80
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$318.55
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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Highly rated holiday rentals in Key West and nearby

  • Scored out of 10, guest rating 8.1
    Very good - What previous guests thought, 473 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$685.15 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$1,802.98 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!

  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 816 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$448.88 per night
  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 188 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$388.80 per night
  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 1,274 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$426.38 per night
  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 404 reviews

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

    From US$392.29 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$1,720.18 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...

  • 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$992.81 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 8.8
    Fabulous - What previous guests thought, 865 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$235.13 per night
  • The Grand Guesthouse

    Downtown Key West, Key West
    Free cancellation options available
    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
  • 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$820.46 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$711.68 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 7.7
    Good - What previous guests thought, 123 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$313.88 per night
  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 77 reviews

    Offering a year-round outdoor pool and terrace, this adult-only (21 years +) Marreros Guest Mansion is set in the Duval district in Key West. Duval Street is a 1 minute walk from the property.

    From US$572.63 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$714.26 per night
  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 258 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$505.13 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$415.13 per night
  • Scored out of 10, guest rating 7.4
    Good - What previous guests thought, 1,768 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$308.60 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$809.16 per night

Enjoy breakfast in Key West and nearby

  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 312 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$302.63 per night
  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 355 reviews

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

  • Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 743 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$388.13 per night
  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 1,163 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$167.63 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 7.9
    Good - What previous guests thought, 25 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.

  • 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...

FAQ about holiday rentals in Key West

Holiday rentals that guests love in Key West

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  • Avg. price/night: US$415.13
    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, 346 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, 346 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$415.13
    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