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The best holiday rentals in Key West

Check out our pick of great holiday rentals in Key West

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Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
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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. Features include a free hot American breakfast and a hot tub.The property is located across 4 buildings.

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

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9.2
Superb
1,151 reviews
Price from
£192
per night

The Speakeasy Inn and Rum Bar features accommodation within 400 metres of the centre of Key West, with free WiFi, and a kitchenette with a microwave, a fridge and kitchenware. This bed and breakfast provides free private parking and luggage storage space. Guests can access the bed and breakfast via private entrance.

This place was amazing for our first time to KW. Clean and comfortable and the room was really nice. We had fun hanging in the rum bar downstairs which is low key and closes at 11pm so we didn't find noise to be an issue at all. Would choose it again.

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9.1
Superb
179 reviews
Price from
£188
per night

Situated in the centre of Key West, 600 metres from Simonton Street Beach, the historic Key West Harbor Inn - Adults Only features accommodation with free WiFi and an indoor pool. The property features pool and garden views, and is 1.8 km from South Beach. The bed and breakfast has facilities for disabled guests.

What a beautiful quiet little Oasis in the middle of chaos. We absolutely loved this place and all the staff. I was such a pleasant surprise it was. We booked the same room for next October before we checked out.

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9.3
Superb
427 reviews
Price from
£195
per night

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.

Each room at this bed and breakfast is air conditioned and comes with a flat-screen TV. Some units have a seating area where you can relax.

This was a super cute property with unique rooms and decor. The pool access was very valuable! And the staff was super friendly and accommodating!

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9.4
Superb
136 reviews
Price from
£238
per night

Featuring garden views and a garden, Key West Bed and Breakfast features accommodation attractively located in Key West, within a short distance of Fort Zachary Taylor State Park Beach, Duval Street and Mallory Square. The air-conditioned accommodation is 1.7 km from South Beach. The property is 700 metres from the city centre and 1.1 km from Simonton Street Beach.

breakfast was good, the use of the pool next door and how quiet it was

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9.3
Superb
236 reviews
Price from
£177
per night

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. Guests will enjoy a daily breakfast including pastries, organic fruit, and dessert cakes during their stay.

Such a beautiful and magical historic manor in the center of Key West. and they have a house cat!

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9
Superb
965 reviews
Price from
£158
per night

All rooms feature a private bath, small refrigerator, and microwave. Apartments at Key West Villas include a fully-equipped kitchen and seating area.

Key West Villas guests can hire a bicycle and explore Key West. A guest launderette is available as well.

Friendly staff and complimentary breakfast

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9.7
Exceptional
352 reviews
Price from
£220
per night

This historical Key West bed and breakfast is 1 mile from the Southernmost Point and 3 minute’s walk from iconic Duval Street. The Artist House guests will enjoy a daily continental breakfast and spa hot tub.

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.

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9.1
Superb
143 reviews
Price from
£253
per night

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.

A flat-screen TV and an iPod docking station are featured in each classic room at this Key West bed and breakfast. Guests will also enjoy the convenience of a refrigerator in their room. Rooms also have a clock radio with auxiliary cables.

The inn is beautiful, perfectly located, excellent amenities and benefits (breakfast, happy hours, pool), the room was cute and nothing was missing, and Isabella is the nicest person you could meet in Key West. Thank you!

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9.4
Superb
109 reviews
Price from
£249
per night

This all-adult bed and breakfast is within a 10-minute walk of Duval Street and the Atlantic Ocean. This environmentally-friendly inn offers in-room refrigerators, bicycle rentals and a continental breakfast.

The continental breakfast was excellent and loved being able to eat outside in the beautiful yard space. The location was within an easy walk to the main tourist areas and was very safe. Our room had everything we needed and we loved being able to sit in the two chairs outside the door.

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9.2
Superb
677 reviews
Price from
£147
per night

Most booked holiday rentals in Key West this month

Enjoy breakfast in Key West!

  • Southernmost Point Guest House & Garden Bar
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 1,151 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.

    The room was spectacular and breakfast was delicious

  • Marreros Guest Mansion - Adult Only
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 136 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.

    staff was very friendly!! Location was fantastic!!

  • Old Town Manor
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 965 reviews

    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.

    Climate place :) Great breakfast in the garden :)

  • The Grand Guesthouse
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 677 reviews

    This all-adult bed and breakfast is within a 10-minute walk of Duval Street and the Atlantic Ocean.

    Great staff, super clean rooms, excellent location

  • The Conch House Heritage Inn
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 38 reviews

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

    Breakfast was wonderful - presentation was lovely.

  • L'Habitation Guesthouse- Adult Exclusive
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 1,379 reviews

    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...

    Really nice place, confortable room, amazing staff.

  • Authors Key West Guesthouse
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 1,269 reviews

    Featuring free WiFi, a sun terrace with a swimming pool and a garden, Authors Key West Guesthouse is situated in Key West.

    Really big room, nice and clean. A decent breakfast.

  • Courtney's Place Historic Cottages & Inns
    8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 1,420 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.

    Everything. We've stayed at Courtney's several times.

These holiday rentals in Key West have options with FREE cancellation

  • Key West Harbor Inn - Adults Only
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 427 reviews

    Situated in the centre of Key West, 600 metres from Simonton Street Beach, the historic Key West Harbor Inn - Adults Only features accommodation with free WiFi and an indoor pool.

    very nice and beautiful place with a perfect location

  • Sky Loft in Key West by Brightwild
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 8 reviews

    In the centre of Key West, located within a short distance of Simonton Street Beach and South Beach, Sky Loft in Key West by Brightwild offers free WiFi, air conditioning and household amenities such...

    Great location. Very quiet and private but still close to Duval St. Blackout shades in bedroom made for excellent sleeping.

  • The Andros by Brightwild-4th Floor Sunset View
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 32 reviews

    Featuring air-conditioned accommodation with a patio, The Andros by Brightwild-4th Floor Sunset View is located in Key West.

    Très spacieux et très propre, très bon rapport qualité / prix

  • Alexander Palms Court - No Hidden Resort Fees!
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 903 reviews

    Well located in Key West, Alexander Palms Court - No Hidden Resort Fees! provides express check-in and check-out and parking on-site.

    Great location, very nice, close to everything by foot

  • Weatherstation Inn Circa 1911
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 226 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...

    The location is perfect. It's close to everything!!!

  • Rose Lane Villas
    Free cancellation options available
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 268 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.

    clean. well equipped and the location was amazing.

  • The Casablanca Hotel
    Free cancellation options available
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 560 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.

    The location is perfect! Staff is very friendly too

  • La Pensione Inn - Adult Exclusive
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 595 reviews

    Located in Key West, this ages 21 and older adult-only Florida bed and breakfast features an outdoor swimming pool and a daily continental breakfast.

    It is really nice and cozy and good neighbourhood.

Highly rated holiday rentals in Key West

  • Studio Blue
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 5 reviews

    Right in the heart of Key West, situated within a short distance of Rest Beach and Higgs Beach, Studio Blue offers free WiFi, air conditioning and household amenities such as an oven and coffee...

  • Seaport Inn
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 323 reviews

    Located in the heart of the historic Seaport District in Old Town, Seaport Inn features an outdoor pool and barbecue and is 600 metres' walk from Mallory Dock.

    Nice location and good impression of Key West Living

  • The Garden House
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 389 reviews

    Located in the heart of Old Town Key West, Garden House features an outdoor pool and 2nd-level sun deck. Guests can also enjoy free WiFi and a continental breakfast.

    The staff is very friendly, and is a beautiful place

  • Old Town Suites
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 401 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.

    Location, size of the apartment, separate bedrooms

  • New Orleans House - Gay Male Adult Guesthouse
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 282 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.

    Everything was awesome but had to pay for parking.

  • Duval House
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 859 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.

    the quirkyness of the cottage and beautiful gardens

  • King Suite Balcony by Brightwild- at James House
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 22 reviews

    Set within the Downtown Key West district in Key West, King Suite Balcony by Brightwild- at James House has air conditioning, a patio, and city views.

    חדר נעים מיקום מצויין קרוב למקומות העניין המרכזיים בקיי וסט.

  • Deluxe King with Balcony by Brightwild- at James House with Parking!
    8.1
    Scored 8.1
    Very good
    Rated very good
     · 9 reviews

    Situated within the Downtown Key West district in Key West, Deluxe King with Balcony by Brightwild- at James House with Parking! has air conditioning, a patio, and city views.

FAQ about holiday rentals in Key West









Holiday rentals that guests love in Key West

  • Avg. price/night: £317.47
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 268 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!
    lisa
    Solo traveller
  • Avg. price/night: £282.99
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 2,506 reviews
    the villa was beautiful, we loved the privacy it provided.
    J
    John
    Family with young children
  • Avg. price/night: £215.27
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 1,068 reviews
    Excellent holiday home. I recommend it to everyone.
    Aleksei_LA
    Solo traveller
  • 10
    Scored 10
    Exceptional
    Rated exceptional
     · 5 reviews
    This was an incredible holiday studio! It was very well equipped, very clean, spacious, beautifully decorated and in a fantastic part of town. The hosts were unbelievably helpful and responsive on messaging at all times. The bicycles they provided with the studio were so much appreciated for getting around Key West. The bed was super comfy and the studio is very quiet. Full kitchen provided if you wanted to cook. Top notch air con. Honestly never had a better holiday rental and cannot recommend it more highly! Would return in a heartbeat.
    Lucy
    Young couple
  • Avg. price/night: £280.33
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 2,507 reviews
    The pools were very nice. I absolutely loved the views from our Villa. The staff was very accommodating to all of our needs (we had 8 ladies, so we needed a lot of towels), ha ha.
    Aubrey
    Group
  • Avg. price/night: £264.31
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 2,795 reviews
    Quaint upscale Hotel, felt like a Villa. Rooms were nice, comfortable beds, modern decor. Excellent room service. Breakfast included was good and like happy hour 5-6 with complementary wine. Staff was polite and professional. Nice pool area. I would definitely consider coming back.
    susan
    Young couple
  • 9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 352 reviews
    Clean, warm, cozy! The little unexpected extras make “Key West Villas” stand-out! Towels, fresh & clean, linens soft cotton and comfy, “shot of the day”, snacks, beverages! Heather and Kevin are doing it right!
    M
    Michelle
    People with friends
  • Avg. price/night: £280.33
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 2,507 reviews
    Location was great. Shuttle was convenient and the driver was very friendly and accommodating. Staff was great and our villa was clean, comfortable and roomy. We enjoyed our stay
    Rita
    Group
  • Avg. price/night: £317.47
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 268 reviews
    The location was absolutely perfect and close to all major points of interest. The villa was spacious and provided all needed amenities. The balcony overlooking the pool was beautiful and relaxing. The property was secure with gate codes to enter.
    S
    Susan
    Family with young children
  • Avg. price/night: £280.33
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 2,507 reviews
    The 4 pools were nice and the 2 bedrooms villas were good for our family. Good location away from Duval and walking distance to shopping centers and walking path
    Senta
    Family with young children

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