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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.

Room- loved being adjacent to the pool and off to the side of the property. grounds were very beautiful. Staff was very friendly. Breakfast was very good.

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9.2
Superb
1,152 reviews
Price from
US$231.58
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.

very nice place to stay. Walking distance to most best places to eat and walk.

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9.1
Superb
179 reviews
Price from
US$285.11
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.

Excellently located on the doorstep of the old port, beautiful Wooden old estate, gracefully conserved.

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9.3
Superb
427 reviews
Price from
US$247.50
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
135 reviews
Price from
US$302.62
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.

Lovely and beautiful house with cute furnitures. They have lovely garden and poor, very good and quiet location. Staffs are very friendly.

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9.3
Superb
235 reviews
Price from
US$225
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.

walking distance to everything

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9
Superb
964 reviews
Price from
US$207
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.

Amazingly welcoming staff and incredible amenities. Such a fun atmosphere with their snacks, happy hour, pool, and great owners!

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9.7
Exceptional
352 reviews
Price from
US$280.12
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
US$322.03
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.

Beautiful little oasis in the heart of Key West. Very laid back and only a moment away from the vibrant Duvall Street! Happy hour was lovely and Izabella was so welcoming.

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9.4
Superb
109 reviews
Price from
US$316.88
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.

Loved the whole experience it was so homely and friendly , very attentive staff , everywhere was clean and tidy , x

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9.2
Superb
678 reviews
Price from
US$186.93
per night

Most booked holiday rentals in Key West this month

Enjoy breakfast in Key West!

  • Marreros Guest Mansion - Adult Only
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 135 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
     · 964 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
     · 678 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

  • Alexander's Gay Lesbian Guesthouse (Adult Only 21+)
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 40 reviews

    Set in a 3-story, conch-style home in Key West, Alexander's Gay Lesbian Guesthouse (Adult Only) offers air-conditioned guestrooms with free WiFi.

    Fantastic location with excellent tropical breakfast

  • 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.

  • Authors Key West Guesthouse
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 1,272 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.

  • 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!!!

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.

  • 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

  • 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.

  • 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.

Highly rated holiday rentals in Key West

  • The Speakeasy Inn and Rum Bar
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 179 reviews

    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.

    Excelente quarto, muito confortável e ótima localização

  • Seaport Inn
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 320 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

  • Duval House
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 861 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

  • Road's End by Brightwild
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 6 reviews

    Located within the Downtown Key West district in Key West, Road's End by Brightwild has air conditioning, a patio, and city views.

  • The Barbados by Brightwild-Bright Condo w Pool
    8.1
    Scored 8.1
    Very good
    Rated very good
     · 59 reviews

    Set in Key West, 6.5 km from Southernmost Point and 7.3 km from Ernest Hemingway Home and Museum, The Barbados by Brightwild-Bright Condo w Pool offers air conditioning.

    We had a chance to stay in Key West for reasonable price

  • The Trinidad by Brightwild-Pool & Parking
    8.1
    Scored 8.1
    Very good
    Rated very good
     · 27 reviews

    Boasting air-conditioned accommodation with a patio, The Trinidad by Brightwild-Pool & Parking is situated in Key West.

FAQ about holiday rentals in Key West









Holiday rentals that guests love in Key West

  • Avg. price/night: US$403.88
    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: US$360.01
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 2,505 reviews
    the villa was beautiful, we loved the privacy it provided.
    J
    John
    Family with young children
  • Avg. price/night: US$279.52
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 1,065 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: US$289.13
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 2,508 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: US$336.24
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 2,801 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: US$289.13
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 2,508 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: US$403.88
    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: US$289.13
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 2,508 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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