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The 10 Best Holiday Rentals in Key West, USA

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.

Very spacious and staff were extremely helpful and courteous.

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9.2
Superb
1,161 reviews
Price from
£259
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.

The location was excellent. The room fit my needs. I like it quiet. Loved the rum bar. Lots of happy people there. I would stay there again.

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9.1
Superb
144 reviews
Price from
£257
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.

Tracey and Glen were awesome hosts. The complimentary happy hour was a nice unexpected surprise

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9.3
Superb
436 reviews
Price from
£298
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.

We had time to spare in Florida before leaving for NYC, we decided to spend 2 nights in Key West and this place was great. Very charming and well decorated.

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9.4
Superb
140 reviews
Price from
£261
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
231 reviews
Price from
£262
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.

one of the most authentic and best places we’ve ever slept. really an amazing experience. breakfast was awesome as well.

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9
Superb
948 reviews
Price from
£196
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.

Everything! Complimentary wine, happy hours, snacks, good breakfast, amenities, clean clean clean, run by wonderful folks.

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9.7
Exceptional
337 reviews
Price from
£297
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
141 reviews
Price from
£349
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.

Even though the hotel is located on Duval street, you hear nothing! Quiet, peaceful, clean. Izabella and Alfredo were amazing and very helpful. We parked our car without any issues, and never needed it until the end of our holiday. Breakfast was delicious, with lots of food to choose from.

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9.4
Superb
103 reviews
Price from
£310
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
672 reviews
Price from
£259
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
     · 140 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!!

  • Key West Bed and Breakfast
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 231 reviews

    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...

    Nice and quiet room, warm breakfast. Friendly staff.

  • The Grand Guesthouse
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 672 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
     · 41 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
     · 1,378 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
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 1,242 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
     · 1,433 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
     · 436 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
    9.1
    Scored 9.1
    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...

  • The Andros by Brightwild-4th Floor Sunset View
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 31 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
     · 878 reviews

    Located in the centre of Key West, just 300 metres from South Beach and 700 metres from Higgs Beach, Alexander Palms Court - No Hidden Resort Fees!

    Quit place close to centre with nice swimming pool

  • 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
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 259 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
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 589 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

  • Westwinds Inn
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 1,138 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.

    Beautiful landscape and quaint feeling overall. Excellent location.

  • Caribbean House
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 556 reviews

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

    The location was excellent. Breakfast was as expected

  • Seaport Inn
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 339 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
     · 388 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.

    Clean, quiet, laid back and had a great onsite mgr- Sam.

  • Old Town Suites
    8.1
    Scored 8.1
    Very good
    Rated very good
     · 378 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
     · 290 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.

    Check-in was easy and everybody made us feel at home

  • Duval House
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 846 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

  • Ambrosia Key West
    8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 811 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.

    Breakfast was just right and delivered to our room

FAQ about holiday rentals in Key West









Holiday rentals that guests love in Key West

  • Avg. price/night: £866.88
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 259 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: £349.83
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 2,349 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
  • Avg. price/night: £404.33
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 160 reviews
    Very nice small hotel in a historic villa house, in a splendid and very calm neighborhood. Extremely nice and kind hosts. You feel like being at your friends house. Parking available on the street around the corner, and all locations including harbour, seafront and Duval street in easy walking distance.
    Martin
    Young couple
  • Avg. price/night: £333.55
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 1,084 reviews
    Staff were very nice and the grounds were excellant ; pool was nice with towels and a great grounds keeper. Bike rental was of great value in Key west. Management did buy a make shift set of a storage dresser but that was more for a attic storage, I would go back there with another room that had closet and dresser space. management needs to renovate bathroom way beyond its life. Nice villa buy a little money spent could make this stay go from a 2 rating to a 10 rating. Owner needs to open his or her wallet
    Frank
    Young couple
  • Avg. price/night: £349.83
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 2,349 reviews
    Beautiful lush gardens. Hotel looks like individual villas surrounding a courtyard of gardens and pools. Room was spacious and we had a beautiful view of the ocean with a private deck and chairs.
    Kara
    Young couple
  • 9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 337 reviews
    The couple who run the villas are charming. They greeted us with cocktails and made us feel comfortable at all times. The place is beautiful and the location is fantastic, just off the main street in Key West.
    Marc
    Young couple
  • Avg. price/night: £866.88
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 259 reviews
    Everything!!!We loved everything about Rose Lane & especially our Villa Alta. It exceeded our expectations.
    Steven
    Young couple
  • 9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 337 reviews
    The location is great! The villas are comfortable and clean. They offer a free happy hour everyday and a shot of the day! We had an amazing time here and would definitely come back!
    Courtney
    Young couple
  • 9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 337 reviews
    We really enjoyed our stay at the Key West Villas. The hosts were so pleasant and the happy hour and shot of the day were a really nice touch to make the stay more welcoming. The accommodations were nice and it was a great location.
    Emily
    Group
  • Avg. price/night: £349.83
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 2,349 reviews
    Very relaxing, we felt at home. The layout of the property was villa style with your own backyard to relax on. The hammock was an extra touch. We loved it! Special thanks to Ms Dori Morton for making it enjoyable.
    Morton
    Family with young children

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