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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.

Great location at the quiet end of Duval.

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9.2
Superb
1,152 reviews
Price from
€ 238
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.

Loved the location and friendly staff. Very laid back like stepping back in time

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9.1
Superb
170 reviews
Price from
€ 242
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.

Everything about this place is just perfect. The location, the staff, the rooms, the beds. Only 2 blocks away from the happening Duval street. Super close to Fury water sports, wherein you could indulge in water sports activities and boat tours with live music. Surrounded by palm trees, the property gives you a tropical feel. Prepared to be greeted by Mango and Mojito, two beautiful cats on premise.

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9.3
Superb
430 reviews
Price from
€ 286
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
137 reviews
Price from
€ 290
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.

Perfekt stay. The rooms are very nice and clean. The breakfast was exceptionell. Fruit salad, orange Juice, granola, fresh cake and delicious bagels. And everything with real plates, no plastic. Bella the Host was wunderful. Super nice and helpful. The location was perfect. You could walk everywhere

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9.3
Superb
237 reviews
Price from
€ 280
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
954 reviews
Price from
€ 227
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.

Location location location. Center of Duval st was fantastic

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9.7
Exceptional
349 reviews
Price from
€ 259
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.

Great location, hotel staff were amazing and gave a lot of useful advise on the area. This is a great hotel with lots of character and charm.

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9.1
Superb
143 reviews
Price from
€ 427
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
107 reviews
Price from
€ 318
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.

Great Guest House. Rooms are lovely, good location and exceptional staff.

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9.2
Superb
677 reviews
Price from
€ 243
per night

Most booked holiday rentals in Key West this month

Enjoy breakfast in Key West!

  • Key West Bed and Breakfast
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 237 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...

    Private feel, cosy, little balcony and nice backyard

  • Old Town Manor
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 954 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

  • 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
     · 1,260 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
     · 1,435 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.

  • Nyah - Adult Exclusive
    7.5
    Scored 7.5
    Good
    Rated good
     · 1,993 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.

    The way the rooms, pools and gardens were set out.

  • Southernmost Point Guest House & Garden Bar
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 1,152 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

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
     · 430 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

  • 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
     · 886 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!

    Great location, very nice, close to everything by foot

  • Rose Lane Villas
    Free cancellation options available
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 263 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

  • King Suite Balcony by Brightwild- at James House
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 20 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.

  • Road's End by Brightwild
    Free cancellation options available
    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 Trinidad by Brightwild-Pool & Parking
    Free cancellation options available
    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.

Highly rated holiday rentals in Key West

  • Westwinds Inn
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 1,105 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.

    Adequate breakfast,muffins ,cereal eggs ,jam etc .Lovely pool

  • Seaport Inn
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 330 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

  • Old Town Suites
    8.1
    Scored 8.1
    Very good
    Rated very good
     · 394 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

  • The St Martin by Brightwild-Hot Tub & Pool
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 6 reviews

    Located in Key West in the Florida region, The St Martin by Brightwild-Hot Tub & Pool has a patio. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

  • The Salt Cay by Brightwild-Modern & Pet Friendly
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 18 reviews

    Boasting air-conditioned accommodation with a patio, The Salt Cay by Brightwild-Modern & Pet Friendly is set in Key West.

    Clean, had kitchen and laundry, more than one bathroom

  • Traveler's Palm by Brightwild
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 31 reviews

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

    Sehr gemütlich. Mit toller kleiner Dachterrasse mit Hängematte.

  • The Indigo by Brightwild-Great Location!
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 6 reviews

    In the heart of Key West, set within a short distance of South Beach and Fort Zachary Taylor State Park Beach, The Indigo by Brightwild-Great Location!

  • Coral Cove #1 by Brightwild
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 6 reviews

    Set within the Downtown Key West district in Key West, Coral Cove #1 by Brightwild has air conditioning, a patio, and city views.

FAQ about holiday rentals in Key West









Holiday rentals that guests love in Key West

  • 8.3
    Scored 8.3
    Very good
    Rated very good
     · 1,074 reviews
    Excellent holiday home. I recommend it to everyone.
    Aleksei_LA
    Solo traveller
  • Avg. price/night: € 344.14
    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: € 298.02
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 2,463 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: € 310.36
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 2,774 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
     · 349 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: € 298.02
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 2,463 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: € 403.94
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 263 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: € 298.02
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 2,463 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: € 261.68
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 166 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: € 310.48
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 1,088 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

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