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The 10 Best Vacation Rentals in Key West, USA

Check out our selection of great vacation rentals in Key West

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Wonderful: 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
Wonderful
1,147 reviews
Price from
$309.35
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, the room was so cozy and clean. Also the staff very kind and helpful

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9.1
Wonderful
158 reviews
Price from
$279
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.

Great location, close to all the action yet quiet. Amazing, friendly stuff.

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9.3
Wonderful
428 reviews
Price from
$300
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
Wonderful
139 reviews
Price from
$279
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.

Great breakfast... very nice host and very clean & tidy

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9.3
Wonderful
234 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.

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

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9
Wonderful
949 reviews
Price from
$189
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.

Key West Villas was the best. Kevin & Heather were very gracious hosts and couldn't have been any better. We loved it there. Loved the location, right off Duvall but yet still quiet. Loved the shot of the day, Happy Hour. Every day The pool&hot tub were so relaxing. Our room with king bed was perfect & very clean and comfortable. The front porch was another great relaxing spot, eating from the great selection of breakfast goodies getting to meet other people staying there having great conversations.

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9.7
Exceptional
344 reviews
Price from
$399
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
Wonderful
140 reviews
Price from
$361.25
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
Wonderful
105 reviews
Price from
$281.67
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.

Lovely owner, neat and tidy housing, quiet location, rich breakfast, free parking lots in front of the hotel, late check-in no problem

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9.2
Wonderful
676 reviews
Price from
$281.21
per night

Most booked vacation rentals in Key West this month

Enjoy breakfast in Key West!

  • Southernmost Point Guest House & Garden Bar
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 1,147 reviews

    This Key West, Florida Southernmost Point Guest House & Garden Bar is located on Duval Street 361 feet from the Southernmost Point and 240 feet from the beach.

    The room was spectacular and breakfast was delicious

  • Marreros Guest Mansion - Adult Only
    9.4
    Scored 9.4
    Wonderful
    Rated wonderful
     · 141 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
    Wonderful
    Rated wonderful
     · 949 reviews

    This adult-only, pet friendly, smoke-free property is located in the heart of Key West less than 1 mi from the Southernmost Point.

    Climate place :) Great breakfast in the garden :)

  • The Grand Guesthouse
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 676 reviews

    This adults-only 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
    Wonderful
    Rated wonderful
     · 42 reviews

    This adult-only Conch House Heritage Inn offers accommodations 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
    Excellent
    Rated excellent
     · 1,381 reviews

    Located in Key West, 1969 feet from Key West Aquarium and 1969 feet from Mallory Dock, L'Habitation Guest house- Adult Exclusive provides accommodations 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
     · 1,251 reviews

    Authors Key West Guesthouse features free Wifi and rooms with air conditioning in Key West.

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

  • Courtney's Place Historic Cottages & Inns
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 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.

These vacation rentals in Key West have options with FREE cancellation

  • Key West Harbor Inn - Adults Only
    9.3
    Scored 9.3
    Wonderful
    Rated wonderful
     · 429 reviews

    Key West Harbor Inn - Adults Only in Key West provides adults-only accommodations with an indoor pool, an open-air bath, and a garden.

    very nice and beautiful place with a perfect location

  • Sky Loft in Key West by Brightwild
    9.1
    Scored 9.1
    Wonderful
    Rated wonderful
     · 8 reviews

    Sky Loft in Key West by Brightwild offers accommodations in Key West, a 9-minute walk from Ernest Hemingway Home and Museum and 0.7 miles from Mallory Square.

  • The Andros by Brightwild-4th Floor Sunset View
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 30 reviews

    The Andros by Brightwild-4th Floor Sunset View is located in Key West, just 4 miles from Southernmost Point and 4.6 miles from Ernest Hemingway Home and Museum.

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

  • Alexander Palms Court - No Hidden Resort Fees!
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 885 reviews

    Alexander Palms Court - No Hidden Resort Fees! enjoys a location in Key West, a 6-minute walk from Southernmost Point and 0.7 miles from Ernest Hemingway Home and Museum.

    Great location, very nice, close to everything by foot

  • Weatherstation Inn Circa 1911
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 223 reviews

    Set within 1640 feet 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
    Excellent
    Rated excellent
     · 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 1.1 mi from the Southernmost Point.

    clean. well equipped and the location was amazing.

  • The Casablanca Hotel
    Free cancellation options available
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 559 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
    Excellent
    Rated excellent
     · 592 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 vacation rentals in Key West

  • Seaport Inn
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 335 reviews

    Located in the heart of the historic Seaport District in Old Town, Seaport Inn features an outdoor pool and barbecue and is 1969 feet' walk from Mallory Dock.

    Nice location and good impression of Key West Living

  • The Garden House
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 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
    8.1
    Scored 8.1
    Very Good
    Rated very good
     · 385 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
    Excellent
    Rated excellent
     · 848 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

  • 8.3
    Scored 8.3
    Very Good
    Rated very good
     · 18 reviews

    King Suite Balcony by Brightwild- at James House is located in Key West, just a 5-minute walk from Key West Aquarium and 400 yards from Mallory Dock.

    חדר נעים מיקום מצויין קרוב למקומות העניין המרכזיים בקיי וסט.

  • 8.0
    Scored 8.0
    Very Good
    Rated very good
     · 8 reviews

    Deluxe King with Balcony by Brightwild- at James House with Parking! is located in Key West, just a 5-minute walk from Key West Aquarium and 400 yards from Mallory Dock.

  • Bermuda Suite by Brightwild
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 5 reviews

    Bermuda Suite by Brightwild is located in Key West, just a 3-minute walk from Ernest Hemingway Home and Museum and half a mile from Southernmost Point.

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

    The Barbados by Brightwild-Bright Condo w Pool is located in Key West, just 4 miles from Southernmost Point and 4.6 miles from Ernest Hemingway Home and Museum.

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

FAQ about vacation rentals in Key West









Vacation Rentals That Guests Love in Key West

  • Avg. price/night: $538.88
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 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: $491.63
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 2,414 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: $523.06
    9.4
    Scored 9.4
    Wonderful
    Rated wonderful
     · 162 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: $370.13
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 1,080 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: $491.63
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 2,414 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
  • Avg. price/night: $392.63
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 344 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: $538.88
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 263 reviews
    Everything!!!We loved everything about Rose Lane & especially our Villa Alta. It exceeded our expectations.
    Steven
    Young couple
  • Avg. price/night: $392.63
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 344 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
  • Avg. price/night: $392.63
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 344 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: $491.63
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 2,414 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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