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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.

The room was spacious and was very clean. The maid was very nice and the check-in clerk was friendly and helpful. The bar was loud but shut down at 7 so it was not a nuisance.

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9.2
Wonderful
1,150 reviews
Price from
$343.85
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 vibe! We stayed in a renovated room. Unfortunately we just stayed there for one night!

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9.1
Wonderful
149 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.

- room was great! Comfy, clean and tidy and a great bathroom. - location is amazing. Right next to the harbour and less than 10min walk to Duval Street. It was also still very quiet and relaxing. - the inside ground/courtyard were nice and gave a greenery and isolation even though in the center of town. Great to chill by the pool. - complementary drinks for happy hour! The rum punch was great and went down way to easily! - the staff was very friendly, especially Stacey who was very friendly and helpful. - friendly guests, it seemed that all the guests there were on the same wavelength and it was great to have a chat at breakfast or during happy hour

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9.3
Wonderful
431 reviews
Price from
$305
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.

The staff was very welcoming and probably the best part. Jayme helped check me in and was great to talk to but what really got me was when she took the time to mail something we forgot at the hotel (we had already gotten back to Miami by the time we realized we forgot something). I just called and gave her the address and it was mailed out the next day. We were in the Amistad room and it was super cute and super clean. The hotel was in a great location and easy to get to where we needed, walked everywhere for the most part. The pool is 24 hours which is great even though my gf and I didn't really get a chance to use it. Free water and soda is something that I don't really think about but turned out to be a great perk because most places charge for extra beverages (my gf loves sprite and with the summer heat the water was welcomed).

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9.4
Wonderful
141 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.

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

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9.4
Wonderful
230 reviews
Price from
$290
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.

Really clean and comfortable. Calm environment. Close to everything

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9
Wonderful
952 reviews
Price from
$239
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
$299
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.

The service of the staff is outstanding. They made us feel special and at home from the first minute. The house has a very interesting history and famous thrilling story but you need to hear it first hand. The rooms are large and very comfortable. All well airconditioned. The location is excellent and close to the main attractions. The breakfast are excellent with a wide selection. The selection of coffee is also excellent. Happy hour at 4pm is brilliant and the hosts are very generous with wine, beer , cake and other snacks. The splash pool was a life saver. The one day was 100+F and we spent 3 hours in the pool cooling down. It was such a social occasion with other guests.

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9.1
Wonderful
139 reviews
Price from
$386.25
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 location is pretty central. The place itself is cute. We met Alredo and Isabella briefly, both sweet and welcoming. Happy hour starting at 3—bucketful of wine and beer. There’s an ice machine and water dispenser by the pool.

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9.4
Wonderful
104 reviews
Price from
$343.17
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.

Everything was perfect, since the welcoming up to the farewell. The room very comfortable, the excellent breakfast and the quietness of the localization.

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9.2
Wonderful
675 reviews
Price from
$281.21
per night

Most booked vacation rentals in Key West this month

Enjoy breakfast in Key West!

  • 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
     · 952 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
     · 675 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

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

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

    Fantastic location with excellent tropical breakfast

  • Authors Key West Guesthouse
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 1,247 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
     · 1,430 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.

  • New Orleans House - Gay Male Adult Guesthouse
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 291 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

  • La Pensione Inn - Adult Exclusive
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 584 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.

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
     · 432 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

  • 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
     · 879 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

  • Rose Lane Villas
    Free cancellation options available
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 258 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
     · 557 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
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 17 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.

    location was fabulous. room easy to get into and was comfortable

  • Deluxe King with Balcony by Brightwild- at James House with Parking!
    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.

Highly-rated vacation rentals in Key West

  • The Speakeasy Inn and Rum Bar
    9.1
    Scored 9.1
    Wonderful
    Rated wonderful
     · 149 reviews

    The Speakeasy Inn and Rum Bar features accommodations within 500 yards of the center of Key West, with free Wifi and a kitchenette with a microwave, a fridge, and kitchenware.

    Excelente quarto, muito confortável e ótima localização

  • Westwinds Inn
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 1,132 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.

  • 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

  • The Trinidad by Brightwild-Pool & Parking
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 25 reviews

    The Trinidad by Brightwild-Pool & Parking offers accommodations in Key West, 4 miles from Southernmost Point and 4.6 miles from Ernest Hemingway Home and Museum.

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

    The St Martin by Brightwild-Hot Tub & Pool offers accommodations in Key West, 4 miles from Southernmost Point and 4.6 miles from Ernest Hemingway Home and Museum.

  • The Tortuga by Brightwild-Pool, Parking & Pets!
    8.4
    Scored 8.4
    Very Good
    Rated very good
     · 22 reviews

    The Tortuga by Brightwild-Pool, Parking & Pets! is located in Key West, just 4 miles from Southernmost Point and 4.6 miles from Ernest Hemingway Home and Museum.

    Clean and had just what we needed for a short trip

  • The Salt Cay by Brightwild-Modern & Pet Friendly
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 18 reviews

    The Salt Cay by Brightwild-Modern & Pet Friendly offers accommodations in Key West, 4 miles from Southernmost Point and 4.6 miles from Ernest Hemingway Home and Museum.

    Clean, had kitchen and laundry, more than one bathroom

  • Villa Coastal by Brightwild-Pool & Free Parking
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 14 reviews

    Villa Coastal by Brightwild-Pool & Free Parking offers accommodations in Key West, a 6-minute walk from Duval Street and 700 yards from Southernmost Point.

FAQ about vacation rentals in Key West









Vacation Rentals That Guests Love in Key West

  • Avg. price/night: $471.38
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 258 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: $435.38
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 2,369 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: $460.69
    9.4
    Scored 9.4
    Wonderful
    Rated wonderful
     · 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: $898.88
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 1,081 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: $435.38
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 2,369 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: $471.38
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 258 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: $435.38
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 2,369 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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