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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.

Breakfast was good, people where friendly and the room was really beautifull

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9.2
Wonderful
1,146 reviews
Price from
$286.35
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 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
Wonderful
163 reviews
Price from
$229
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
Wonderful
430 reviews
Price from
$275
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
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.

Private feel, cosy, little balcony and nice backyard

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9.3
Wonderful
234 reviews
Price from
$270
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
953 reviews
Price from
$179
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.

Friendly staff and complimentary breakfast

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9.7
Exceptional
348 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
144 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 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
107 reviews
Price from
$306.27
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 guesthouse with nice room, a porch outside the room for relax. Breakfast with bagels, yoghourt, juice and coffee available around the clock. And the location of the guesthouse is calm and close to Key West day-and nightlife. Bicycles for hire

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9.2
Wonderful
676 reviews
Price from
$197.01
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
     · 139 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
    Wonderful
    Rated wonderful
     · 234 reviews

    Featuring garden views, Key West Bed and Breakfast in Key West features accommodations and a garden. The air-conditioned accommodations are a 19-minute walk from South Beach.

    Private feel, cosy, little balcony and nice backyard

  • 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
     · 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
     · 41 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.

  • 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.

  • Weatherstation Inn Circa 1911
    8.5
    Scored 8.5
    Very Good
    Rated very good
     · 224 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!!!

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
     · 430 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
     · 881 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

  • 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

  • La Pensione Inn - Adult Exclusive
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 594 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.

  • 8.4
    Scored 8.4
    Very Good
    Rated very good
     · 19 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.

Highly-rated vacation rentals in Key West

  • Westwinds Inn
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 1,110 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.

  • Seaport Inn
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 336 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
     · 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.

    The staff is very friendly, and is a beautiful place

  • Old Town Suites
    8.1
    Scored 8.1
    Very Good
    Rated very good
     · 390 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
     · 288 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
    Excellent
    Rated excellent
     · 844 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

  • 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
    8.1
    Scored 8.1
    Very Good
    Rated very good
     · 27 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.

FAQ about vacation rentals in Key West









Vacation Rentals That Guests Love in Key West

  • Avg. price/night: $345.38
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 2,449 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
  • 9.4
    Scored 9.4
    Wonderful
    Rated wonderful
     · 164 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: $345.38
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 2,449 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: $345.38
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 2,449 reviews
    The location is nice and we got a 3 bedroom villa for 3 people to spread out in. The shuttle to the beach is a nice benefit. Pools are lovely.
    Swati
    Travelers with friends
  • Avg. price/night: $358.88
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 263 reviews
    The place was located perfectly. Steps away from Duval. The staff was friendly. I received everything I needed by email. The Villas were perfect.
    McCoach
    Group
  • Avg. price/night: $358.88
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 263 reviews
    The villa was exactly as stated. Clean, comfortable and walking distance to all there is to do on Duval Street.
    Susan
    Group
  • Avg. price/night: $358.88
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 263 reviews
    I like the style of villa. Comfortable bed. Big tarras. The location, close to everything. Our apartment 25 was very spacious
    Władysław
    Family with young children
  • Avg. price/night: $336.38
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 348 reviews
    Excellent location and villa setup. We loved the porch.
    Olga
    Family with young children
  • Avg. price/night: $345.38
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 2,449 reviews
    Liked the villa style rooms and furnishings. 2 bed villas was very modern and spacious. Hammocks and sunset by the beach was the best They had 4 separate pools though were on the smaller side but great for privacy
    Joanne
    Family with young children
  • Avg. price/night: $358.88
    7.9
    Scored 7.9
    Good
    Rated good
     · 2,915 reviews
    Location was great....we stayed in the Heather villa which is the biggest one they have. Nice set up with a private hot tub
    Angela
    Family with young children

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