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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, service, breakfast and location were all amazing! Literally couldn't fault a thing. One of the best places we have stayed!

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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.

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

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9.1
Wonderful
160 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
$285
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 location is amazing and the staff is lovely. The building is really cool, not a ‘hotel’ experience

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9.4
Wonderful
140 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.

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
Wonderful
234 reviews
Price from
$250
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.

Everything was PERFECT and beyond our expectations. The room and the manor was so cute and clean. The breakfast was amazing too! Also, Rachel was amazing to us, she made us feel like home. She was so nice. Thank you for the wonderful stay and we will come back for sure!

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9
Wonderful
951 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.

Location location location. Center of Duval st was fantastic

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9.7
Exceptional
346 reviews
Price from
$379
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
141 reviews
Price from
$423.75
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
Wonderful
105 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.

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
677 reviews
Price from
$234.19
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

  • Old Town Manor
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 950 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
     · 677 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
     · 1,385 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
     · 1,252 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
     · 1,437 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
    8.6
    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!!!

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

  • Duval Street Suite with pool
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 6 reviews

    Duval Street Suite with pool offers accommodations in Key West, a 9-minute walk from Southernmost Point and 0.8 miles from Mallory Square.

  • 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
     · 884 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
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 264 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
     · 558 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
    Excellent
    Rated excellent
     · 593 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

  • The Speakeasy Inn and Rum Bar
    9.1
    Scored 9.1
    Wonderful
    Rated wonderful
     · 160 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

  • Bahama House
    9.1
    Scored 9.1
    Wonderful
    Rated wonderful
     · 8 reviews

    Featuring air conditioning, Bahama House is located in Key West, just 219 yards from Duval Street. Ernest Hemingway Home and Museum is 328 yards away. All units have a TV and DVD player.

  • Seaport Inn
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 337 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
     · 845 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.

FAQ about vacation rentals in Key West









Vacation Rentals That Guests Love in Key West

  • Avg. price/night: $390.38
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 2,426 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
     · 163 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: $390.38
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 2,426 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: $390.38
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 2,426 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: $471.38
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 264 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: $471.38
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 264 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: $471.38
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 264 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
  • 9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 346 reviews
    Excellent location and villa setup. We loved the porch.
    Olga
    Family with young children
  • Avg. price/night: $390.38
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 2,426 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
     · 2,910 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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