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The 10 Best Vacation Homes in Key West, USA

Check out our selection of great vacation homes in Key West

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Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
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Located in the heart of historic Key West, guests will be 1 minutes’ walk from Duval Street. A heated pool, daily continental breakfast, and free WiFi are provided.

All rooms feature a private bath, small refrigerator, and microwave. Apartments at Key West Villas include a fully-equipped kitchen and seating area.

Location location location. Center of Duval st was fantastic

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9.7
Exceptional
346 reviews
Price from
$379
per night

Popular points of interest near the holiday home include Ernest Hemingway Home and Museum, Duval Street and Southernmost Point. The nearest airport is Key West International Airport, 4 km from Just steps to Duval- Sleeps 10- Heated Pool House.

Location was awesome. Beds comfortable. Had everything we needed.

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9.8
Exceptional
5 reviews
Price from
$896
per night

Featuring a DVD player, the holiday home has a fully equipped kitchen with a dishwasher, an oven and a microwave, a living room with a seating area and a dining area, 2 bedrooms, and 2 bathrooms with a hot tub and a shower. The unit is air conditioned and includes a balcony with outdoor furniture as well as a flat-screen TV with cable channels. For added privacy, the accommodation features a private entrance.

I loved everything about it.The place was so gorgeous and clean.The customer service was excellent.The master bedroom has a his and hers sink in the bathroom the shower was very big and nice.If I come back to Key West again I will choose to stay at this beautiful condo again.

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9.4
Wonderful
5 reviews
Price from
$461.38
per night

The spacious holiday home features 3 bedrooms, a TV, a fully equipped kitchen with an oven and a microwave, and 4 bathrooms with an a bath or shower. Towels and bed linen are provided in the holiday home. For added privacy, the accommodation features a private entrance.

This is a perfect spot to stay in Key West. Great location - just a couple minutes walk to Duval Street. We rent entire unit and it was amazing. Apartments are clean, beautiful cuban style. we spend there only 2 night but it was amazing experience. Highly recommend it!

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9.8
Exceptional
6 reviews

The spacious holiday home features 2 bedrooms, a flat-screen TV with cable channels, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a bath. Towels and bed linen are featured in the holiday home. For added privacy, the accommodation features a private entrance.

Close to the ocean. Large rooms

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9.5
Exceptional
8 reviews
Price from
$364.62
per night

The spacious holiday home features 2 bedrooms, a TV, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a bath. Guests can take in the ambience of the surroundings from an outdoor dining area.

Location was perfect pool looked amazing

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9.5
Exceptional
6 reviews
Price from
$519
per night

Located in the centre of Key West, 600 metres from Fort Zachary Taylor State Park Beach and 1.2 km from Simonton Street Beach, Lavender Jungle by AvantStay Great Location w Patio Shared Pool Week Long Stays Only offers free WiFi and air conditioning. This holiday home provides accommodation with a patio. The property is non-smoking and is set 1.5 km from South Beach.

The holiday home features 2 bedrooms, a TV, a fully equipped kitchen with an oven and a fridge, a washing machine, and 1 bathroom with a bath.

Great location. Super helpful staff

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9.8
Exceptional
5 reviews

The 2-bedroom holiday home has a living room with a TV, a fully equipped kitchen with a dishwasher and an oven, and 2 bathrooms with a hair dryer.

Southernmost Point is 2.7 km from the holiday home, while Ernest Hemingway Home and Museum is 3.3 km from the property. The nearest airport is Key West International Airport, 2 km from Papaya Place by AvantStay Great Location w Balcony Outdoor Dining Shared Pool Hot Tub.

Slept 6. There is private and secure parking. This is a big deal in Key West. Full kitchen with everything you need for a family dinner.

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9
Wonderful
5 reviews

The spacious holiday home with a balcony and pool views features 2 bedrooms, a living room, a TV, an equipped kitchen with a dishwasher and an oven, and 2 bathrooms with a walk-in shower. This holiday home also provides guests with a patio that doubles up as an outdoor dining area. For added privacy, the accommodation features a private entrance.

Quiet comfy place just like home

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9.6
Exceptional
7 reviews
Price from
$373.33
per night

The spacious holiday home is equipped with 1 bedroom, 1 bathroom, bed linen, towels, a TV with cable channels, a fully equipped kitchen, and a patio with city views.

The holiday home conveniently has an outdoor pool.

Location, and general layout of the property.

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9.1
Wonderful
8 reviews
Price from
$343
per night

Looking for a vacation home?

Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.
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  • Key West Villas
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 345 reviews

    Located in the heart of historic Key West, guests will be 1 minutes’ walk from Duval Street. A heated pool, daily continental breakfast, and free WiFi are provided.

    the personal touch the service was out of this world

  • Just steps to Duval- Sleeps 10- Heated Pool House
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 5 reviews

    Just steps to Duval- Sleeps 10- Heated Pool House is located in Key West, just a 7-minute walk from Southernmost Point and 0.8 miles from Mallory Square.

    Location was awesome. Beds comfortable. Had everything we needed.

  • Sunrise on the Atlantic
    9.4
    Scored 9.4
    Wonderful
    Rated wonderful
     · 5 reviews

    Sunrise on the Atlantic offers accommodations in Key West, 1.6 miles from Southernmost Point and 2 miles from Ernest Hemingway Home and Museum.

    The available amenities were very nice. The property is well maintained and inviting.

  • Julia Whitehead Guest Suites
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 6 reviews

    Julia Whitehead Guest Suites offers accommodations in Key West, a 6-minute walk from Duval Street and 500 yards from Southernmost Point.

  • Leaward Isle Island Retreat
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 8 reviews

    Leaward Isle Island Retreat offers accommodations in Key West, 1.6 miles from Southernmost Point and 2 miles from Ernest Hemingway Home and Museum.

  • Amelia Home by AvantStay In Historic Old Town w Pool
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 6 reviews

    Amelia Home by AvantStay In Historic Old Town w Pool offers accommodations in Key West, a 7-minute walk from Ernest Hemingway Home and Museum and half a mile from Duval Street.

  • Lavender Jungle by AvantStay Great Location w Patio Shared Pool Week Long Stays Only
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 5 reviews

    Lavender Jungle by AvantStay Great Location w Patio Shared Pool Week Long Stays Only is located in Key West, just a 9-minute walk from Ernest Hemingway Home and Museum and 0.6 miles from Mallory...

  • Papaya Place by AvantStay Great Location w Balcony Outdoor Dining Shared Pool Hot Tub
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 5 reviews

    Papaya Place by AvantStay Great Location w Balcony Outdoor Dining Shared Pool Hot Tub is located in Key West, just 1.7 miles from Southernmost Point and 2.1 miles from Ernest Hemingway Home and Museum...

Save money on vacation homes in Key West – budget options available!

  • Baya House
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 7 reviews

    Baya House offers accommodations in Key West, a 7-minute walk from Duval Street and half a mile from Southernmost Point.

  • Sunrise Suites Cat Island Suite #205
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 5 reviews

    Sunrise Suites Cat Island Suite #205 offers accommodations in Key West, 4 miles from Southernmost Point and 4.6 miles from Ernest Hemingway Home and Museum.

    The location was good! It was nice to be out of the city

  • Crawl to Duval w/ Hot tub
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 6 reviews

    A 7-minute walk from South Beach in Key West, Crawl to Duval w/ Hot tub provides accommodations with access to a hot tub. This property offers access to a terrace and free private parking.

  • Paradise Place by AvantStay Key West Old Town Condo w Shared Pool
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 8 reviews

    Paradise Place by AvantStay Key West Old Town Condo w Shared Pool is located in Key West, just 1.4 miles from Mallory Square and 1.4 miles from Key West Aquarium.

  • 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 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 Exuma Cay by Brightwild-Pool View & Parking
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 14 reviews

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

  • Bahama Gardens - Conch House
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 7 reviews

    Just a 13-minute walk from South Beach and 0.9 miles from Simonton Street Beach, Bahama Gardens - Conch House features accommodations in Key West with free bikes, a garden, and a tennis court.

    The location was perfect, the staff friendly and helpful. Bikes available without costs

Great access to the city center! Check these vacation homes in Key West

  • Keys Please by Brightwild
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 3 reviews

    Keys Please by Brightwild is located in Key West, just a 7-minute walk from Ernest Hemingway Home and Museum and half a mile from Duval Street.

  • Pilar Cottage by Brightwild
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 2 reviews

    Pilar Cottage by Brightwild offers accommodations in Key West, a 6-minute walk from Key West Aquarium and 500 yards from Mallory Dock. This villa features air-conditioned accommodations with a patio.

  • Modern Keys by Brightwild-Waterfront w Dock
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Modern Keys by Brightwild-Waterfront w Dock offers accommodations in Key West, 5.1 miles from Ernest Hemingway Home and Museum and 5.2 miles from Duval Street.

  • The Crestwood House - Private Heated Pool & Parking
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    The Crestwood House - Private Heated Pool & Parking offers accommodations in Key West, 5.2 miles from Ernest Hemingway Home and Museum and 5.3 miles from Duval Street.

  • Smooth Sailing by Brightwild-Pool & Boat Dock
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Smooth Sailing by Brightwild-Pool & Boat Dock offers accommodations in Key West, 5.1 miles from Ernest Hemingway Home and Museum and 5.2 miles from Duval Street.

  • Coastal Bliss by Brightwild-Pool, Parking, Dock!
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Coastal Bliss by Brightwild-Pool, Parking, Dock! offers accommodations in Key West, 5.2 miles from Ernest Hemingway Home and Museum and 5.3 miles from Duval Street.

  • Duval Sea Turtle by AvantStay Great Location Close to Shops Shared Pool
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Duval Sea Turtle by AvantStay Great Location Close to Shops Shared Pool offers accommodations in Key West, a 7-minute walk from Southernmost Point and one mile from Mallory Square.

  • Two Duval Street Suites w parking and pool
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Two Duval Street Suites w parking and pool is located in Key West, just a 9-minute walk from Southernmost Point and 0.8 miles from Mallory Square.

  • Tropical Dreaming by AvantStay 4 BLKS to Beach Private Pool
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 2 reviews

    Tropical Dreaming by AvantStay 4 BLKS to Beach Private Pool offers accommodations in Key West, a 7-minute walk from Ernest Hemingway Home and Museum and half a mile from Duval Street.

  • Contra House by Brightwild-Luxury Home With Pool
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Contra House by Brightwild-Luxury Home With Pool offers accommodations in Key West, a 6-minute walk from Ernest Hemingway Home and Museum and 0.7 miles from Southernmost Point.

  • Bahama Gardens - Turtle House
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Providing an outdoor swimming pool, Bahama Gardens - Turtle House offers accommodations in the center of Key West.

  • Bahama Gardens - Main House
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Just a 14-minute walk from South Beach and 0.9 miles from Simonton Street Beach, Bahama Gardens - Main House features accommodations in Key West with free bikes, a garden, and a tennis court.

  • Villa Positano by Brightwild-Rooftop Pool on Duval
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 4 reviews

    Villa Positano by Brightwild-Rooftop Pool on Duval offers accommodations in Key West, a 6-minute walk from Duval Street and 700 yards from Southernmost Point.

  • 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

  • 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.

  • 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.

  • Helen's Hideaway by Brightwild
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 2 reviews

    Helen's Hideaway by Brightwild offers accommodations in Key West, a 6-minute walk from Ernest Hemingway Home and Museum and 0.7 miles from Southernmost Point.

  • NEW Grenada Suite - Parking Pool & Pets 209
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 2 reviews

    NEW Grenada Suite - Parking Pool & Pets 209 offers accommodations in Key West, 4 miles from Southernmost Point and 4.6 miles from Ernest Hemingway Home and Museum.

  • Casita de Catherine by AvantStay 1 Block to Duval St w Hot Tub
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 1 review

    Casita de Catherine by AvantStay 1 Block to Duval St w Hot Tub offers accommodations in Key West, a 6-minute walk from Ernest Hemingway Home and Museum and 0.4 miles from Duval Street.

  • Key Lime Calypso
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 6 reviews

    Key Lime Calypso is located in Key West, just 219 yards from Ernest Hemingway Home and Museum. Duval Street is 656 yards away. The accommodation is fitted with a TV with satellite channels.

  • Passover Cottage
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 2 reviews

    Passover Cottage is located in Key West, just 656 yards from Ernest Hemingway Home and Museum. Duval Street is half a mile from the property.

  • Rose Lane Villas
    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.

  • New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 3 reviews

    New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool offers accommodations in Key West, a 7-minute walk from Duval Street and 0.4 miles from Southernmost Point.

  • Grand Marina Suite by Brightwild-Waterfront Condo
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 82 reviews

    Grand Marina Suite by Brightwild-Waterfront Condo is located in Key West, just 5.7 miles from Ernest Hemingway Home and Museum and 5.7 miles from Duval Street.

    La cocina y comedor, baños y habitaciones estaban bien

  • 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.

  • The Salt Cay by Brightwild-Modern & Pet Friendly
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 19 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

  • Duval Street Suite overlooking Duval with parking and pool
    8.5
    Scored 8.5
    Very Good
    Rated very good
     · 2 reviews

    Duval Street Suite overlooking Duval with parking and pool is located in Key West, just a 9-minute walk from Southernmost Point and 0.8 miles from Mallory Square.

  • Sunrise Suites Antigua Suite #312
    8.4
    Scored 8.4
    Very Good
    Rated very good
     · 16 reviews

    Sunrise Suites Antigua Suite #312 is located in Key West, just 4.6 miles from Ernest Hemingway Home and Museum and 4.6 miles from Duval Street. Guests are welcome to go for a swim in the heated pool.

    It was very clean and comfortable, and newer and location.

FAQ about vacation homes in Key West







Vacation Homes That Guests Love in Key West

  • Avg. price/night: $382.26
    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: $293.25
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 2,517 reviews
    The location was great and only a short walk to all that Duval Street has to offer. There was tea and coffee available all day which was nice. The pool area and gardens are lovely and very clean. Our room was a great size.
    Susan
    Young couple
  • Avg. price/night: $331.88
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 1,112 reviews
    Cute little resort with two pools surrounded by a botanical garden. The complimentary breakfast in the garden is a plus - thanks Tyron for the great service. Duval Street and all the attractions in the area are within walking distance. The rooms are very clean and the staff is super friendly - thanks Al and team👍☀️
    Marco
    Family with young children
  • Avg. price/night: $427.51
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 2,470 reviews
    The room was a good size and very clean. The pool area was really lovely and made the hotel feel relaxing. You wouldn’t have thought it was on a main road.
    Joanne
    Young couple
  • 8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 1,514 reviews
    Above usual Motel Standart. Very clean! Nice and surprisingly quiet location. Silent A/C. Walking distance to all Key West, in fact strolling though the residential streets was cool. Our daughter loved the pool. Coin laundry on site. Friendly staff. Free parking
    Jan
    Group
  • Avg. price/night: $312.97
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 4,573 reviews
    Great location - walking distance of all major sites in Old Town. Very clean, spacious, modern room. Kids loved pool. Safe parking.
    Jean
    Family with young children
  • Avg. price/night: $312.97
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 4,573 reviews
    The location is excellent. The property is kept very clean. The room was immaculate. Really helpful and friendly staff. The pool was lovely to relax in.
    Sonja
    Family with young children
  • Avg. price/night: $555.49
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 676 reviews
    Great location, very clean and comfortable
    Zoe
    Young couple
  • 9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 2,764 reviews
    Great location, very clean, good parking.
    Alan
    Young couple
  • Avg. price/night: $370.13
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 337 reviews
    Location was great,very clean , cleaning staff was very helpful,Maria
    Haworth
    Young couple

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