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Key West Vacation Rentals & House Rentals - 25 Rentals Available

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25 Vacation rentals

(119)

1 / 28

Key West Apartment

  • 2
  • 6
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
“we can"t say enough about the condo or Pam. She takes good care of her rental. Always clean and comfortable.The balcony overlooks the pool area which is well maintained. Pam is always available to answer any questions you might have. We stay the...”
- Review left on 12/03/2016

$200

Excellent (119 reviews)

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from $200 / night

(7)

1 / 12

Key West Condo

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$275

Very Good (7 reviews)

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from $275 / night

(5)

1 / 14

Key West Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
“We (2 retired couples) enjoyed our stay at Rooster Retreat. What you see in the pictures is true to what you get, but I will add that the "twins to king conversion" is probably the best I have ever experienced. It just did not "feel" like twins --...”
- Review left on 03/12/2017

$186

Very Good (5 reviews)

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from $186 / night

(5)

1 / 15

Key West Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
“We stayed for a week and had a wonderful holiday. The booking and communication with the owner was good and the accommodation is exactly as described. It is a lovely clean well equipped apartment in a central location. Easy walk to all of the...”
- Review left on 07/13/2016

$228

Excellent (5 reviews)

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from $228 / night

(3)

1 / 6

Key West Apartment

  • 2
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$295

Very Good (3 reviews)

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from $295 / night

(17)

1 / 17

Key West Townhouse

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Car not necessary
“This unit was great! The location is fantastic! The condo is spacious, clean and everything we were hoping for. I like that the bedrooms are upstairs which offers more privacy...”
- Review left on 01/12/2017

$200

Excellent (17 reviews)

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from $200 / night

(50)

1 / 36

Key West Condo

  • 2
  • 6
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We enjoyed our stay at the Sunrise Suite. The place was bright with sunshine. It was clean, comfortable, nice sitting balcony and close to Duval Street. It had everything you would need for your stay. You could walk thru the complex and cross the...”
- Review left on 03/06/2017

$209

Excellent (50 reviews)

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from $209 / night

(1)

1 / 23

Key West House

  • 3
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This house is immaculately kept and one of the few houses on a canal in KW. Beautiful interior and plenty of room in the bedrooms. The pool overlooks the canal and has an absolutely beautiful view! If you want a house that makes you feel like you're...”
- Review left on 03/10/2015

$133

Excellent (1 reviews)

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from $133 / night

(6)

1 / 28

Key West Townhouse

  • 2
  • 6
  • Min stay varies
  • Ask about children
  • Air conditioning
“The property was located very close everything we wanted. Didn't really need the golf cart we rented for the week. The townhouse was clean, spacious and comfortable. (although there were a lot of tiny ants , especially in the kitchen) We will...”
- Review left on 11/08/2016

$241

Excellent (6 reviews)

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from $241 / night

(2)

1 / 26

Key West Townhouse

  • 2
  • 6
  • Min stay varies
  • Ask about children
  • Air conditioning

$288

Very Good (2 reviews)

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from $288 / night

(4)

1 / 22

Key West Townhouse

  • 2
  • 6
  • Min stay varies
  • Ask about children
  • Air conditioning
“The property we rented was wonderful. It was very clean and spacious for my family to enjoy while we were attending a wedding. The grounds area was well maintained. Sitting by the pool was relaxing and to see iguanas come right down from the trees...”
- Review left on 05/29/2016

$201

Very Good (4 reviews)

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from $201 / night

1 / 17

Key West House

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning

from $100 / night

(4)

1 / 10

Key West Villa

  • 1
  • 2
  • 7 nights min
  • Ask about children
  • Air conditioning
“I have leased this property and another in Marathon. BOTH are just amazing in every way. Mary and Gabby do everything in their power to make it all perfect... I am returning this winter and have already pre booked for 2017...”
- Review left on 01/06/2016

$170

Excellent (4 reviews)

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from $170 / night

(3)

1 / 55

Key West Villa

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“I rented this house for my sister-in-law's bachelorette weekend. The house was spacious, clean, and overall one of the best houses we've stayed in...”
- Review left on 09/27/2016

$829

Excellent (3 reviews)

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from $829 / night

(3)

1 / 21

Key West Townhouse

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Air conditioning
“Our first trip to key west. We took our 2 teenage daughters. This house had everything needed for a home away from home. The pool was refreshing after a long hot day. Very quiet secluded area, yet Close to everything. Highly recommended. House was...”
- Review left on 06/26/2016

$275

Excellent (3 reviews)

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from $275 / night

(4)

1 / 21

Key West Cottage

  • 1
  • 4
  • Min stay varies
  • Ask about children
  • Air conditioning
“The home was clean and in a great location. Bars are close by and there is a cute grocery store down the street. Parking is limited to only one space so make sure you only have one car when you visit...”
- Review left on 06/05/2016

$221

Very Good (4 reviews)

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from $221 / night

(16)

1 / 21

Key West House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We rented Casa Rosa with three other couples for a week in February, 2017. Location was terrific! We could walk to many restaurants,bars, beaches and one grocery store (Fausto's). Suitable size for 8 people. Liked that each couple had their own...”
- Review left on 03/05/2017

$541

Very Good (16 reviews)

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from $541 / night

(3)

1 / 28

Key West Villa

  • 6
  • 16
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“This house is great for large groups. We had such a fun time having a reunion here. Close to everything, and staff was attentive and friendly...”
- Review left on 09/08/2016

$1195

Excellent (3 reviews)

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from $1195 / night

(2)

1 / 18

Key West Condo

  • 3
  • 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$195

Excellent (2 reviews)

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from $195 / night

(3)

1 / 37

Key West House

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“This home was more than expected. It was close enough to all the night life of Duval Street, yet are enough to enjoy peace and quiet when needed. I would recommend this home to anyone looking for a great vacation getaway...”
- Review left on 05/20/2015

$356

Very Good (3 reviews)

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from $356 / night

(9)

1 / 20

Key West Condo

  • 2
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“Excellent location walking distance to Smather's beach. Gorgeous view of the ocean and perfect location. Full 2 bedrooms and 2 baths as well as a full kitchen and living room. Very clean and modern. Rain Forest pathway to the pool and grilling...”
- Review left on 08/12/2016

$250

Very Good (9 reviews)

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from $250 / night

(2)

1 / 29

Key West Townhouse

  • 3
  • 6
  • 3 nights min
  • Ask about children
  • Air conditioning
“The place was very nize,cozy, clean and comfortable, felt very much at home would definitely come back again and rent the same place”
- Review left on 08/09/2016

$400

Excellent (2 reviews)

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from $400 / night

(2)

1 / 15

Key West Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“My boyfriend and I stayed here for approximately five nights. The condo is situated on the 4th floor with an amazing view of the ocean right out on the balcony. The condo was very clean and well-maintained. All of the appliances worked appropriately...”
- Review left on 01/04/2017

$200

Excellent (2 reviews)

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from $200 / night

(1)

1 / 15

Key West Apartment

  • 1
  • 2
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Ask about children

$60

Excellent (1 reviews)

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from $60 / night

1 / 24

Key West Townhouse

  • 3
  • 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

from $252 / night

Your search has been expanded 20.9 miles to include more rentals

1 / 8

Sugarloaf House - 13.6 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

from $140 / night

1 / 16

Sugarloaf House - 15.1 miles away

  • 4
  • 8
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

from $167 / night

(4)

1 / 3

Summerland Key Guest house - 15.3 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“We rented the Conch House for our honeymoon and it was perfect! We loved the secluded feeling and the private beach. Carol was wonderful to work with and had fresh eggs and champagne waiting for us in our fridge. She picked fresh veggies for us to...”
- Review left on 04/20/2016

$394

Excellent (4 reviews)

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from $394 / night

1 / 17

Sugarloaf House - 15.3 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

from $160 / night

1 / 12

Sugarloaf House - 15.7 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

from $140 / night

1 / 19

Sugarloaf House - 18.1 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

from $189 / night

1 / 11

Cudjoe Key House - 19.6 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

from $167 / night

1 / 14

Cudjoe Key House - 19.6 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

from $120 / night

1 / 19

Cudjoe Key House - 19.6 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

from $180 / night

(48)

1 / 34

Cudjoe Key House - 19.8 miles away

  • 6
  • 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$414

Very Good (48 reviews)

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from $414 / night

1 / 14

Cudjoe Key House - 20.6 miles away

  • 2
  • 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

from $114 / night

1 / 14

Cudjoe Key House - 20.8 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

from $100 / night

1 / 19

Cudjoe Key House - 20.8 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

from $134 / night

1 / 19

Cudjoe Key House - 20.9 miles away

  • 2
  • 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

from $96 / night

1 / 15

Cudjoe Key House - 20.9 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

from $114 / night

About Key West

A laid-back city in the Florida Keys, Key West should be on every traveler's vacation list. With equal parts nature, history, and nightlife, this Florida destination has a little something for everyone.


A Short History of Key West

At the very end of the Florida Keys, this four-square-mile island was first settled by Spanish explorers led by Ponce de León. The remote location was sparsely populated until it was claimed by the United States in the early 19th century. By the turn of the 20th century, Key West was actually the largest and most moneyed city in Florida, thanks to its quick development, naval base, and cigar industry. The locale began to develop its reputation as a tourist hotspot around that time, and this southernmost U.S. city still holds that identity today.


What Key West Does Best

This small island is packed with attractions and activities. Surrounded by the Gulf of Mexico, Key West offers visitors ample natural beauty and great swimming beaches. History buffs love the island’s maritime history and legends of its famous residents, while partygoers can’t get enough of Duval Street, the center of Key West’s nightlife scene.


Natural Beauty

Key West isn’t known for its beaches, but Fort Zachary Taylor Historic State Park is a great place to swim, snorkel, and catch the sunset. Explore the waters around Key West by sailboat, kayak, or sunset cruise to get a closer look at the sparkling gulf. For a unique adventure, head 70 miles offshore to Dry Tortugas National Park. Explore Fort Jefferson, the coral reefs, and the island’s impressive variety of wildlife and tropical plants.
 

Historical Markers

To get a quick look at everything Key West has to offer, hop on the Conch Tour Train. You’ll get an earful of the area’s past, along with a little local trivia. When you’re ready to dig in, make the Ernest Hemingway Home & Museum your first stop. Here you can learn more about the famous writer’s life and see where he penned some of his best selling novels.

Don't miss a tour of the Harry S. Truman Little White House, a command center during World War I and II as well as the winter home of President Harry S. Truman. Today the house is both a museum and a political retreat, and it’s well worth a visit.
 

Vibrant Nightlife

No trip to Key West is complete without a night out on the town, and options range from family-friendly to wildly theatrical. Take the family to Mallory Square, where you’ll find local performers, plenty of fried food, and gorgeous sunset views. For some grownup fun, take in a performance at Key West’s Fringe Theater, the Red Barn Theatre, or the Waterfront Playhouse. Finish the night off with a drink at the Green Parrot, Key West’s oldest bar, or Sloppy Joe’s, one of Hemingway’s favorite hangouts.

Whether you prefer culture or the outdoors, Key West has plenty to offer in a relaxed, welcoming atmosphere. One night here isn’t enough, so book a vacation home and stay awhile on this island destination.
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