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Key West Vacation Rentals & House Rentals - 106 Rentals Available

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106 Vacation rentals

(143)

1 / 28

Key West Apartment

  • 2
  • 5
  • min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 12 minutes

“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

$215.00

Excellent (143 reviews)

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from $215.00 / night

1 / 17

Key West Yacht

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

Responds fast! Avg. 3 hours 47 minutes

$200.00

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from $200.00 / night

(68)

Certificate of Excellence

1 / 25

Key West Condo

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 12 minutes

Certificate of Excellence

“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

$209.00

Excellent (68 reviews)

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from $209.00 / night

1 / 8

Key West House

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$536.00

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from $536.00 / night

(20)

1 / 22

Key West B and B

  • 4
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

$800.00

Excellent (20 reviews)

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from $800.00 / night

1 / 12

Key West House

  • 2
  • 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$465.00

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from $465.00 / night

(4)

1 / 11

Key West Guest house

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“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

$393.00

Excellent (4 reviews)

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from $393.00 / night

1 / 9

Key West House

  • 2
  • 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$343.00

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from $343.00 / night

1 / 11

Key West House

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$394.00

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from $394.00 / night

1 / 26

Key West House

  • 5
  • 10
  • 28 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$743.00

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from $743.00 / night

(17)

1 / 17

Key West Townhouse

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • 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

$258.00

Excellent (17 reviews)

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from $258.00 / night

1 / 16

Key West House

  • 3
  • 6
  • 30 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$284.00

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from $284.00 / night

(1)

1 / 15

Key West Apartment

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

$100.00

Excellent (1 reviews)

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from $100.00 / night

1 / 24

Key West Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$171.00

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from $171.00 / night

1 / 23

Key West House

  • 3
  • 6
  • min stay varies
  • Child friendly
  • Air conditioning

$184.00

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from $184.00 / night

(11)

1 / 24

Key West House

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$268.00

Very Good (11 reviews)

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from $268.00 / night

(1)

1 / 24

Key West House

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$275.00

Excellent (1 reviews)

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from $275.00 / night

(1)

1 / 25

Key West House

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$268.00

Excellent (1 reviews)

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from $268.00 / night

(23)

1 / 24

Key West House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$225.00

Very Good (23 reviews)

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from $225.00 / night

1 / 24

Key West House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$210.00

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from $210.00 / night

1 / 24

Key West House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$157.00

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from $157.00 / night

(2)

1 / 24

Key West House

  • 1
  • 2
  • min stay varies
  • Child friendly
  • Air conditioning

$179.00

Excellent (2 reviews)

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from $179.00 / night

(29)

1 / 24

Key West Cottage

  • 1
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$175.00

Very Good (29 reviews)

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from $175.00 / night

(1)

1 / 24

Key West House

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$190.00

Excellent (1 reviews)

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from $190.00 / night

(9)

1 / 23

Key West Apartment

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$264.00

Excellent (9 reviews)

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from $264.00 / night

(3)

1 / 24

Key West House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,001.00

Excellent (3 reviews)

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from $1,001.00 / night

(58)

1 / 24

Key West House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$325.00

Very Good (58 reviews)

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from $325.00 / night

(55)

1 / 24

Key West House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$300.00

Very Good (55 reviews)

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from $300.00 / night

1 / 24

Key West House

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$157.00

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from $157.00 / night

(4)

1 / 24

Key West House

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$210.00

Excellent (4 reviews)

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from $210.00 / night

1 / 22

Key West House

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$148.00

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from $148.00 / night

1 / 24

Key West House

  • 2
  • 4
  • min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

$197.00

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from $197.00 / night

1 / 24

Key West House

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$268.00

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from $268.00 / night

(1)

1 / 25

Key West House

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$550.00

Excellent (1 reviews)

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from $550.00 / night

(27)

1 / 24

Key West House

  • 3
  • 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$550.00

Very Good (27 reviews)

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from $550.00 / night

(3)

1 / 24

Key West Apartment

  • 1
  • 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$152.00

Excellent (3 reviews)

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from $152.00 / night

(17)

1 / 24

Key West House

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$251.00

Very Good (17 reviews)

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from $251.00 / night

(1)

1 / 24

Key West Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$166.00

Excellent (1 reviews)

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from $166.00 / night

1 / 24

Key West Apartment

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$140.00

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from $140.00 / night

(53)

1 / 28

Key West Apartment

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$186.00

Excellent (53 reviews)

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from $186.00 / 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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