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Key West Vacation Rentals & House Rentals - 10 Rentals Available

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10 Vacation rentals

(123)

1 / 28

Key West Apartment

  • 2
  • 6
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly

$200

Excellent (123 reviews)

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from $200 / night

(5)

1 / 15

Key West Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly

$228

Excellent (5 reviews)

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from $228 / night

(7)

1 / 12

Key West Condo

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

$250

Very Good (7 reviews)

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from $250 / 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

(5)

1 / 14

Key West Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly

$186

Very Good (5 reviews)

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from $186 / night

(52)

1 / 36

Key West Condo

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

$209

Excellent (52 reviews)

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from $209 / night

(17)

1 / 17

Key West Townhouse

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Car not necessary

$200

Excellent (17 reviews)

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from $200 / night

(20)

1 / 22

Key West B and B

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

$730

Excellent (20 reviews)

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from $730 / 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

(2)

1 / 18

Key West Condo

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

$209

Excellent (2 reviews)

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from $209 / night

Your search has been expanded 23.1 miles to include more rentals

1 / 8

Sugarloaf House - 13.6 miles away

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

from $140 / 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
  • Pet friendly

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
  • Pet friendly

from $100 / night

1 / 19

Cudjoe Key House - 20.8 miles away

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

from $134 / night

1 / 19

Cudjoe Key House - 20.9 miles away

  • 2
  • 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

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

1 / 11

Cudjoe Key House - 20.9 miles away

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

from $127 / night

1 / 12

Cudjoe Key House - 21 miles away

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

from $100 / night

1 / 16

Cudjoe Key House - 21.1 miles away

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

from $87 / night

(2)

1 / 23

Cudjoe Key House - 21.1 miles away

  • 2
  • 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 30 mi
  • Swimming pool

$157

Very Good (2 reviews)

Inquire

from $157 / night

1 / 16

Cudjoe Key House - 21.1 miles away

  • 3
  • 5
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

from $84 / night

1 / 15

Cudjoe Key House - 21.1 miles away

  • 2
  • 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

from $70 / night

1 / 8

Cudjoe Key House - 21.1 miles away

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

from $90 / night

1 / 12

Cudjoe Key House - 21.2 miles away

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

from $97 / night

1 / 12

Summerland Key House - 22.5 miles away

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

from $164 / night

1 / 15

Summerland Key House - 22.6 miles away

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

from $117 / night

1 / 12

Summerland Key House - 22.6 miles away

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

from $84 / night

(1)

1 / 23

Summerland Key House - 22.8 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$500

Very Good (1 reviews)

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from $500 / night

1 / 24

Summerland Key House - 22.9 miles away

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

from $267 / night

1 / 12

Summerland Key House - 22.9 miles away

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

from $200 / night

1 / 13

Summerland Key House - 23 miles away

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

from $207 / night

1 / 18

Summerland Key House - 23 miles away

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

from $168 / night

1 / 14

Summerland Key House - 23.1 miles away

  • 2
  • 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

from $110 / 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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