Vacation Rentals & House Rentals in Key West

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27 house rentals

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Bicycles available Sea view

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Price per night from

$1,939

Match: Bicycles available Sea view

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Price per night from

$907

SEAPORT SERENITY in Old Town—Beach-Pool-BBQ-Hot Tub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Sea view

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Price per night from

$907

SEAPORT SAILING—Beach-Pool-BBQ-55”TV-HotTub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Sea view

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Price per night from

$970

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One-bedroom time share suite in the heart of Old Key West

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 26 minutes

1 of 2 match: Sea view, Bicycles available

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Price per night from

$337

New Listing Family Friendly

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Sea view, Bicycles available

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Price per night from

$365

Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Sea view, Bicycles available

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Price per night from

$343

Studio Blue

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Sea view, Bicycles available

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Price per night from

$330

“Fantastic Stay!” My husband and two sons (21 & 24) stayed in this condo over Christmas. This was our first stay in Key West and we wanted to be close to everything, but yet not right on Duval St. This location was perfect; literally a stones throw away from Duval St. The unit inside was decorated very lovely and had all the amenities one would need. I found the owners were nice to do business with, especially Deb who I mostly communicated with. My family and I enjoyed our stay in Key West immensely, we had so much fun! We met many very friendly people out and about town. We would love to visit again, if we do, we would like to stay in this condo or the Bella Vita, the owner's other condo.

Responds fast! avg. 14 minutes

1 of 2 match: Sea view, Bicycles available

1 of 2 filters match

Price per night from

$286

Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home.

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Sea view, Bicycles available

1 of 2 filters match

Price per night from

$257

KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Sea view, Bicycles available

1 of 2 filters match

Price per night from

$340

1 of 2 match: Sea view, Bicycles available

1 of 2 filters match

Price per night from

$154

Moveable Feast

Key West house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Sea view, Bicycles available

1 of 2 filters match

Price per night from

$428

Tee by the Sea - Luxury 2/2 1/2, WIFI, pool, parking, Bikes, 3 night min.

Key West townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Absolutely Perfect!!!” I chose this place to rent because it looked nice and it was affordable. I knew going in that it was not located on the Key West island, which was fine considering the condo came with bikes you could ride onto the island...What I experienced during my stay here is nothing short of Perfect!!! The entire condo was clean and spacious, everything inside the condo worked, the beds and all furniture were clean and comfortable, plenty of towels and linens, the showers, water presure and plumbing were excellent, the pool was clean, relaxing and private, the nights were quiet for sleeping and the gated community within the condo were friendly and fun. The bikes were the best part...10-15 minutes and you were on Duval Street, or the Southernmost Point, or Fort Zachery beach with no hassles what so ever, and I got some good exercise!!! I will definately stay here again!!!

1 of 2 match: Sea view, Bicycles available

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Price per night from

$343

Single Family Home, 3 Bedroom, 2 Baths, and Pool. Great Value!

Key West house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Sea view, Bicycles available

1 of 2 filters match

Price per night from

$165

Shipyard-1/2 Block Duval Street

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Bicycles available, Sea view

1 of 2 filters match

Price per night from

$229

Ocean Vista

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Bicycles available, Sea view

1 of 2 filters match

Price per night from

$200

Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Bicycles available, Sea view

1 of 2 filters match

Price per night from

$913

Noah, Family Ocean Paradise

Key West house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Bicycles available, Sea view

1 of 2 filters match

Price per night from

$1,329

Great rentals within 20 miles that match your search

Match: Bicycles available Sea view

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Price per night from

$262

Cassie's Paradise

Sugarloaf Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Bicycles available Sea view

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Price per night from

$5,699

Hyatt Sunset Harbor

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Sea view

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Price per night from

$510

Hyatt Sunset Harbor

Stock Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Bicycles available Sea view

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Price per night from

$523

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Sea view

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Price per night from

$482

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Sea view

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Price per night from

$445

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Sea view

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Price per night from

$471

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Sea view

All filters match

Price per night from

$525

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