Vacation Rentals & House Rentals in Key West

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24 house rentals

Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$108

Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach

Key West townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$917

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Price per night from

$488

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

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$342

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Price per night from

$913

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$913

The Tree House Old Town 2 Bedroom MONTHLY Rental

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

“Wonderful” Close to everything! Furnishings just the best. We stayed upstairs in the 2 bedroom 1 large bath. Great wrap around porch up stairs and down. Our key Westies were welcomed which was a plus for us! Overall Stephanie has done a great job and her sister was really helpful. Planning on returning!!!!

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Price per night from

$134

Seaside Condo 2 pools. sunny, quiet, near Old Town

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 48 minutes

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Price per night from

$107

2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“We'll be back...” We found this condo to be very clean and comfortable. We enjoyed sitting at the pool as well. Paul, the caretaker, was very pleasant and most accommodating. We shared the condo with another couple for our two night stay. It was wonderful to have our privacy (2 BR/2 baths) but still be able to share the kitchen/living room area with our friends. We had a rental car so found the location easy for shopping, dining, sightseeing on other keys and, of course, Duval Street.

Match: Safe

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Price per night from

$488

Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West

Key West condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Safe

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Price per night from

$316

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$259

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Price per night from

$2,009

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Safe

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Price per night from

$345

Sweet Caroline Seaport Key West Home Rental

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Safe

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Price per night from

$314

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Safe

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Price per night from

$976

Great rentals within 20 miles that match your search

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$668

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Safe

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Price per night from

$656

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Safe

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Price per night from

$472

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Safe

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Price per night from

$525

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$445

Hyatt Sunset Harbor

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$525

Hyatt Sunset Harbor

Stock Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$523

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Safe

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Price per night from

$622

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Safe

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Price per night from

$525

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