Vacation Rentals & House Rentals in Key West

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NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Bicycles available Clothes dryer

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Price per night from

$1,946

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!!!

Match: Bicycles available Clothes dryer

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Price per night from

$344

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

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Bicycles available Clothes dryer

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Price per night from

$342

Match: Bicycles available Clothes dryer

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Price per night from

$911

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Clothes dryer

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Price per night from

$911

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

Key West house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Clothes dryer

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Price per night from

$165

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Price per night from

$155

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Bicycles available Clothes dryer

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Price per night from

$258

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Bicycles available Clothes dryer

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Price per night from

$344

Moveable Feast

Key West house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$430

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New Listing Family Friendly

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Clothes dryer, Bicycles available

1 of 2 filters match

Price per night from

$367

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: Clothes dryer, Bicycles available

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Price per night from

$338

Studio Blue

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Clothes dryer, Bicycles available

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Price per night from

$331

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Clothes dryer, Bicycles available

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Price per night from

$974

“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: Clothes dryer, Bicycles available

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Price per night from

$287

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Bicycles available, Clothes dryer

1 of 2 filters match

Price per night from

$179

Southernmost Beauty

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Bicycles available, Clothes dryer

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Price per night from

$267

Clean Apartment in Old Town Key West (Best Downtown Locations)

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 52 minutes

1 of 2 match: Bicycles available, Clothes dryer

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Price per night from

$384

Clean Apartment in Old Town Key West (Best Downtown Locations)

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 52 minutes

1 of 2 match: Bicycles available, Clothes dryer

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Price per night from

$384

Historic Carriage House

Key West cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Bicycles available, Clothes dryer

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Price per night from

$229

American Shoal Lighthouse Suite Duval St. and Pool

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Bicycles available, Clothes dryer

1 of 2 filters match

Price per night from

$430

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Bicycles available, Clothes dryer

1 of 2 filters match

Price per night from

$115

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Bicycles available, Clothes dryer

1 of 2 filters match

Price per night from

$174

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Bicycles available, Clothes dryer

1 of 2 filters match

Price per night from

$180

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Bicycles available, Clothes dryer

1 of 2 filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Bicycles available, Clothes dryer

1 of 2 filters match

Price per night from

$148

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Bicycles available, Clothes dryer

1 of 2 filters match

Price per night from

$93

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Bicycles available, Clothes dryer

1 of 2 filters match

Price per night from

$138

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Bicycles available, Clothes dryer

1 of 2 filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Bicycles available, Clothes dryer

1 of 2 filters match

Price per night from

$179

Sunrise at Seaside Condo 2 Bedroom

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Key West Adventure” We were two couples on our first visit to explore the keys. The condo was nice for four people. Not fancy but adequate. Could use a little updating to make it nicer. Located quite aways from Duval atreet and the action. Uber costs about $20 one way to get downtown. Too far to walk. The pool was amazing. No complaints.

Responds fast! avg. 2 hours 41 minutes

1 of 2 match: Bicycles available, Clothes dryer

1 of 2 filters match

Price per night from

$321

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!!!!

1 of 2 match: Bicycles available, Clothes dryer

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Price per night from

$133

Shipyard-1/2 Block Duval Street

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Bicycles available, Clothes dryer

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 56 minutes

1 of 2 match: Bicycles available, Clothes dryer

1 of 2 filters match

Price per night from

$201

Nature's Boutique

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Bicycles available, Clothes dryer

1 of 2 filters match

Price per night from

$229

1 of 2 match: Bicycles available, Clothes dryer

1 of 2 filters match

Price per night from

$344

Island Style, Morning Sunrises, Salty Ocean Breezes & Downtown Key West days.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Clothes dryer

1 of 2 filters match

Price per night from

$458

Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo. Fall Specials

Key West apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Bicycles available, Clothes dryer

1 of 2 filters match

Price per night from

$840

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