Vacation Rentals & House Rentals in Key West

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99 house rentals

Studio Blue

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Bicycles available Linen provided

All filters match

Price per night from

$331

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Bicycles available Linen provided

All filters match

Price per night from

$1,954

New Listing Family Friendly

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Bicycles available Linen provided

All filters match

Price per night from

$367

“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

Match: Bicycles available Linen provided

All filters match

Price per night from

$287

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 Linen provided

All filters match

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 Linen provided

All filters match

Price per night from

$459

Match: Bicycles available Linen provided

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Price per night from

$914

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Bicycles available Linen provided

All filters match

Price per night from

$914

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

Key West house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Linen provided

All filters match

Price per night from

$166

Match: Bicycles available Linen provided

All filters match

Price per night from

$156

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Bicycles available Linen provided

All filters match

Price per night from

$259

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Bicycles available Linen provided

All filters match

Price per night from

$345

Moveable Feast

Key West house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Bicycles available Linen provided

All filters match

Price per night from

$430

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Linen provided

All filters match

Price per night from

$978

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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. 29 minutes

1 of 2 match: Linen provided, Bicycles available

1 of 2 filters match

Price per night from

$340

Key West Suites Hotel 205

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Bicycles available, Linen provided

1 of 2 filters match

Price per night from

$1,145

Truman Annex-Steps to Famous Duval Street

Key West townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Bicycles available, Linen provided

1 of 2 filters match

Price per night from

$395

Southernmost Beauty

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Bicycles available, Linen provided

1 of 2 filters match

Price per night from

$268

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, Linen provided

1 of 2 filters match

Price per night from

$230

1 of 2 match: Bicycles available, Linen provided

1 of 2 filters match

Price per night from

$859

Key West Suites Hotel unit 201

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Bicycles available, Linen provided

1 of 2 filters match

Price per night from

$1,145

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, Linen provided

1 of 2 filters match

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, Linen provided

1 of 2 filters match

Price per night from

$384

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, Linen provided

1 of 2 filters match

Price per night from

$430

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, Linen provided

1 of 2 filters match

Price per night from

$134

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, Linen provided

1 of 2 filters match

Price per night from

$230

"Little Paradise" Historic Seaport Old Town Key West

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Bicycles available, Linen provided

1 of 2 filters match

Price per night from

$494

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

Key West condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Bicycles available, Linen provided

1 of 2 filters match

Price per night from

$317

Ocean Vista

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Bicycles available, Linen provided

1 of 2 filters match

Price per night from

$202

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, Linen provided

1 of 2 filters match

Price per night from

$229

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, Linen provided

1 of 2 filters match

Price per night from

$840

Crystal blue seas, Island Breezes, Morning Sunrises & Key West Island days.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Linen provided

1 of 2 filters match

Price per night from

$478

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, Linen provided

1 of 2 filters match

Price per night from

$458

BOOK MARGARITAS IN PARADISE KEY WEST LUXURY MONTHLY CONDO BEST VALUE

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Linen provided

1 of 2 filters match

Price per night from

$382

1 of 2 match: Bicycles available, Linen provided

1 of 2 filters match

Price per night from

$344

1 of 2 match: Bicycles available, Linen provided

1 of 2 filters match

Price per night from

$489

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

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Bicycles available, Linen provided

1 of 2 filters match

Price per night from

$920

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

1 of 2 match: Bicycles available, Linen provided

1 of 2 filters match

Price per night from

$107

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