Vacation Rentals & House Rentals in Key West

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126 house rentals

Ocean View Estate with Private Pool 15 minutes from Key West

Cudjoe Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“This vacation home has everything you need.” This home has all the amenities you could possibly need inside and out. Very quiet and secure with a great covered porch where we spent much of our time (we had 7 in our group). Plenty of towels and miscellaneous supplies. It was very easy to book and communicate with the owners. They responded promptly to any questions.

Responds fast! avg. 59 minutes

Match: Climbing frame Towels provided

All filters match

Price per night from

$545

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Key West Suites Hotel 205

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$1,148

Truman Annex-Steps to Famous Duval Street

Key West townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$394

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$229

Southernmost Beauty

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$268

Hawkins Heaven

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$178

Oceanside, pet friendly, smart home with plenty of paddle equipment

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$224

Pelican Perch

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$184

Historic Carriage House

Key West cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$230

Coconuts on the Water

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$206

Key West Suites Hotel unit 201

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$1,148

New Listing Family Friendly

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$368

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

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 46 minutes

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$385

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

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 46 minutes

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$385

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$859

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: Climbing frame, Towels 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: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$134

"Little Paradise" Historic Seaport Old Town Key West

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$493

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: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$230

Acreage Multi-Million Dollar Beachfront Mansion w/ Pool & Billiards

Summerland Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$1,721

Salty Retreat

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$448

Keys Life

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$234

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

Key West condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$316

Sailfish Manor

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$384

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$345

Ocean Vista

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$201

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$976

Nature's Boutique

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$230

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: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$322

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$345

Studio Blue

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$332

BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$134

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

Key West apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$840

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$458

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

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$478

BOOK MARGARITAS IN PARADISE KEY WEST LUXURY MONTHLY CONDO BEST VALUE

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$382

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$488

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

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Climbing frame, Towels provided

1 of 2 filters match

Price per night from

$918

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