Vacation Rentals & House Rentals in Key West

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Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Fridge Pets allowed

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Price per night from

$107

Key West Island Vacation

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 8 minutes

Match: Fridge Pets allowed

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Price per night from

$478

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

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Fridge Pets allowed

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Price per night from

$913

“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: Fridge Pets allowed

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Price per night from

$286

Private, heated pool. Private yard.

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Fridge Pets allowed

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Price per night from

$172

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!!!!

Match: Fridge Pets allowed

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Price per night from

$133

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

Match: Fridge Pets allowed

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Price per night from

$106

Match: Fridge Pets allowed

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Price per night from

$154

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Fridge Pets allowed

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Price per night from

$257

Moveable Feast

Key West house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Fridge Pets allowed

All filters match

Price per night from

$428

Noah, Family Ocean Paradise

Key West house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Fridge Pets allowed

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Price per night from

$1,329

These homes match some but not all of your filters. Clear all filters

1 of 2 match: Fridge, Pets allowed

1 of 2 filters match

Price per night from

$166

Key West Gulf front Home with private dock and pool.

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Fridge, Pets allowed

1 of 2 filters match

Price per night from

$480

New Listing Family Friendly

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Fridge, Pets allowed

1 of 2 filters match

Price per night from

$365

Eleanor's Place in Key West Old Town - Dogs Ok

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Fridge, Pets allowed

1 of 2 filters match

Price per night from

$376

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Fridge

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 38 minutes

1 of 2 match: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$266

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: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$337

Historic Carriage House

Key West cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$229

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: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$383

Key West Suites Hotel unit 201

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Pets allowed, Fridge

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 46 minutes

1 of 2 match: Pets allowed, Fridge

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: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$430

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$115

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$138

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$174

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$153

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$180

1 of 2 match: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$859

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: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$229

Nature's Boutique

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$229

"Little Paradise" Historic Seaport Old Town Key West

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$490

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

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$343

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$970

Ocean Vista

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Pets allowed, Fridge

1 of 2 filters match

Price per night from

$200

Viewing 38 of 101
rentals in Key West

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