Vacation Rentals & House Rentals in Key West

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109 house rentals

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Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Air conditioning Pets allowed

All filters match

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: Air conditioning Pets allowed

All filters match

Price per night from

$480

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

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Air conditioning Pets allowed

All filters match

Price per night from

$916

Key West Gulf front Home with private dock and pool.

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Air conditioning Pets allowed

All filters match

Price per night from

$481

New Listing Family Friendly

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Air conditioning Pets allowed

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: Air conditioning Pets allowed

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Price per night from

$287

Private, heated pool. Private yard.

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Air conditioning Pets allowed

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Price per night from

$172

Match: Air conditioning Pets allowed

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Price per night from

$166

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: Air conditioning 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: Air conditioning Pets allowed

All filters match

Price per night from

$107

Match: Air conditioning Pets allowed

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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: Air conditioning Pets allowed

All filters match

Price per night from

$258

Moveable Feast

Key West house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Air conditioning Pets allowed

All filters match

Price per night from

$430

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

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Air conditioning Pets allowed

All filters match

Price per night from

$377

Noah, Family Ocean Paradise

Key West house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Air conditioning Pets allowed

All filters match

Price per night from

$1,334

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

Lovely 2 bedroom, 2 bath condo at La Brisa.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$161

Comfy Family Home in a Gorgeous Gated Community

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$343

Sunshine suit (2/2 apartment)

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$524

Key West, Private Beach, Fishing Pier, Old Town, Galleon Resort

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$492

Sweet Caroline Seaport Floor 2

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$275

Alligator Reef 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, Air conditioning

1 of 2 filters match

Price per night from

$687

Sombrero Reef Lighthouse Suite Duval St. and Pool

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$430

Island Suite @ KW Vacation

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$401

Key West Lighthouse Suite Duval St. and Pool

Key West cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$401

Tortugas Harbor Lighthouse Suite Duval St. and Pool

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$430

A Change in Latitudes - TRUMAN ANNEX

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$172

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$613

Lighthouse Suites Collection Duval St. and Pool

Key West house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 20

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$2,863

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$179

Key West Suites Hotel unit 201

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$1,145

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, Air conditioning

1 of 2 filters match

Price per night from

$338

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$148

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$115

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$174

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$138

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$180

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Air conditioning

1 of 2 filters match

Price per night from

$179

Viewing 38 of 109
rentals in Key West

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