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Key West Holiday Rentals

81 Key West Holiday Rentals were found matching your criteria.


Featured
$306 - $732 /night
$1985 - $4937 /week
Tropical Dreaming

  53 reviews   Add to Favorites

Home: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States


$144 - $363 /night
$842 - $2313 /week
Paradise Place

  26 reviews   Add to Favorites

Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States


$170 - $270 /night
$1120 - $2100 /week
Enjoy soothing ocean breezes at Tropical Tranquility (La ...

  24 reviews   Add to Favorites

Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States


$174 - $435 /night
$1050 - $2828 /week
Finn Key

  29 reviews   Add to Favorites

Condo: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States


$207 - $2235 /night
$1283 - $3241 /week
The Hemingway

  24 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States


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Perfect Pineapple

  6 reviews   Add to Favorites

Home: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States


$234 - $580 /night
$1463 - $3676 /week
A Place in Paradise

  22 reviews   Add to Favorites

Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States


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Bowe Conch House

Cottage: 3 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States


$240 - $360 /night
$1470 - $2730 /week
Ann Street Cottage: A bright and airy home near Duval Street

  43 reviews   Add to Favorites

Cottage: 1 Bedroom, 1.5 Bathroom, Sleeps 2
Location: Key West, Florida, United States



$4185 - $10585 /week
The Dolphin House

  2 reviews   Add to Favorites

Home: 4 Bedroom, 3.5 Bathroom, Sleeps 8
Location: Key West, Florida, United States


$203 - $486 /night
$1215 - $3009 /week
Parrot Perch

  22 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 5
Location: Key West, Florida, United States


$239 - $508 /night
$1418 - $3168 /week
Conch Wind

  35 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States


$250 - $380 /night
$1680 - $3150 /week
Duval Square Castaway: A condo steps from the action

  14 reviews   Add to Favorites

Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States


$175 - $386 /night
$1225 - $2702 /week
1 bedroom/1 bathroom premium condo

Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States


$279 - $711 /night
$1800 - $4060 /week
Sundown Refuge

  8 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 5
Location: Key West, Florida, United States


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Directly For Rates
Sunny View

  2 reviews   Add to Favorites

Cottage: 1 Bedroom, 2 Bathroom, Sleeps 2
Location: Key West, Florida, United States


$320 - $480 /night
$2030 - $3850 /week
Havana Lane: A classic conch cottage with rustic charm

  29 reviews   Add to Favorites

Home: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States


$490 - $730 /night
$3290 - $5670 /week
Duval Square Penthouse: A large, beautiful condo steps fr...

  40 reviews   Add to Favorites

Condo: 4 Bedroom, 4.5 Bathroom, Sleeps 10
Location: Key West, Florida, United States


Contact Owner
Directly For Rates
Bogey's Retreat

Home: 2 Bedroom, 1.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States


$225 - $625 /night
$1575 - $4375 /week
2 bedroom/2 bathroom premium condo

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States


$198 - $413 /night
$1193 - $2725 /week
Papaya Place

  27 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States


$490 - $740 /night
$3290 - $6300 /week
Louisa House: A comfortable four bedroom vacation hideaway

  49 reviews   Add to Favorites

Home: 4 Bedroom, 3.5 Bathroom, Sleeps 8
Location: Key West, Florida, United States


Special Offer
$221 - $580 /night
$1381 - $3676 /week
Crowner's Jewel

  33 reviews   Add to Favorites

Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States


$270 - $400 /night
$1820 - $3900 /week
Key Lime Calypso: A cottage in the heart of Bahama Village

  36 reviews   Add to Favorites

Home: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States



$1890 - $3500 /week
President's Walk is perfectly located in the Truman Annex

  19 reviews   Add to Favorites

Condo: 2 Bedroom, 1.5 Bathroom, Sleeps 4
Location: Key West, Florida, United States


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