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Key West Holiday Rentals

81 Key West Holiday Rentals were found matching your criteria.


Featured
$345 - $732 /night
$2275 - $4937 /week
Tropical Dreaming

  53 reviews   Add to Favorites

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


$265 - $420 /night
$1575 - $3118 /week
Conch Wind

  35 reviews   Add to Favorites

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


$850 - $950 /night
$5740 - $8400 /week
Villa Tropicale: A lush, secluded estate in the Casa Mari...

  22 reviews   Add to Favorites

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


$205 - $375 /night
$1235 - $2828 /week
Key West Charming

  25 reviews   Add to Favorites

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


$225 - $422 /night
$1350 - $2973 /week
Conch Condo

  11 reviews   Add to Favorites

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


$225 - $471 /night
$1350 - $3096 /week
Duval Breeze

  58 reviews   Add to Favorites

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


$180 - $260 /night
$1050 - $2100 /week
Casa Atlantica: A studio condo on the Atlantic shore of K...

  31 reviews   Add to Favorites

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


$345 - $732 /night
$2275 - $4937 /week
Amelia Home

  51 reviews   Add to Favorites

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



$4000 - $8700 /week
Easy Livin'

  1 reviews   Add to Favorites

Home: 3 Bedroom, 4 Bathroom, Sleeps 8
Location: Key West, Florida, United States


$305 - $504 /night
$1900 - $3770 /week
Truman's Hideaway

  10 reviews   Add to Favorites

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


$150 - $355 /night
$825 - $2182 /week
Osprey

  43 reviews   Add to Favorites

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


Contact Owner
Directly For Rates
Wind Swept

  2 reviews   Add to Favorites

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


$230 - $413 /night
$1390 - $2725 /week
4 Palms

  27 reviews   Add to Favorites

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


$160 - $355 /night
$935 - $2284 /week
Paradise Place

  26 reviews   Add to Favorites

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


Contact Owner
Directly For Rates
Perfect Pineapple

  6 reviews   Add to Favorites

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


Contact Owner
Directly For Rates
Bowe Conch House

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


$450 - $560 /night
$2940 - $5040 /week
Villa Paradiso: A unique mid-town paradise

  46 reviews   Add to Favorites

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


$270 - $330 /night
$1750 - $3150 /week
Pete's East Cottage: Cypress east cottage steps from Duval

  17 reviews   Add to Favorites

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


$207 - $625 /night
$1449 - $4375 /week
2 bedroom/2 bathroom premium condo

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


$330 - $520 /night
$2100 - $4340 /week
Duval Square Courtyard Condo is just steps from the action

  23 reviews   Add to Favorites

Condo: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Key West, Florida, United States


$580 - $800 /night
$3710 - $6300 /week
Tucked away near the Southernmost Point, Louisa's Hideawa...

  25 reviews   Add to Favorites

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


$220 - $432 /night
$1365 - $2828 /week
Coral Villa

  11 reviews   Add to Favorites

Condo: 3 Bedroom, 3 Bathroom, Sleeps 8
Location: Key West, Florida, United States


$785 - $1653 /night
$5300 - $11310 /week
Casa Grande

  3 reviews   Add to Favorites

Home: 5 Bedroom, 5.5 Bathroom, Sleeps 12
Location: Key West, Florida, United States


$129 - $359 /night
$903 - $2513 /week
Premium studio condo

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


$250 - $380 /night
$1680 - $3080 /week
Duval Square Castaway: A condo steps from the action

  13 reviews   Add to Favorites

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


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