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Key West Holiday Rentals

76 Key West Holiday Rentals were found matching your criteria.


Featured
$188 - $288 /night
$1200 - $1800 /week
La Dolce Vita, Steps to Duval! 3 blks to South Beach!

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


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

  54 reviews   Add to Favorites

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


$300 - $300 /night
Condo 2 br, Ocean view from Balcony

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


$230 - $493 /night
$1425 - $3241 /week
Linger Longer

  23 reviews   Add to Favorites

Condo: 2 Bedroom, 1.5 Bathroom, Sleeps 5
Location: Key West, Florida, United States


$235 - $486 /night
$1365 - $3009 /week
Conch Condo

  13 reviews   Add to Favorites

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



$4080 - $8831 /week
Easy Livin'

  1 reviews   Add to Favorites

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


$275 - $508 /night
$1600 - $3168 /week
Island Wind

  2 reviews   Add to Favorites

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


$275 - $508 /night
$1600 - $3168 /week
Leeward Isle Key West Retreat

  39 reviews   Add to Favorites

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


$470 - $900 /night
$3150 - $6300 /week
Pete's Cottages: Twin Cypress cottages steps from Duval

  34 reviews   Add to Favorites

Home: 4 Bedroom, 2 Bathroom, Sleeps 8
Location: Key West, Florida, United States


$290 - $558 /night
$1890 - $3659 /week
Beach Club #112 - Unique Oceanfront living

  10 reviews   Add to Favorites

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


$580 - $900 /night
$3710 - $6300 /week
Tucked away near the Southernmost Point, Louisa's Hideawa...

  34 reviews   Add to Favorites

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


$205 - $435 /night
$1235 - $2828 /week
Key West Charming

  26 reviews   Add to Favorites

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


$270 - $475 /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


$320 - $570 /night
$2030 - $3850 /week
Havana Lane: A classic conch cottage with rustic charm

  35 reviews   Add to Favorites

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


$275 - $650 /night
$1640 - $3676 /week
Crowner's Jewel

  33 reviews   Add to Favorites

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


Contact Owner
Directly For Rates
Cayo Hueso Sunshine

  1 reviews   Add to Favorites

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


$230 - $493 /night
$1425 - $3241 /week
The Hemingway

  26 reviews   Add to Favorites

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


$850 - $1402 /night
$5740 - $9940 /week
Villa Tropicale: A lush, secluded estate in the Casa Mari...

  25 reviews   Add to Favorites

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


$165 - $363 /night
$945 - $2313 /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
Bowe Conch House

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



$1750 - $3500 /week
President's Walk is perfectly located in the Truman Annex

  20 reviews   Add to Favorites

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


$245 - $450 /night
$1380 - $2781 /week
Coral Villa

  11 reviews   Add to Favorites

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


$270 - $475 /night
$1680 - $3080 /week
Vista Fresco : Oceanside condominiums with resort-style a...

  20 reviews   Add to Favorites

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


Contact Owner
Directly For Rates
Dragonfly

Home: 2 Bedroom, 3.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States



$4650 - $10585 /week
The Dolphin House

  2 reviews   Add to Favorites

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


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