Key West Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

Duval Square Courtyard Condo is just steps from the action

Key West
In the heart of Old Town, convenient to everything, this condo is set above a brick and tree lined c...
Condo 3 / 2 / 8

*
Online booking available

$330 - $520
Per Night

$2100 - $4340
Per Week

Casa Grande

Key West
CASA GRANDE: Located on a quaint lane steps from Duval Street with room to park 2 vehicles off-stre...
Home 5 / 5.5 / 12

$785 - $1653
Per Night

$5300 - $11310
Per Week

Havana Lane: A classic conch cottage with rustic charm

Key West
Havana Lane hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch ...
Home 2 / 2 / 4

*
Online booking available

$320 - $370
Per Night

$2030 - $3850
Per Week

Key Lime Calypso: A cottage in the heart of Bahama Village

Key West
The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the ...
Home 2 / 1 / 4

*
Online booking available

$270 - $300
Per Night

$1820 - $3500
Per Week

Wind Swept

Key West
WIND SWEPT: Imagine yourself nestled within a serene, lushly landscaped picturesque community with w...
Home 2 / 1.5 / 6

Contact
Owner
Directly
For Rates

Coral Garden

Key West
CORAL GARDEN: 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock. Fully-equ...
Home 2 / 2.5 / 6

$180 - $360
Per Night

$1050 - $2343
Per Week

Tucked away near the Southernmost Point, Louisa's Hideawa...

Key West
Tucked away near the Southernmost Point, Louisa's Hideaway is it! Tucked away near the upper end of...
Home 3 / 3 / 6

*
Online booking available

$580 - $800
Per Night

$3710 - $6300
Per Week

Parrot Perch

Key West
PARROT PERCH: Great location and great value for a great vacation. Parrot Perch is an upstairs 2...
Condo 2 / 2 / 5

$225 - $422
Per Night

$1350 - $2973
Per Week

Pete's West Cottage steps from Duval

Key West
This property has it all! The styling of the original shot gun homes of Key West restored with a bea...
Cottage 2 / 1 / 4

*
Online booking available

$270 - $330
Per Night

$1750 - $3150
Per Week

Heliconia House

Key West
HELICONIA HOUSE (monthly rental): Pristine 3 bedroom private home is a true island escape. Located ...
Home 3 / 2.5 / 6

Contact
Owner
Directly
For Rates

Beach House Condo

Key West
BEACH HOUSE CONDO: 2 bedroom 2 bath downstairs condo in the gated Shipyard Condominium area of Tru...
Condo 2 / 2 / 4

$225 - $441
Per Night

$1450 - $3118
Per Week

Boater's Beach Haven

Key West
BOATER'S BEACH HAVEN: Located midtown on Florida Bay. Take advantage of the private boat dock; b...
Condo 2 / 2 / 6

Contact
Owner
Directly
For Rates

A Little Slice Of Paradise

Key West
A SLICE OF PARADISE: Imagine yourself in a secluded, gated community steps from the golf course, min...
Home 2 / 1.5 / 6

Contact
Owner
Directly
For Rates

Premium studio condo

Key West
Premium studio condo Unit Description: This newly refurbished studio, decorated with island-inspire...
Condo 0 / 1 / 2

*
Online booking available

$129 - $359
Per Night

$903 - $2513
Per Week

Duval Square Castaway: A condo steps from the action

Key West
In the heart of Old Town, convenient to everything. These newer townhomes are in Duval Square's bric...
Condo 2 / 2.5 / 6

*
Online booking available

$250 - $380
Per Night

$1680 - $3080
Per Week

Island Wind

Key West
ISLAND WIND: When balmy breezes beckon and tropical retreats call your name, Island Wind will be jus...
Home 2 / 2 / 4

$225 - $518
Per Night

$1339 - $3118
Per Week

Perfect Pineapple

Key West
PERFECT PINEAPPLE - Long considered a sign of hospitality, the pineapple is now widely recognized as...
Home 2 / 1 / 4

Contact
Owner
Directly
For Rates

Conch Wind

Key West
CONCH WIND: Conch-style townhome in Old Town Key West nestled in a quiet, secure compound. Ope...
Condo 2 / 2 / 4

$265 - $420
Per Night

$1575 - $3118
Per Week

Beach Club #104 - Unique oceanfront living with breathtak...

Key West
Beach Club #104 - Unique oceanfront living with breathtaking views Unique oceanfront living only 65...
Condo 2 / 2 / 6

*
Online booking available

$290 - $470
Per Night

$1890 - $3290
Per Week

Bloom'n Paradise

Key West
BLOOM'N PARADISE: Private residence with 3 bedrooms and 3 bathrooms in the main house plus a pool...
Home 4 / 4 / 8

$6000 - $11600
Per Week

Paradise Place

Key West
PARADISE PLACE: Ground level 1-bedroom 1-bath condo in the Palm Gardens community just 6 blocks f...
Condo 1 / 1 / 4

$160 - $355
Per Night

$935 - $2284
Per Week

Linger Longer

Key West
LINGER LONGER: 2 bedroom 1.5 bath townhome in Truman Annex. Master bedroom with queen bed and gue...
Condo 2 / 1.5 / 5

$230 - $428
Per Night

$1425 - $3241
Per Week

Duval Square Penthouse: A large, beautiful condo steps fr...

Key West
Duval Square Penthouse: A large, beautiful condo steps from the action Beautiful four bedroom penth...
Condo 4 / 4.5 / 10

*
Online booking available

$490 - $580
Per Night

$3290 - $5670
Per Week

President's Walk is perfectly located in the Truman Annex

Key West
President?s Walk is perfectly located in the Truman Annex. A quick stroll to Duval Street and minute...
Condo 2 / 1.5 / 4

*
Online booking available

$1890 - $3150
Per Week

The Hemingway

Key West
THE HEMINGWAY -- A beautiful 2 bedroom 2 bath townhome located in the private, gated community of Tr...
Condo 2 / 2 / 4

$230 - $428
Per Night

$1425 - $3241
Per Week

 

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