Key West Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

Artist Garden

Key West
ARTIST GARDEN : 2 bedroom 2.5 bath located in the prestigious Admirals Lane neighborhood of Truman...
Home 2 / 2.5 / 5

$295 - $616
Per Night

$1890 - $4118
Per Week

Casa Atlantica: A one BR condo on the Atlantic shore of K...

Key West
Casa Atlantica: A one BR condo on the Atlantic shore of Key West Located just steps from the White ...
Condo 1 / 1 / 2

*
Online booking available

$190 - $304
Per Night

$1131 - $2590
Per Week

Key West Charming

Key West
KEY WEST CHARMING: Downstairs 2 bedroom 1 bath home in Truman Annex, a secluded gated community in ...
Condo 2 / 1 / 4

$205 - $435
Per Night

$1235 - $2828
Per Week

Amelia Home

Key West
AMELIA HOME - 2 bedroom 2.5 bath home with sparkling private pool only four blocks from the Atlanti...
Home 2 / 2.5 / 6

$340 - $732
Per Night

$2205 - $4937
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

$265 - $508
Per Night

$1575 - $3168
Per Week

Easy Livin'

Key West
EASY LIVIN' : Private home with pool in Truman Annex, a gated community in historic Old Town, in ...
Home 3 / 4 / 8

$4000 - $8831
Per Week

Pete's East Cottage: Cypress east 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

$257 - $428
Per Night

$1663 - $3080
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

$460 - $770
Per Night

$3080 - $5600
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 - $508
Per Night

$1450 - $3154
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 - $1689
Per Night

$5300 - $11433
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

$238 - $418
Per Night

$1596 - $3150
Per Week

Finn Key

Key West
FINN KEY: 2 bedroom 1 bath downstairs condo in The Shipyard section of Truman Annex, one of the most...
Condo 2 / 1 / 4

$205 - $435
Per Night

$1235 - $2828
Per Week

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

Truman's Hideaway

Key West
TRUMAN'S HIDEAWAY: Lovely condo in the exclusive Harbour Place condominium complex in Truman Annex. ...
Condo 2 / 2 / 5

$305 - $580
Per Night

$1900 - $3879
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

Bowe Conch House

Key West
BOWE CONCH HOUSE: The Bowe Conch House has evolved within the Thomas family, Conchs, born and raised...
Cottage 3 / 2 / 6

Contact
Owner
Directly
For Rates

Sep 8 - Oct 31   DRAGONFLY **FALL IN TO 20% OFF RENTAL RATES FOR THE ...

Dragonfly

Key West
Dragonfly - An extraordinary home that will impress you with expansive outdoor lounging areas and sp...
Home 2 / 3.5 / 6

Contact
Owner
Directly
For Rates

Key West Found

Key West
KEY WEST FOUND: 2 bedroom, 2.5 bath townhome in the historic brick Foundry building within the Trum...
Home 2 / 2.5 / 6

$270 - $616
Per Night

$1650 - $3901
Per Week

Tranquility

Key West
TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity...
Cottage 1 / 1.5 / 4

$215 - $418
Per Night

$1225 - $2603
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 - $493
Per Night

$1425 - $3241
Per Week

Lavender Jungle

Key West
LAVENDER JUNGLE: 2 bedroom 1 bath downstairs Shipyard condo located in Truman Annex. Renovated ki...
Condo 2 / 1 / 4

$205 - $435
Per Night

$1235 - $2828
Per Week

Beach Club #204 - Unique Oceanfront living

Key West
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peacef...
Condo 2 / 2 / 5

*
Online booking available

$276 - $530
Per Night

$1796 - $3920
Per Week

Coral Casita

Key West
Coral Casita - Weekly Vacation Rental Completely Re-Designed, Re-Decorated and Ready for your islan...
Home 3 / 3 / 8

$220 - $3360
Per Night

$1365 - $2781
Per Week

Conch Condo

Key West
CONCH CONDO -- 2-bedroom 2-bath upstairs condo features fully equipped kitchen, custom furniture, ...
Condo 2 / 2 / 4

$225 - $486
Per Night

$1350 - $3009
Per Week

 

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