Key West Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

Villa Tropicale: A lush, secluded estate in the Casa Mari...

Key West
Villa Tropicale: A lush, secluded estate in the Casa Marina District Tropical seclusion best descri...
Home 4 / 4 / 8

*
Online booking available

$857 - $1300
Per Night

$5812 - $11381
Per Week

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

Key West
Casa Atlantica: A studio condo on the Atlantic shore of Key West Located just steps from the White ...
Condo 0 / 1 / 2

*
Online booking available

$199 - $289
Per Night

$1264 - $2725
Per Week

Beach Club #112 - 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

$334 - $503
Per Night

$2212 - $4168
Per Week

Upscale 3Br w/ Chef?s Kitchen, Private Pool & Central Loc...

Key West
Upscale 3Br w/ Chef?s Kitchen, Private Pool & Central Location Affectionately known as the Captain?...
Home 3 / 3 / 6

*
Online booking available

$3299 - $8232
Per Week

Tropical Dreaming

Key West
TROPICAL DREAMING: This tropical 2-bedroom home with classic art features, hardwood floors, tall ...
Home 2 / 2.5 / 6

$345 - $732
Per Night

$2275 - $4937
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

Osprey

Key West
OSPREY - This bright and colorful studio Key West rental cottage is located in the same small commun...
Cottage 0 / 1 / 2

$155 - $363
Per Night

$835 - $2240
Per Week

Bowe Conch House

Key West
BOWE CONCH HOUSE (monthly rental): The Bowe Conch House has evolved within the Thomas family, Conchs...
Cottage 3 / 2 / 6

$179 - $179
Per Night

$1250 - $1250
Per Week

Casa Grande

Key West
CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key We...
Home 5 / 5.5 / 12

$805 - $1689
Per Night

$5350 - $11443
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

$361 - $514
Per Night

$2148 - $4408
Per Week

Cayo Hueso Sunshine

Key West
CAYO HUESO SUNSHINE: Awaken your senses with tropical breezes, turquoise waters and Key West Sunshin...
Home 2 / 3 / 6

$286 - $286
Per Night

$2000 - $2000
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 - $493
Per Night

$1425 - $3241
Per Week

Key West Ginger House

Key West
KEY WEST GINGER HOUSE: 2 bedrooms, 2 full baths ensuite. Historic home built in 1933 takes adv...
Home 2 / 2 / 6

$240 - $471
Per Night

$1400 - $2944
Per Week

A Place in Paradise

Key West
A PLACE IN PARADISE - Experience Key West living in this 2 bedroom 2.5 bath Conch-Style home in Tr...
Condo 2 / 2.5 / 6

$275 - $580
Per Night

$1640 - $3676
Per Week

Pete's Cottages: Twin Cypress cottages 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...
Home 4 / 2 / 8

*
Online booking available

$533 - $785
Per Night

$3538 - $6411
Per Week

Atlantic Paradise

Key West
ATLANTIC PARADISE -- Imagine the ocean only several yards from your balcony, in a secure gated compl...
Condo 2 / 2 / 6

$230 - $413
Per Night

$1390 - $2725
Per Week

Beach Club #103 - Unique oceanfront living with breathtak...

Key West
Beach Club #103 - Unique oceanfront living with breathtaking views Unique oceanfront living only 65...
Condo 2 / 2 / 6

*
Online booking available

$334 - $503
Per Night

$2212 - $4168
Per Week

Island Wind

Key West
ISLAND WIND : Welcome to a tropical sun drenched oasis in the heart of Old Town Key West. This char...
Home 2 / 2 / 4

$275 - $573
Per Night

$1725 - $3516
Per Week

Stylish Conch Home Studio w/ Pool & Spa - Balcony Overloo...

Key West
Stylish Conch Home Studio w/ Pool & Spa - Balcony Overlooks Fleming Street A sun-drenched Key West ...
Condo 1 / 1 / 4

*
Online booking available

$132 - $283
Per Night

$1052 - $2777
Per Week

True Paradise

Key West
TRUE PARADISE: Nestled in the ever popular local residential neighborhood known as The Meadows, thi...
Condo 2 / 2 / 4

$214 - $214
Per Night

$1500 - $1500
Per Week

Conch Adventure

Key West
CONCH ADVENTURE - Nestled in a quiet corner of the Shipyard Condominiums in Truman Annex, this 2 bed...
Condo 2 / 1 / 4

$205 - $435
Per Night

$1235 - $2828
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

Villa Paradiso: A unique mid-town paradise

Key West
This mid-town Key West home is newly renovated and beautifully decorated in jewel tones of the Medit...
Home 3 / 3 / 6

*
Online booking available

$505 - $670
Per Night

$3349 - $6463
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

$289 - $428
Per Night

$1959 - $3527
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

$216 - $216
Per Night

$1514 - $1514
Per Week

 

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