Key West Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

Cayo Hueso Sunshine

Key West
CAYO HUESO SUNSHINE: 2-bedroom, den, 3-bath home. Secluded location near Smathers Beach. Kitchen is...
Home 2 / 3 / 6

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

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 - $400
Per Night

$1750 - $3150
Per Week

The Dolphin House

Key West
THE DOLPHIN HOUSE: Two houses with the comfort of one. The Dolphin House comprises a main house and ...
Home 4 / 3.5 / 8

$4650 - $10585
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

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 - $3640
Per Week

Coconut Cottage

Key West
COCONUT COTTAGE: The perfect escape if you’re looking to get away from it all. Located in a quiet ne...
Cottage 1 / 2 / 2

Contact
Owner
Directly
For Rates

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 - $531
Per Night

$1890 - $4118
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

$260 - $469
Per Night

$1625 - $3676
Per Week

May 3 - Jun 1   ***Island Wind - Tropical Winds Are Beckoning And N ...

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 - $3168
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

$290 - $470
Per Night

$1890 - $3640
Per Week

May 3 - Jun 1   SUPER SAVINGS WITH SUMMER PRICING DURING THE MONTH ...

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 - $375
Per Night

$1235 - $3153
Per Week

Ann Street Cottage: A bright and airy home near Duval Street

Key West
Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a ch...
Cottage 1 / 1.5 / 2

*
Online booking available

$240 - $360
Per Night

$1470 - $2730
Per Week

Duval Sea Turtle

Key West
DUVAL SEA TURTLE: This townhome has 2 bedrooms and 2.5 baths with a balcony off the master bedroom ...
Condo 2 / 2.5 / 6

$225 - $508
Per Night

$1350 - $3154
Per Week

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

$850 - $1180
Per Night

$5740 - $9940
Per Week

Hidden Treasure

Key West
HIDDEN TREASURE (Monthly Rental): You could easily pass by this jewel of a home without ever knowi...
Condo 2 / 2 / 4

Contact
Owner
Directly
For Rates

Duval Breeze

Key West
DUVAL BREEZE: 2 bedroom 2.5 bath townhome in Duval Square. 1st floor offers an open floor plan w...
Condo 2 / 2.5 / 6

$225 - $508
Per Night

$1350 - $3154
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 - $480
Per Night

$2030 - $3850
Per Week

Tropical Dreaming

Key West
TROPICAL DREAMING: This tropical 2-bedroom home with classic art features, hardwood floors, tall ...
Home 2 / 1 / 4

$345 - $732
Per Night

$2275 - $4937
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

Osprey

Key West
OSPREY COTTAGE: This cozy cottage is located in The Colony Suites, a tropical compound nestled in th...
Cottage 1 / 1 / 2

$150 - $363
Per Night

$825 - $2240
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 - $9125
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 - $363
Per Night

$935 - $2313
Per Week

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 - $494
Per Night

$1650 - $3901
Per Week

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 / 6

$180 - $375
Per Night

$1050 - $2343
Per Week

 

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