Key West Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

Crowner's Jewel

Key West
CROWNER'S JEWEL: Delightful 2 bedroom 2.5 bath Conch-style townhome in the quiet gated community o...
Condo 2 / 2.5 / 6

$255 - $466
Per Night

$1550 - $3277
Per Week

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 - $536
Per Night

$1890 - $4118
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 - $378
Per Night

$1235 - $2828
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 - $536
Per Night

$1650 - $3806
Per Week

Coral Villa

Key West
CORAL VILLA: A beautiful 3-bedroom townhome in the gated community of Coral Hammock. Just off U.S....
Condo 3 / 3 / 8

$220 - $432
Per Night

$1365 - $2828
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 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 - $2828
Per Week

Enjoy soothing ocean breezes at Tropical Tranquility (La ...

Key West
Enjoy soothing ocean breezes at Tropical Tranquility (La Brisa #302E) La Brisa beach condominiums o...
Condo 1 / 1 / 4

*
Online booking available

$170 - $270
Per Night

$1120 - $2030
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

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

$290 - $500
Per Night

$1890 - $3500
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

Sunny View

Key West
SUNNY VIEW - Adorable, affordable, and a great location! You bed! Sunny View is the monthly rental K...
Cottage 1 / 2 / 2

Contact
Owner
Directly
For Rates

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

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 - $378
Per Night

$1235 - $2828
Per Week

Fan-tastic Getaway

Key West
FAN-tastic GETAWAY: Formerly owned by actress and fan dancer, Sally Rand. 60" Smart TV and sur...
Home 3 / 2.5 / 6

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 - $471
Per Night

$1350 - $3096
Per Week

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

Green Orchid

Key West
GREEN ORCHID: Dreaming of living like a local in Key West? Dream no more. Green Orchid offers a true...
Cottage 2 / 2.5 / 4

Contact
Owner
Directly
For Rates

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

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

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

Enjoy gentle ocean breezes and gorgeous views at Sea Orch...

Key West
Enjoy gentle ocean breezes and gorgeous views at Sea Orchid (La Brisa #405E) La Brisa beach condomi...
Condo 2 / 2 / 4

*
Online booking available

$230 - $370
Per Night

$1470 - $2450
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

$180 - $260
Per Night

$1050 - $2100
Per Week

Louisa House: A comfortable four bedroom vacation hideaway

Key West
Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic be...
Home 4 / 3.5 / 8

*
Online booking available

$490 - $610
Per Night

$3290 - $6300
Per Week

Hidden Treasure

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

Contact
Owner
Directly
For Rates

 

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