Key West Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

Catherine House: A charming Old Town Key West cottage

Key West
This charming Key West style cottage is just a short walk to a selection of great restaurants, art g...
Home 2 / 2 / 4

*
Online booking available

$320 - $494
Per Night

$2100 - $4200
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 - $865
Per Night

$3710 - $6489
Per Week

Bahama Dreaming

Key West
BAHAMA DREAMING: 3-bedroom Conch cottage with outdoor dining and private pool, fenced and landscap...
Home 3 / 2 / 8

$490 - $972
Per Night

$3150 - $6402
Per Week

4 Palms

Key West
4 PALMS: Located 4 palm trees from the ocean, this 2 bedroom 2 bath condominium with sleeper sofa, ...
Condo 2 / 2 / 6

$230 - $413
Per Night

$1390 - $2725
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 - $650
Per Night

$1640 - $3676
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

$270 - $418
Per Night

$1624 - $3172
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

$1230 - $2603
Per Week

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

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

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 - $827
Per Night

$3290 - $6300
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

$315 - $513
Per Night

$2023 - $3966
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

$165 - $363
Per Night

$945 - $2313
Per Week

Osprey

Key West
OSPREY COTTAGE: This cozy cottage is located in The Colony Suites, a tropical compound nestled in th...
Cottage 0 / 1 / 2

$155 - $363
Per Night

$835 - $2240
Per Week

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

$275 - $650
Per Night

$1625 - $3676
Per Week

Whitehead House: A unique two story home beside the Audub...

Key West
Whitehead House: A unique two story home beside the Audubon House Whitehead House is a unique two-s...
Home 3 / 2 / 6

*
Online booking available

$370 - $599
Per Night

$2380 - $4900
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

$245 - $3360
Per Night

$1380 - $2781
Per Week

Papaya Place

Key West
PAPAYA PLACE: 2 bedroom 2 bath condo at 1800 Atlantic Blvd. with garden view overlooking the natur...
Condo 2 / 2 / 6

$230 - $413
Per Night

$1390 - $2725
Per Week

Sundown Refuge

Key West
SUNDOWN REFUGE: Brilliant sunshine and magnificent sunsets in the Harbour Place condo complex in Tru...
Condo 2 / 2 / 5

$330 - $711
Per Night

$2025 - $4060
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

$450 - $703
Per Night

$2940 - $5480
Per Week

Southard Street Queen Conch - A Historic compound with la...

Key West
Southard Street Queen Conch - A Historic compound with large sunny pool On a lovely tree-lined resi...
Home 4 / 4 / 8

*
Online booking available

$750 - $1120
Per Night

$5040 - $8652
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

$805 - $1689
Per Night

$5350 - $11433
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 ...
Home 2 / 2.5 / 6

$240 - $508
Per Night

$1385 - $3154
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

$470 - $770
Per Night

$3150 - $6300
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 - $418
Per Night

$1624 - $3172
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

$270 - $409
Per Night

$1720 - $3245
Per Week

 

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