Key West Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

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

$180 - $462
Per Night

$1260 - $3234
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

$175 - $495
Per Night

$1225 - $3465
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

$451 - $790
Per Night

$3218 - $6300
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

$700 - $1980
Per Night

$4900 - $13860
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

$190 - $280
Per Night

$1137 - $2450
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

$307 - $550
Per Night

$2022 - $3850
Per Week

Artist's House @ Duval Square by Rent Key West Vacations ...

Key West
Artist's House @ Duval Square by Rent Key West Vacations - Located on Duval This 2 bedroom, 2.5 bat...
Condo 2 / 2.5 / 6

*
Online booking available

$289 - $550
Per Night

$1895 - $3850
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

$794 - $1180
Per Night

$5698 - $8400
Per Week

Contemporary 4Br Tropical Oasis on Fleming w/ Private Poo...

Key West
Contemporary 4Br Tropical Oasis on Fleming w/ Private Pool & Hot Tub A fabulous Key West vacation a...
Condo 4 / 3.5 / 10

*
Online booking available

Contact
Owner
Directly
For Rates

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

$200 - $550
Per Night

$1400 - $3850
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

$253 - $420
Per Night

$1643 - $3360
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

$210 - $550
Per Night

$1470 - $3850
Per Week

A Little Slice Of Paradise

Key West
A LITLE SLICE OF PARADISE: Imagine yourself in a secluded, gated community steps from the golf cours...
Home 2 / 1.5 / 6

$157 - $157
Per Night

$1099 - $1099
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

$271 - $370
Per Night

$1706 - $2800
Per Week

Conch House in the Keys? 3Br with Stunning Backyard Pool

Key West
A memorable Key West retreat for up to six guests awaits at this lovely 3BR/2.5BA rental, one of two...
Condo 3 / 2.5 / 6

*
Online booking available

$2323 - $5772
Per Week

Secluded Luxury 4Br Casa Marina East w/ 50' Pool in reope...

Key West
Secluded Luxury 4Br Casa Marina East w/ 50' Pool in reopened Florida Keys Designed by noted histori...
Home 4 / 4.5 / 8

*
Online booking available

Contact
Owner
Directly
For Rates

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

$550 - $1320
Per Night

$3850 - $9240
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

$841 - $2470
Per Week

Coral Garden

Key West
CORAL GARDEN: A 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock, this Ke...
Home 2 / 2.5 / 6

$175 - $435
Per Night

$1225 - $3045
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

$713 - $1200
Per Night

$5094 - $9800
Per Week

Conch Republic Retreat

Key West
CONCH REPUBLIC RETREAT Conch Republic Retreat is a quintessential cigar makers shotgun style house b...
Cottage 2 / 2 / 4

$221 - $221
Per Night

$1550 - $1550
Per Week

President's Walk

Key West
PRESIDENT'S WALK: It wasn't that long ago that President Truman took casual walks in this same loca...
Home 2 / 1.5 / 4

$200 - $462
Per Night

$1400 - $3234
Per Week

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

$316 - $390
Per Night

$2085 - $4060
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

$542 - $950
Per Night

$3821 - $6650
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

$160 - $440
Per Night

$1120 - $3080
Per Week

 

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