Key West Vacation Rental Getaways


Refine Your Search
Check-In 
calendar

Check-Out
calendar
  • Property Options
  • Amenities
  • Location Type
  • Bed
  • Bath
  • Sleeps
Max Price Per Week $
  • Special Offers
  • Online Booking
  • Home/Villa
  • Cottage/Cabin
  • Condo/Townhome
  • Bed & Breakfast
  • Apt/Room/Suite
  • Air Conditioning
  • Washer/Dryer
  • Full Kitchen
  • Satellite/Cable TV
  • Handicap Access
  • High Speed Internet
  • Elevator
  • Maid Service
  • Garage Parking
  • Pets Allowed
  • Private Pool
  • Pool Access
  • Hot Tub
  • Fireplace
  • Smoking allowed
  • Beach Access
  • Beach Front
  • Golf on site
  • Golf nearby
  • Ocean Front
  • Ocean View
  • Lake Front
  • Lake View
  • Ski in/out
  • Walk to Slopes
  • Skiing nearby
 
Sort by: Type BR/BA/Sleeps Price

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 - $375
Per Night

$1225 - $2625
Per Week

Beach House Condo

Key West
BEACH HOUSE CONDO: 2 bedroom 2 bath downstairs condo in the gated Shipyard Condominium area of Tru...
Condo 2 / 2 / 4

$210 - $1160
Per Night

$1470 - $8120
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 - $925
Per Night

$1120 - $6475
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

$350 - $410
Per Night

$2310 - $2800
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

$340 - $550
Per Night

$2240 - $3850
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 - $2000
Per Night

$4900 - $14000
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 - $1040
Per Night

$1225 - $7280
Per Week

Conch Wind

Key West
CONCH WIND: Conch-style townhome in Old Town Key West nestled in a quiet, secure compound. Ope...
Condo 2 / 2 / 4

$225 - $600
Per Night

$1575 - $4200
Per Week

Emma's Secret

Key West
Emma's Secret (Monthly Rental) Located in one of Key West’s historic and most cultural neighborhoo...
Condo 2 / 1 / 4

$165 - $165
Per Night

$1156 - $1156
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

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

$170 - $170
Per Night

$1187 - $1187
Per Week

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

$270 - $330
Per Night

$1750 - $2170
Per Week

Coconut Cottage

Key West
COCONUT COTTAGE -- Adorable, affordable, and near all the action.... You bet! Coconut Cottage is the...
Cottage 1 / 2 / 2

$200 - $200
Per Night

$1397 - $1397
Per Week

Stunning Old Town 3Br w/ Private Elevator, 5 Balconies & ...

Key West
Stunning Old Town 3Br w/ Private Elevator, 5 Balconies & Community Pool PROPERTY OVERVIEW Situated...
Villa 3 / 3.5 / 6

*
Online booking available

$433 - $981
Per Night

$3031 - $6869
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

$600 - $950
Per Night

$3990 - $6650
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

$360 - $450
Per Night

$2310 - $4200
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

$300 - $389
Per Night

$1796 - $2660
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

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

$210 - $300
Per Night

$1260 - $2240
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

$340 - $550
Per Night

$2240 - $3850
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

$600 - $721
Per Night

$3990 - $6300
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

$790 - $1221
Per Night

$5320 - $8400
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

$195 - $525
Per Night

$1365 - $3675
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 - $450
Per Night

$1715 - $3150
Per Week

Parrot Perch

Key West
PARROT PERCH: Great location and great value for a great vacation. Parrot Perch is an upstairs 2...
Condo 2 / 2 / 5

$200 - $510
Per Night

$1400 - $3570
Per Week

 

More Getaway Locations and Properties