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

Coconut Cabana

Key West
An Old town Key West home, located in the Historic District and just one half a block off Duval Stre...
Home 3 / 2 / 6

$380 - $540
Per Night

$2450 - $3570
Per Week

Southard Sophistication

Key West
30 DAY MINIMUM RENTAL This amazing restoration of a majestic Key West bungalow is incredible. Mo...
Home 2 / 2 / 4

Contact
Owner
Directly
For Rates

The Victoria House

Key West
THE VICTORIA HOUSE - This gracious historical property, dating from the early 20th century, was buil...
Home 5 / 6 / 12

$865 - $1776
Per Night

$5800 - $12035
Per Week

Colony Poolside

Key West
Located just a step away from Old Town area surrounded by coconut palms and blooming bougainvilleas ...
Condo 1 / 1 / 2

$190 - $250
Per Night

$1260 - $1680
Per Week

Ann Street Cottage

Key West
This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so own...
Condo 1 / 2 / 2

$190 - $250
Per Night

$1260 - $1680
Per Week

Island Spice

Key West
ISLAND SPICE -- A beautiful 2 bedroom, 2.5 bath townhome, located in the historic Foundry building o...
Condo 2 / 3 / 6

$2000 - $4060
Per Week

Beach Club #103

Key West
Unique oceanfront living sitting 65 feet from the Atlantic. Enjoy an ocean view as ocean breezes co...
Condo 2 / 2 / 4

$270 - $400
Per Night

$1820 - $2730
Per Week

Tres Gatos

Key West
TRES GATOS: Spend a month (or two) in one of Key West's most revered neighborhoods and live like a ...
Home 2 / 1 / 4

Contact
Owner
Directly
For Rates

Sunrise Suites

Key West
Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly...
Condo 2 / 2 / 6

*
Online booking available

$239 - $399
Per Night

$1673 - $2793
Per Week

Casa Marina Condo #4

Key West
30 DAY MINIMUM RENTAL A spacious one bedroom in a four condominium building in the Casa Marina Distr...
Condo 1 / 1 / 2

Contact
Owner
Directly
For Rates

Coral Garden

Key West
CORAL GARDEN: A 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock, this h...
Condo 2 / 3 / 6

$150 - $338
Per Night

$900 - $2094
Per Week

A Place in Paradise

Key West
A PLACE IN PARADISE - You will experience true Key West living when you stay in this delightful 2 ...
Condo 2 / 3 / 6

$1550 - $3444
Per Week

Ashe Splashe

Key West
30 DAY MINIMUM RENTAL From the owners of South of Frances here is another beautiful restoration of a...
Home 3 / 3 / 6

Contact
Owner
Directly
For Rates

Shipyard 106-2

Key West
Located in a very quiet corner of Truman Annex, this condo is a perfect getaway. This one bedroom an...
Condo 1 / 1 / 4

*
Online booking available

$1500 - $2100
Per Week

Lavender Jungle

Key West
LAVENDER JUNGLE - Beautiful 2 bedroom 1 bath downstairs Shipyard condo located in Truman Annex, thi...
Condo 2 / 1 / 4

$1175 - $2683
Per Week

Ann Street Tranquility

Key West
This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so own...
Condo 1 / 1 / 2

$200 - $260
Per Night

$1330 - $1750
Per Week

Duval Breeze

Key West
DUVAL BREEZE: Enjoy the great location of this beautiful 2 bedroom 2.5 bath townhome located in th...
Condo 2 / 3 / 6

$225 - $457
Per Night

$1350 - $2864
Per Week

Villa Soleil

Key West
VILLA SOLEIL -- Located in the historic Foundry building of Truman Annex, a beautiful gated communit...
Condo 2 / 3 / 6

$1650 - $3553
Per Week

Admiral's Treasure

Key West
Amazing, sophisticated home in the fabulous Truman Annex enclave. You can't beat an Admiral's Lane ...
Home 4 / 4 / 8

$5500 - $7500
Per Week

La Brisa #408E Artists Haven

Key West
30 DAY MINIMUM RENTAL La Brisa beach condominiums offer a Florida charm that is relaxing, easy a...
Condo 3 / 2 / 6

Contact
Owner
Directly
For Rates

Key Lime Pie

Key West
KEY LIME PIE - A little slice of Paradise located only one block from the Historic Seaport and clos...
Home 2 / 2 / 4

Contact
Owner
Directly
For Rates

A Suite Paradise

Key West
A SUITE PARADISE - This lovely home is truly a tropical hideaway tucked away in a secluded Key West ...
Home 2 / 2 / 6

Contact
Owner
Directly
For Rates

La Brisa #403E Ocean Vista

Key West
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for ...
Condo 2 / 2 / 4

$180 - $280
Per Night

$1190 - $1820
Per Week

Townhomes on Windsor #4

Key West
Elegance and modern sophistication are apparent as you enter any one of these six newly complete tow...
Home 3 / 3.5 / 6

$558 - $658
Per Night

$3906 - $4606
Per Week

Olivia Cottage

Key West
30 DAY MINIMUM RENTAL OLIVIA COTTAGE Recently featured in Coastal Living's "Guestbook" column, th...
Home 2 / 2.5 / 4

Contact
Owner
Directly
For Rates

 

More Getaway Locations and Properties