Florida - Florida Keys Vacation Rental Getaways

Select a vacation destination from the list below.
You can narrow your search by selecting specific travel dates, a price range or other search options.

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

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

$239 - $508
Per Night

$1418 - $3168
Per Week

Straight shot to the Atlantic Ocean!

Marathon
Wake up in your own sunrise paradise! Have coffee while sitting under your gazebo by the pool. Thi...
Home 3 / 4.5 / 8

*
Online booking available

$3000 - $4000
Per Week

A Little Slice Of Paradise

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

Contact
Owner
Directly
For Rates

Leeward Isle Key West Retreat

Key West
LEEWARD ISLE KEY WEST RETREAT: Small gated compound with only 13 properties, this townhome communi...
Condo 2 / 2 / 4

$265 - $508
Per Night

$1575 - $3168
Per Week

Two Bedroom

Marathon
Two Bedroom Unit Description: Our Waterfront Villas are situated right on the Gulf of Mexico and c...
Villa 2 / 2 / 6

*
Online booking available

$190 - $999
Per Night

$1330 - $6993
Per Week

Heliconia House

Key West
HELICONIA HOUSE (monthly rental): Pristine 3 bedroom private home is a true island escape. Located ...
Home 3 / 2.5 / 6

Contact
Owner
Directly
For Rates

Quick Atlantic access, dockage, pool

Marathon
Wake up in your own sunrise paradise! Have coffee while sitting under your gazebo by the pool. Thi...
Home 3 / 4.5 / 8

*
Online booking available

$3000 - $4000
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

$850 - $1180
Per Night

$5740 - $9940
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

$243 - $616
Per Night

$1485 - $3901
Per Week

2 bedroom/2 bathroom premium condo

Key West
2 bedroom/2 bathroom premium condo Unit Description: This is a 2 bed/2 bathroom condo that features...
Condo 2 / 2 / 6

*
Online booking available

$225 - $625
Per Night

$1575 - $4375
Per Week

Sip your coffee looking out to a tropical sunrise

Marathon
Picture yourself on a tropical island, half-asleep in a poolside lounge chair of your own private ho...
Home 4 / 3 / 10

*
Online booking available

$4100 - $5600
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 - $400
Per Night

$1750 - $3150
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 - $400
Per Night

$1750 - $3150
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

$707 - $1689
Per Night

$4770 - $11433
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

$144 - $363
Per Night

$842 - $2313
Per Week

Jun 9 - Aug 1   ***15% OFF WEEKLY RATES IN JULY*** Summertime and t ...

Conch Condo

Key West
CONCH CONDO -- 2-bedroom 2-bath upstairs condo features fully equipped kitchen, custom furniture, ...
Condo 2 / 2 / 4

$191 - $486
Per Night

$1148 - $3009
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

$198 - $3360
Per Night

$1229 - $2781
Per Week

Key Lime Calypso: A cottage in the heart of Bahama Village

Key West
The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the ...
Home 2 / 1 / 4

*
Online booking available

$270 - $400
Per Night

$1820 - $3900
Per Week

1 bedroom/1 bathroom premium condo

Key West
1 bedroom/1 bathroom premium condo Unit Description: This is a 1 bed/1 bathroom condo that features...
Condo 1 / 1 / 4

*
Online booking available

$175 - $429
Per Night

$1225 - $3003
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 - $650
Per Night

$2940 - $5320
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 - $2100
Per Week

Key Lime Pie

Key West
KEY LIME PIE: One block from the Historic Seaport and close enough to bike to all the sites and att...
Home 2 / 2 / 4

Contact
Owner
Directly
For Rates

Beach Club #112 - 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 - $470
Per Night

$1890 - $3640
Per Week

Tropical condo with spectacular ocean view

Key Colony Beach
14 NIGHT MINIMUM STAY Each unit is fully furnished and has two bedrooms, two bathrooms, dining area,...
Condo 2 / 2 / 4

*
Online booking available

$1200 - $1350
Per Week

 

More Getaway Locations and Properties