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

Key West Crown Jewel

Key West
KEY WEST CROWN JEWEL: 2-bedroom, 2-bath, penthouse condominium with 1350 square feet of living spac...
Condo 2 / 2 / 6

$345 - $531
Per Night

$2145 - $3369
Per Week

Boater's Beach Haven

Key West
BOATER'S BEACH HAVEN: Located midtown on Florida Bay. Take advantage of the private boat dock; b...
Condo 2 / 2 / 6

Contact
Owner
Directly
For Rates

Casa de Lida with it's own beach and guest cottage!

Marathon
 LOCATION: Marathon, Marathon Area, Florida Keys, Florida, USA (Key West 50 mi, Miami 90 mi, Ft...
Home 4 / 4 / 10

*
Online booking available

$6000 - $9000
Per Week

Green Orchid

Key West
GREEN ORCHID: Situated on a narrow lane in one of the last historic Old Town neighborhood, this 2-b...
Home 2 / 2.5 / 4

Contact
Owner
Directly
For Rates

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 - $440
Per Night

$1750 - $3080
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 - $1232
Per Night

$5040 - $8400
Per Week

Mediterranean styling, oceanview, pool, dockage, hot tub

Marathon
Gorgeous, 4 bedroom, 4 full bath home, plus 1/2 bath, located on exclusive Tingler Island and near S...
Home 4 / 4.5 / 10

*
Online booking available

$4000 - $4900
Per Week

Direct and easy gulf access!

Marathon
Beautiful two bedroom, two bath home in Marathon has a fantastic Gulf view and quick, easy access t...
Home 2 / 2 / 6

*
Online booking available

$1360 - $2300
Per Week

Premium studio condo

Key West
Premium studio condo Unit Description: This newly refurbished studio, decorated with island-inspire...
Condo 0 / 1 / 2

*
Online booking available

$163 - $386
Per Night

$1141 - $2702
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 - $5500
Per Week

Ocean Pointe Suites at Key Largo

Keys
Please note these Check-in Day Requirements for this property: Nov 18 2015 - Nov 20 2015 : Wednesday...
Apartment 1 / 1 / 4

*
Online booking available

$185 - $480
Per Night

$1225 - $2625
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 - $715
Per Night

$2940 - $5320
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

$240 - $396
Per Night

$1470 - $2730
Per Week

Casa Atlantica: A one BR condo on the Atlantic shore of K...

Key West
Casa Atlantica: A one BR condo on the Atlantic shore of Key West Located just steps from the White ...
Condo 1 / 1 / 2

*
Online booking available

$200 - $319
Per Night

$1190 - $2002
Per Week

Chillin' on the dock!

Marathon
Beautiful 3 bedroom home on Flamingo Island. Panoramic view of the harbor from this porch. Downstai...
Home 3 / 3 / 8

*
Online booking available

$3000 - $4000
Per Week

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 - $814
Per Night

$3290 - $5950
Per Week

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

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 - $594
Per Night

$2380 - $4480
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 - $880
Per Night

$3710 - $6300
Per Week

Faro Blanco Resort garden view 3 bedroom condo

Marathon
Luxurious and spacious condominium at Faro Blanco Marine Resort for your dream vacation in the fabul...
Condo 3 / 2 / 8

*
Online booking available

$1100 - $1500
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 - $759
Per Night

$3150 - $5600
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 - $608
Per Night

$1575 - $4256
Per Week

Duval Square Courtyard Condo is just steps from the action

Key West
In the heart of Old Town, convenient to everything, this condo is set above a brick and tree lined c...
Condo 3 / 2 / 8

*
Online booking available

$330 - $506
Per Night

$2100 - $3640
Per Week

Beach Club #201 - 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 / 6

*
Online booking available

$290 - $517
Per Night

$1890 - $3640
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 - $440
Per Night

$1820 - $3080
Per Week

 

More Getaway Locations and Properties