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

Fall Special: $1300 week + fees!! now til 12/22/17 Walk T...

Marathon
Fall Special: $1300 week + fees!! now til 12/22/17 Walk To Sombrero Beach!! Escape to gorgeous Mara...
Home 3 / 2 / 8

*
Online booking available

$1500 - $1800
Per Week

Island Wind

Key West
ISLAND WIND : Welcome to a tropical sun drenched oasis in the heart of Old Town Key West. This char...
Home 2 / 2 / 4

$275 - $573
Per Night

$1725 - $3516
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

$215 - $374
Per Night

$1230 - $2334
Per Week

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

$4080 - $8831
Per Week

1 bedroom condo at resort, near Sombrero Beach

Marathon
Newly Renovated Condo, Canal Front. Walk To Shopping, Restaurants & Golf. 1 Bedroom, 1 Bath, Sleeps...
Condo 1 / 1 / 4

*
Online booking available

$125 - $129
Per Night

$800 - $900
Per Week

Vista Fresco : Oceanside condominiums with resort-style a...

Key West
Vista Fresco : Oceanside condominiums with resort-style amenities Enjoy the resort-style amenities ...
Condo 2 / 2 / 4

*
Online booking available

$307 - $403
Per Night

$2022 - $3080
Per Week

4Br/4Ba Home w/ Waterfront Balconies, Docks, Bikes - Near...

Marathon
4Br/4Ba Home w/ Waterfront Balconies, Docks, Bikes - Near Restaurants & Bars A fisherman?s dream, t...
Home 4 / 3 / 12

*
Online booking available

$1754 - $4198
Per Week

Lovely home on beautiful Coco Plum with 100' of deep wate...

Marathon
Lovely home on beautiful Coco Plum with 100' of deep water dockage! Lovely home on beautiful Coco P...
Home 5 / 4 / 12

*
Online booking available

$4000 - $6500
Per Week

A Place in Paradise

Key West
A PLACE IN PARADISE - Experience Key West living in this 2 bedroom 2.5 bath Conch-Style home in Tr...
Condo 2 / 2.5 / 6

$275 - $650
Per Night

$1640 - $3296
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

$433 - $623
Per Night

$2906 - $4900
Per Week

Waterfront 2Br w/ 2 Balconies, 2 Docks, 7 Bikes - Near Ba...

Marathon
Waterfront 2Br w/ 2 Balconies, 2 Docks, 7 Bikes - Near Bars & Restaurants Fishing and boating are p...
Condo 2 / 1.5 / 6

*
Online booking available

$988 - $2346
Per Week

Amelia Home

Key West
AMELIA HOME - 2 bedroom 2.5 bath home with sparkling private pool only four blocks from the Atlanti...
Home 2 / 2.5 / 6

$345 - $657
Per Night

$2275 - $4427
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

$298 - $478
Per Night

$1959 - $3342
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

$271 - $584
Per Night

$1805 - $4085
Per Week

Conch Adventure

Key West
CONCH ADVENTURE - Nestled in a quiet corner of the Shipyard Condominiums in Truman Annex, this 2 bed...
Condo 2 / 1 / 4

$205 - $390
Per Night

$990 - $2535
Per Week

Canal, pool, 2 BRs and a great breezeway! Key Colony Beac...

Key Colony Beach
Canal, pool, 2 BRs and a great breezeway! Key Colony Beach, Florida Keys This second level two mast...
Home 2 / 2 / 8

*
Online booking available

$1800 - $2400
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

$244 - $403
Per Night

$1516 - $2822
Per Week

Tropical Dreaming

Key West
TROPICAL DREAMING: This tropical 2-bedroom home with classic art features, hardwood floors, tall ...
Home 2 / 2.5 / 6

$345 - $732
Per Night

$2275 - $4937
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

$406 - $632
Per Night

$2653 - $4480
Per Week

Wind Swept

Key West
WIND SWEPT: Imagine yourself nestled within a serene, lushly landscaped picturesque community with w...
Home 2 / 1.5 / 6

$159 - $159
Per Night

$1113 - $1113
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

$199 - $318
Per Night

$1264 - $2380
Per Week

Sundown Refuge

Key West
SUNDOWN REFUGE: Balmy breezes, brilliant sunshine and magnificent sunsets await you at Sundown Refug...
Condo 2 / 2 / 5

$330 - $711
Per Night

$2025 - $4060
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

$857 - $1374
Per Night

$5812 - $9940
Per Week

Panoramic view, deep water dockage

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

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

$505 - $650
Per Night

$3349 - $5320
Per Week

 

More Getaway Locations and Properties