Florida - Florida Keys Vacation Rental Getaways

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  • Property Options
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  • Bath
  • Sleeps
Max Price Per Week $
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  • Apt/Room/Suite
  • Air Conditioning
  • Washer/Dryer
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  • 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

Duval Breeze

Key West
DUVAL BREEZE: 2 bedroom 2.5 bath townhome in Duval Square. 1st floor offers an open floor plan w...
Home 2 / 2.5 / 6

$240 - $508
Per Night

$1385 - $3154
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 - $418
Per Night

$1230 - $2603
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 - $5500
Per Week

Indigo Reef Villa 60

Marathon
This spacious three bedroom, two and a half bath Villa will make you feel right at home. Each bedroo...
Villa 3 / 2.5 / 6

*
Online booking available

$375 - $1245
Per Night

$1505 - $7490
Per Week

Indigo Reef Villa 59

Marathon
This spacious three bedroom, two and a half bath Villa will make you feel right at home. Each bedroo...
Villa 3 / 2.5 / 6

*
Online booking available

$375 - $1245
Per Night

$1505 - $7490
Per Week

Sundown Refuge

Key West
SUNDOWN REFUGE: Brilliant sunshine and magnificent sunsets in the Harbour Place condo complex in Tru...
Condo 2 / 2 / 5

$330 - $711
Per Night

$2025 - $4060
Per Week

Indigo Reef Villa 34

Marathon
This spacious three bedroom, two and a half bath Villa will make you feel right at home. Each bedroo...
Villa 3 / 3 / 8

*
Online booking available

$375 - $1245
Per Night

$1505 - $7490
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

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

$3800 - $4500
Per Week

Indigo Reef Villa 30

Marathon
This spacious three bedroom, two and a half bath Villa will make you feel right at home. Each bedroo...
Villa 3 / 3 / 8

*
Online booking available

$375 - $1245
Per Night

$1505 - $7490
Per Week

Indigo Reef Villa 54

Marathon
This spacious three bedroom, two and a half bath Villa will make you feel right at home. Each bedroo...
Villa 3 / 2.5 / 6

*
Online booking available

$375 - $1245
Per Night

$1505 - $7490
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

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

$250 - $371
Per Night

$1357 - $2812
Per Week

Sunny View

Key West
SUNNY VIEW - Adorable, affordable, and a great location! You bed! Sunny View is the monthly rental K...
Cottage 1 / 2 / 2

Contact
Owner
Directly
For Rates

Coconut Cottage

Key West
COCONUT COTTAGE: The perfect escape if you’re looking to get away from it all. Located in a quiet ne...
Cottage 1 / 2 / 2

Contact
Owner
Directly
For Rates

Fan-tastic Getaway

Key West
FAN-tastic GETAWAY: Formerly owned by actress and fan dancer, Sally Rand. 60" Smart TV and sur...
Home 3 / 2.5 / 6

Contact
Owner
Directly
For Rates

Lovely home on beautiful Coco Plum Beach with 100' of dee...

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

*
Online booking available

$4000 - $6500
Per Week

Walk to Sombrero Beach

Marathon
Escape to gorgeous Marathon, Florida Keys for a romantic getaway or a fun family retreat. For famili...
Home 3 / 2 / 8

*
Online booking available

$1500 - $1900
Per Week

Truman's Hideaway

Key West
TRUMAN'S HIDEAWAY: Lovely condo in the exclusive Harbour Place condominium complex in Truman Annex. ...
Condo 2 / 2 / 5

$305 - $580
Per Night

$1900 - $3879
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

$230 - $493
Per Night

$1425 - $3241
Per Week

Quick Ocean access in Key Colony Beach

Key Colony Beach
This 2100 sq ft bright and spacious property is located just 3 houses back from the canal entrance ...
Condo 3 / 2.5 / 8

*
Online booking available

$1250 - $1700
Per Week

The Dolphin House

Key West
THE DOLPHIN HOUSE: Two houses with the comfort of one. The Dolphin House comprises a main house and ...
Home 4 / 3.5 / 8

$4650 - $10585
Per Week

Dragonfly

Key West
Dragonfly - An extraordinary home that will impress you with expansive outdoor lounging areas and sp...
Home 2 / 3.5 / 6

Contact
Owner
Directly
For Rates

Key West Ginger House

Key West
KEY WEST GINGER HOUSE: 2 bedrooms, 2 full baths ensuite. Historic home built in 1933 takes adv...
Home 2 / 2 / 6

$240 - $471
Per Night

$1400 - $2944
Per Week

Cayo Hueso Sunshine

Key West
CAYO HUESO SUNSHINE: Awaken your senses with tropical breezes, turquoise waters and Key West Sunshin...
Home 2 / 3 / 6

Contact
Owner
Directly
For Rates

 

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