Florida - Florida Keys Vacation Rental Getaways

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  • Property Options
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  • 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

$210 - $550
Per Night

$1470 - $3850
Per Week

The Hemingway

Key West
THE HEMINGWAY -- A beautiful 2 bedroom 2 bath townhome located in the private, gated community of Tr...
Condo 2 / 2 / 4

$210 - $550
Per Night

$1470 - $3850
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

$325 - $825
Per Night

$2275 - $5775
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

$210 - $300
Per Night

$1260 - $2240
Per Week

Gulfstream Dream is a 4 BR on canal and pool dream come t...

Marathon
Gulfstream Dream is a 4 BR on canal and pool dream come true! This house has everything! This home ...
Home 4 / 3 / 10

*
Online booking available

$2700 - $4000
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

$225 - $605
Per Night

$1575 - $4235
Per Week

Osprey

Key West
OSPREY - This bright and colorful studio Key West rental cottage is located in the same small commun...
Cottage 0 / 1 / 2

$125 - $385
Per Night

$875 - $2695
Per Week

Sundown Refuge

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

$300 - $748
Per Night

$2100 - $5236
Per Week

Upscale 3Br w/ Chef?s Kitchen, Private Pool & Central Loc...

Key West
Upscale 3Br w/ Chef?s Kitchen, Private Pool & Central Location Affectionately known as the Captain?...
Home 3 / 3 / 6

*
Online booking available

$293 - $720
Per Night

Coconut Cottage

Key West
COCONUT COTTAGE -- Adorable, affordable, and near all the action.... You bet! Coconut Cottage is the...
Cottage 1 / 2 / 2

$200 - $200
Per Night

$1397 - $1397
Per Week

True Paradise

Key West
TRUE PARADISE: Nestled in the ever popular local residential neighborhood known as The Meadows, thi...
Condo 2 / 2 / 4

$220 - $220
Per Night

$1537 - $1537
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

$175 - $495
Per Night

$1225 - $3465
Per Week

Gulfview escape with dockage, hot tub and plenty of parking

Marathon
Enjoy all the Keys have to offer in this quiet neighborhood location, 3 BR/2BA gulf front home! This...
Home 3 / 2 / 8

*
Online booking available

$2000 - $3000
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

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 - $1400
Per Week

Sunny View

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

$179 - $179
Per Night

$1250 - $1250
Per Week

Catherine House: A charming Old Town Key West cottage

Key West
This charming Key West style cottage is just a short walk to a selection of great restaurants, art g...
Home 2 / 2 / 4

*
Online booking available

$360 - $450
Per Night

$2450 - $4200
Per Week

Perfect Pineapple

Key West
PERFECT PINEAPPLE - Long considered a sign of hospitality, the pineapple is now widely recognized as...
Home 2 / 1 / 4

$221 - $221
Per Night

$1544 - $1544
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

$157 - $157
Per Night

$1099 - $1099
Per Week

Finn Key

Key West
FINN KEY: 2 bedroom 1 bath downstairs condo in The Shipyard section of Truman Annex, one of the most...
Condo 2 / 1 / 4

$180 - $462
Per Night

$1260 - $3234
Per Week

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

$225 - $605
Per Night

$1575 - $4235
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

$340 - $550
Per Night

$2240 - $3850
Per Week

Enjoy gentle ocean breezes and gorgeous views at Sea Orch...

Key West
Enjoy gentle ocean breezes and gorgeous views at Sea Orchid (La Brisa #405E) La Brisa beach condomi...
Condo 2 / 2 / 4

*
Online booking available

$270 - $330
Per Night

$1750 - $2170
Per Week

3 BR, pool, canal one house from open water and snapper!

Marathon
With quick, easy access to the Gulf and Atlantic Ocean, this home is perfect for fishing, snorkeling...
Home 3 / 3 / 8

*
Online booking available

$1700 - $3500
Per Week

Island Retreat 2Br Waterfront Villa w/2 Balconies & Aquam...

Marathon
Island Retreat 2Br Waterfront Villa w/2 Balconies & Aquamarine Ocean Views PROPERTY OVERVIEW Esca...
Villa 2 / 1.5 / 6

*
Online booking available

$165 - $497
Per Night

$1223 - $3482
Per Week

 

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