Florida - Florida Keys Vacation Rental Getaways

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  • Property Options
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  • Pets Allowed
  • Private Pool
  • Pool Access
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  • Smoking allowed
  • Beach Access
  • Beach Front
  • Golf on site
  • Golf nearby
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  • Ocean View
  • Lake Front
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  • Ski in/out
  • Walk to Slopes
  • Skiing nearby
 
Sort by: Type BR/BA/Sleeps Price

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 - $732
Per Night

$2275 - $4937
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

Waterfront Luxury Villa (43) with Spectacular Sunset View...

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

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

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

Key West Charming

Key West
KEY WEST CHARMING: Downstairs 2 bedroom 1 bath home in Truman Annex, a secluded gated community in ...
Condo 2 / 1 / 4

$205 - $435
Per Night

$1235 - $2828
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 - $865
Per Night

$3710 - $6489
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

$270 - $409
Per Night

$1696 - $3245
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

Indigo Reef Villa 29

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

*
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

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

Parrot Perch

Key West
PARROT PERCH: Great location and great value for a great vacation. Parrot Perch is an upstairs 2...
Condo 2 / 2 / 5

$235 - $486
Per Night

$1365 - $3009
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

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

Osprey

Key West
OSPREY COTTAGE: This cozy cottage is located in The Colony Suites, a tropical compound nestled in th...
Cottage 0 / 1 / 2

$155 - $363
Per Night

$835 - $2240
Per Week

The Palms @ Windsor Lane-Elegant w/Private Pool & Parking...

Key West
The Palms @ Windsor Lane-Elegant w/Private Pool & Parking Near Duval Welcome to The Palms @ Windsor...
Condo 3 / 3.5 / 6

*
Online booking available

$550 - $1175
Per Night

$3570 - $7000
Per Week

2 Bedrooms Apartment at The Mutiny 88337

Coral Gables
Just 5 minutes walk from the shops of CocoWalk, restaurants and entertainment, this sophisticated co...
Apartment 2 / 2 / 4

*
Online booking available

$480 - $815
Per Night

$3360 - $5705
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

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

$275 - $508
Per Night

$1600 - $3168
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 - $770
Per Night

$3150 - $6300
Per Week

3 Bedrooms Apartment at Key Largo 88544

Key Largo
Enjoy your own private paradise and have fun in the Keys! This beautiful, spacious waterfront home h...
Home 3 / 2 / 6

*
Online booking available

$325 - $580
Per Night

$2275 - $4060
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 - $1154
Per Night

$4918 - $8652
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

$320 - $494
Per Night

$2035 - $4200
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

 

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