Florida - Florida Keys Vacation Rental Getaways

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Sort by: Type BR/BA/Sleeps Price

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 - $580
Per Night

$1640 - $3676
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 - $670
Per Night

$3349 - $6463
Per Week

Truman's Hideaway

Key West
TRUMAN'S HIDEAWAY: It's hard to say which is more impressive, the view of Florida Bay from your priv...
Condo 2 / 2 / 5

$315 - $580
Per Night

$1925 - $3879
Per Week

2Br Waterfront Home w/ 2 Docks & 7 Bikes, Walk to Bars & ...

Marathon
2Br Waterfront Home w/ 2 Docks & 7 Bikes, Walk to Bars & Eateries Waterfront living awaits at this ...
Condo 2 / 1.5 / 6

*
Online booking available

$717 - $2008
Per Week

Now til Feb. 10, 2018 $1200 per week ! quick access to fi...

Marathon
Now til Feb. 10, 2018 $1200 per week ! quick access to fishing Looking for a nice clean and updated...
Home 2 / 2 / 4

*
Online booking available

$1200 - $2000
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

$155 - $363
Per Night

$835 - $2240
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 - $6000
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

$230 - $493
Per Night

$1425 - $3241
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

Beach Club #103 - Unique oceanfront living with breathtak...

Key West
Beach Club #103 - Unique oceanfront living with breathtaking views Unique oceanfront living only 65...
Condo 2 / 2 / 6

*
Online booking available

$334 - $503
Per Night

$2212 - $4168
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

$307 - $482
Per Night

$1805 - $4408
Per Week

Casa Grande

Key West
CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key We...
Home 5 / 5.5 / 12

$805 - $1689
Per Night

$5350 - $11443
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

$275 - $573
Per Night

$1725 - $3516
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 - $732
Per Night

$2275 - $4937
Per Week

1 BR condo at Skipjack Resort, near Sombrero Beach, Boot ...

Marathon
1 BR condo at Skipjack Resort, near Sombrero Beach, Boot Key Harbor This one bedroom updated condo ...
Condo 1 / 1 / 4

*
Online booking available

$125 - $129
Per Night

$800 - $900
Per Week

Casa de Rosalie

Key West
CASA DE ROSALIE: This classic 3-bedroom Conch home is located across the street from Bayview Park, ...
Home 3 / 2 / 8

$393 - $393
Per Night

$2750 - $2750
Per Week

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

Duval Square Penthouse: A large, beautiful condo steps fr...

Key West
Duval Square Penthouse: A large, beautiful condo steps from the action Beautiful four bedroom penth...
Condo 4 / 4.5 / 10

*
Online booking available

$578 - $915
Per Night

$3475 - $6411
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

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

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

$551 - $849
Per Night

$3664 - $6813
Per Week

A Little Slice Of Paradise

Key West
A LITLE SLICE OF PARADISE: Imagine yourself in a secluded, gated community steps from the golf cours...
Home 2 / 1.5 / 6

$154 - $154
Per Night

$1075 - $1075
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 - $309
Per Night

$1400 - $2725
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

Green Orchid

Key West
GREEN ORCHID (monthly rental): Have you been dreaming of living like a local in Key West? Your dream...
Cottage 2 / 2.5 / 4

$193 - $193
Per Night

$1350 - $1350
Per Week

 

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