Florida - Florida Keys Vacation Rental Getaways

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Sort by: Type BR/BA/Sleeps Price

Straight shot to the Atlantic Ocean!

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

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

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

$4200 - $5800
Per Week

Bowe Conch House

Key West
BOWE CONCH HOUSE (monthly rental): The Bowe Conch House has evolved within the Thomas family, Conchs...
Cottage 3 / 2 / 6

$182 - $182
Per Night

$1275 - $1275
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

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

$275 - $715
Per Night

$1925 - $5005
Per Week

Waterfront 3Br w/ Private Pool, Boat Slip, Tiki Hut & Kayaks

Marathon
Escape to the Florida Keys at this newly remodeled 3BR/2BA vacation home, set along the canal in the...
Home 3 / 2 / 6

*
Online booking available

$189 - $662
Per Night

$1324 - $4634
Per Week

Poolside Paradise

Key West
POOLSIDE PARADISE (monthly rental): Poolside Paradise was built with entertaining in mind. Privacy...
Home 2 / 2 / 4

$202 - $202
Per Night

$4650 - $10585
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

$713 - $960
Per Night

$5094 - $9800
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 - $550
Per Night

$2022 - $3850
Per Week

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 / 6

*
Online booking available

Contact
Owner
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For Rates

Walk To Sombrero Beach!! 3/2 Sfh with dockage.

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 - $1800
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

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

President's Walk

Key West
PRESIDENT'S WALK: It wasn't that long ago that President Truman took casual walks in this same loca...
Home 2 / 1.5 / 4

$195 - $462
Per Night

$1365 - $3234
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

$210 - $550
Per Night

$1470 - $3850
Per Week

Shrimp Party

Key West
Shrimp Party (MONTHLY RENTAL): Key West Pinks, parties and drinks, that is the theme for this island...
Home 2 / 2 / 4

$238 - $238
Per Night

$1663 - $1663
Per Week

Special :$1500 off ! Now $5000 + fees through 06/30/18

Marathon
Brand new, state-of-the-art home in Coco Plum. Concrete construction, metal roof, three floors, four...
Home 4 / 4 / 10

*
Online booking available

$5000 - $6500
Per Week

3Br w/ Dock Access & Stunning Bay Views from Rooftop Terrace

Marathon
Mariners will find this 3BR/3BA home the perfect retreat after a day on the water. Dock your boat ne...
Villa 3 / 3 / 8

*
Online booking available

$130 - $393
Per Night

$913 - $2751
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

Lazy Gecko

Key West
LAZY GECKO (monthly rental): This 2-bedroom downstairs condo offers the best of all worlds. Enter ...
Condo 2 / 1.5 / 4

$220 - $220
Per Night

$1537 - $1537
Per Week

Waterfront 2Br w/ Expansive Views of Boot Key Harbor & Wa...

Marathon
Waterfront 2Br w/ Expansive Views of Boot Key Harbor & Walkable Location Enjoy expansive views of B...
Condo 2 / 2 / 10

*
Online booking available

$217 - $462
Per Night

$1521 - $3231
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 - $750
Per Night

$2906 - $5250
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

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

$180 - $484
Per Night

$1260 - $3388
Per Week

 

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