Key West Beach Vacation Rentals
 
 
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Tropical Dreaming
2 bedroom Key West Home Vacation Rental Home
2 BR/ 2.50 BA Sleeps 6
More Info
The Hemingway
2 bedroom Key West Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 4
More Info
Hidden Treasure
2 bedroom Key West Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 4
More Info
 
 
 
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Bowe Conch House

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

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Cottage 3 / 2 / 6

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Owner
Directly
For Rates

 
 

Sunny View

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

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Cottage 1 / 2 / 2

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Owner
Directly
For Rates

 
 

Havana Lane: A classic conch cottage with rustic charm

Key West
Havana Lane hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch ...

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Home 2 / 2 / 4

Online Booking

$320 - $570
Per Night

$2030 - $3850
Per Week

 
 

Tranquility

Key West
TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity...

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Cottage 1 / 1.5 / 4

$215 - $418
Per Night

$1230 - $2603
Per Week

 
 

Artist Garden

Key West
Golf nearby, Ocean nearby
ARTIST GARDEN : 2 bedroom 2.5 bath located in the prestigious Admirals Lane neighborhood of Truman...

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Home 2 / 2.5 / 4

$315 - $616
Per Night

$1910 - $4118
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...

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Condo 3 / 2 / 8

Online Booking

$350 - $690
Per Night

$2310 - $4830
Per Week

 
 

Fan-tastic Getaway

Key West
FAN-tastic GETAWAY (monthly rental): This home has everything, including a bit of Key West history. ...

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Home 3 / 2.5 / 6

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Owner
Directly
For Rates

 
 

Coral Casita

Key West
Coral Casita - Weekly Vacation Rental Completely re-designed, re-decorated and ready for your isla...

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Home 3 / 3 / 8

$245 - $450
Per Night

$1380 - $2781
Per Week

 
 

Duval Square Retreat: A beautiful condo steps from the ac...

Key West
Duval Square Retreat: A beautiful condo steps from the action Duval Square - The Retreat. In the he...

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Condo 2 / 2.5 / 4

Online Booking

$300 - $550
Per Night

$1960 - $3850
Per Week

 
 

Paradise Place

Key West
Golf nearby, Ocean nearby
PARADISE PLACE: Ground level 1-bedroom 1-bath condo in the Palm Gardens community just 6 blocks f...

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Condo 1 / 1 / 4

$165 - $363
Per Night

$945 - $2313
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...

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Home 5 / 5.5 / 12

$805 - $1689
Per Night

$5350 - $11433
Per Week

 
 

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

Key West
Ocean View
Enjoy gentle ocean breezes and gorgeous views at Sea Orchid (La Brisa #405E) La Brisa beach condomi...

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Condo 2 / 2 / 4

Online Booking

$250 - $439
Per Night

$1610 - $2940
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...

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Condo 2 / 2 / 5

$315 - $580
Per Night

$1925 - $3879
Per Week

 
 

Coral Villa

Key West
Golf nearby, Ocean nearby
CORAL VILLA: A beautiful 3-bedroom townhome in the gated community of Coral Hammock. Just off U.S....

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Condo 3 / 3 / 8

$245 - $450
Per Night

$1380 - $2781
Per Week

 
 

Dragonfly

Key West
Dragonfly - An extraordinary home that will impress you with expansive outdoor lounging areas and sp...

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Home 2 / 3.5 / 6

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Owner
Directly
For Rates

 
 

Green Orchid

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

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Cottage 2 / 2.5 / 4

Contact
Owner
Directly
For Rates

 
 

Beach Club #104 - Unique oceanfront living with breathtak...

Key West
Ocean Front, Ocean View
Beach Club #104 - Unique oceanfront living with breathtaking views Unique oceanfront living only 65...

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Condo 2 / 2 / 6

Online Booking

$290 - $558
Per Night

$1890 - $3659
Per Week

 
 

Beach Club #112 - Unique Oceanfront living

Key West
Ocean Front, Ocean View
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peacef...

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Condo 2 / 2 / 5

Online Booking

$290 - $558
Per Night

$1890 - $3659
Per Week

 
 

The Hemingway

Key West
Golf nearby, Ocean nearby
THE HEMINGWAY -- A beautiful 2 bedroom 2 bath townhome located in the private, gated community of Tr...

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Condo 2 / 2 / 4

$230 - $493
Per Night

$1425 - $3241
Per Week

 
 

Linger Longer

Key West
Golf nearby, Ocean nearby
LINGER LONGER: 2 bedroom 1.5 bath townhome in Truman Annex. Master bedroom with queen bed and gue...

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Condo 2 / 1.5 / 5

$230 - $493
Per Night

$1425 - $3241
Per Week

 
 

Sundown Refuge

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

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Condo 2 / 2 / 5

$330 - $711
Per Night

$2025 - $4060
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...

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Condo 2 / 2.5 / 6

Online Booking

$300 - $550
Per Night

$1960 - $3850
Per Week

 
 

Pete's East Cottage: Cypress east cottage 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...

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Cottage 2 / 1 / 4

Online Booking

$270 - $475
Per Night

$1750 - $3150
Per Week

 
 

The Dolphin House

Key West
THE DOLPHIN HOUSE: Twice the comfort of and twice the amenities - located in the exclusive Truman An...

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Home 4 / 3.5 / 8

$4650 - $10585
Per Week

 
 

Key West Found

Key West
Golf nearby, Ocean nearby
KEY WEST FOUND: 2 bedroom, 2.5 bath townhome in the historic brick Foundry building within the Trum...

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Home 2 / 2.5 / 6

$280 - $616
Per Night

$1675 - $3901
Per Week

 
           
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