Siesta Key Beach Vacation Rentals
 
 
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Jamaica Royale 91, 2 Bedro ...
2 bedroom Siesta Key Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 6
More Info
Gulf and Bay Club 305C, 2 ...
2 bedroom Siesta Key Condo Vacation Rental - Ocean View Condo
2 BR/ 2.00 BA Sleeps 6
More Info
Gulf and Bay Club 204C, 2 ...
2 bedroom Siesta Key Condo Vacation Rental - Ocean View Condo
2 BR/ 2.00 BA Sleeps 6
More Info
 
 
 
  Sort by:  Type BR/BA/Sleeps Price  
 

Gulf and Bay Club 108D, 2 Bedroom, Beach Front, Ground Fl...

Siesta Key
Beach Access, Beach Front, Ocean View
Want to get away from everyday life and enjoy a month alongside the #1 beach in the USA? Gulf and Ba...

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Condo 2 / 2 / 4

Online Booking

$125 - $304
Per Night

$875 - $2126
Per Week

 
 

Midnight Cove II 432, 2 Bedrooms, Large Heated Pool, Spa,...

Siesta Key
Beach Access
From the spacious balcony of this 3rd-floor condo, you can enjoy sun or shade, watch exotic birds vi...

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Condo 2 / 1.5 / 4

Online Booking

$114 - $306
Per Night

$795 - $2142
Per Week

 
 

Harbor Towers Yacht & Racquet 324, 1 Bedroom, Heated Pool...

Siesta Key
Beach Access
Discover the power that a change of scenery can have: steal away to this charming pied-a-terre just ...

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Condo 1 / 1 / 4

Online Booking

$107 - $244
Per Night

$750 - $1711
Per Week

 
 

Crescent Street 1138 B, 1 bedrooms, pool, pet friendly, w...

Siesta Key
Half-hidden by lush tropical foliage, Crescent Street 1138 B is paradise for anyone who longs to rel...

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Condo 1 / 1 / 4

Online Booking

$107 - $275
Per Night

$750 - $1926
Per Week

 
 

Jamaica Royale 101, 2 Bedrooms, 3 Heated Pools, Wifi, Sle...

Siesta Key
Enjoy an amazing location and luxurious accommodations! With indoor and outdoor seating, 3 heated po...

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Condo 2 / 2 / 6

Online Booking

$114 - $306
Per Night

$795 - $2142
Per Week

 
 

Our House at the Beach 222, 2 Bedroom, Heated Pool, Tenni...

Siesta Key
Lake View
There's plenty of room for everyone here at Our House. We have a split-level living/dining area, wit...

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Condo 2 / 2 / 4

Online Booking

$128 - $369
Per Night

$895 - $2583
Per Week

 
 

Bay Tree Club 106, 2 Bedrooms, 2 Heated Pools, Spa, Wifi,...

Siesta Key
Beach Access, Beach Front
Nestled on the southern tip of Siesta Key is our ground-floor condo, Bay Tree Club 106. Located in a...

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Condo 2 / 2 / 6

Online Booking

$107 - $244
Per Night

$750 - $1711
Per Week

 
 

Gulf and Bay Club 409B, 2 Bedrooms, Beach Front, Heated P...

Siesta Key
Beach Access, Ocean View
Perfect for guests looking for a rental of one month or longer, your time spent at Siesta Key Gulf a...

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Condo 2 / 2 / 4

Online Booking

$161 - $321
Per Night

$1125 - $2244
Per Week

 
 

White Sands Village 205, 2 Bedrooms, Heated Pool, Wifi, S...

Siesta Key
Beat a path to the beach every day from your own breezy lanai when you stay at this ground-floor con...

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Condo 2 / 2 / 6

Online Booking

$107 - $244
Per Night

$750 - $1711
Per Week

 
 

Gulf and Bay Club 102B, Beach Front, 2 Bedrooms, Ground F...

Siesta Key
Beach Access, Beach Front, Ocean View
Ready to spend 28 days or more in paradise? If so, Gulf & Bay Club 102B is waiting for you. This gro...

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Condo 2 / 2 / 6

Online Booking

$125 - $304
Per Night

$875 - $2126
Per Week

 
 

Palm Bay Club G46, 1 Bedroom, 40" Hdtv, Heated Pool, Wifi...

Siesta Key
Beach Access
With the top-rated beach in the country in your backyard, Palm Bay Club G46 delivers the perfect Gul...

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Condo 1 / 1 / 4

Online Booking

$107 - $275
Per Night

$750 - $1926
Per Week

 
 

Polynesian Gardens Villa P6, 2 Bedrooms, Heated Pool, Car...

Siesta Key
Welcome to your home in paradise! This standalone 2-bedroom villa offers privacy and relaxation for ...

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Condo 2 / 2 / 4

Online Booking

$94 - $214
Per Night

$657 - $1496
Per Week

 
 

Gulf and Bay Club 204C, 2 Bedroom, Beach Front, 3 Pools, ...

Siesta Key
Beach Access, Ocean View
Come vacation on the white sands of Siesta Beach! When you stay at our condo at Gulf and Bay Club 20...

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Condo 2 / 2 / 6

Online Booking

$125 - $304
Per Night

$875 - $2126
Per Week

 
 

Crescent Street 1138 A, 2 bedrooms, pool, walk to the beach

Siesta Key
When you stay at Crescent Street 1138A, you can walk to the east side of Siesta Key in just minutes ...

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Condo 2 / 1 / 6

Online Booking

$114 - $306
Per Night

$795 - $2142
Per Week

 
 

Siesta Dunes Beach 201, 2 Bedrooms, Large Heated Pool, Sp...

Siesta Key
Beach Access
This unit has been newly renovated in the fall of 2017. Stunning seaside decor, new kitchen, baths, ...

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Condo 2 / 2 / 6

Online Booking

$136 - $429
Per Night

$950 - $3002
Per Week

 
 

Casa Siesta, Ground Floor, 2 bedrooms, walk to Siesta Key...

Siesta Key
Casa Siesta makes fun in the sun so easy! The 2-bedroom, ground-floor condo is just a short walk fro...

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Condo 2 / 1 / 4

Online Booking

$107 - $244
Per Night

$750 - $1711
Per Week

 
 

Bay Oaks D-42, 2 Bedrooms, Siesta Key Florida, Updated Condo

Siesta Key
With 2 bedrooms and 2.5 bathrooms, Bay Oaks D-42 can accommodate a family of 5 or 2 couples with equ...

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Condo 2 / 2.5 / 5

Online Booking

$99 - $244
Per Night

$695 - $1711
Per Week

 
 

Crescent Street Manor, 3 Bedrooms, Walk to Beach, Private...

Siesta Key
When you stay at Crescent Street Manor, you can walk to the east side of Siesta Key in just minutes ...

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Condo 3 / 2 / 10

Online Booking

$199 - $736
Per Night

$1395 - $5155
Per Week

 
 

Jamaica Royale Tower T23, 2 Bedrooms, 3 Heated Pools, Sle...

Siesta Key
Beach Access, Ocean View
Welcome to beach living with gulf views from this breezy, comfortable condo on the shores of Siesta ...

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Condo 2 / 2 / 4

Online Booking

$171 - $613
Per Night

$1195 - $4294
Per Week

 
 

Siesta Key Excelsior 306, 3 Bedrooms, Pools, Tennis, Slee...

Siesta Key
Beach Access
With spectacular views of the beautiful trees, pond, pool and peek a boo view of the Intracoastal, y...

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Condo 3 / 2 / 6

Online Booking

$129 - $369
Per Night

$900 - $2583
Per Week

 
 

Gulf and Bay Club 305C, 2 Bedrooms, 3 pools, Gym, Spa, Wi...

Siesta Key
Beach Access, Ocean View
Roll into the lap of luxury and enjoy a unit that’s still sparkling new. Siesta Key Gulf and Bay Clu...

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Condo 2 / 2 / 6

Online Booking

$161 - $402
Per Night

$1125 - $2815
Per Week

 
 

Gulf Holidays 15, 1 Bedroom, 2nd Floor, Heated Pool, Slee...

Siesta Key
Beach Access
Budget-friendly and just a block from a beach rated #1 in the country, it’s easy to see why Gulf Hol...

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Condo 1 / 1 / 4

Online Booking

$107 - $275
Per Night

$750 - $1926
Per Week

 
 

Gulf and Bay Club: Bayside 1303-D, 2 Bedrooms, Sleeps 6, ...

Siesta Key
Ocean View
When you pull up to the Gulf and Bay Club: Bayside 1303-D you will know right away that you made the...

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Condo 2 / 2 / 6

Online Booking

$114 - $306
Per Night

$795 - $2142
Per Week

 
 

Jamaica Royale Tower T24, 2 Bedrooms, 3 Heated Pools, Sle...

Siesta Key
Beach Access, Ocean View
Fresh ocean breezes, spectacular sunsets, beautiful gulf view, and rolling waves await you at this G...

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Condo 2 / 2 / 6

Online Booking

$171 - $549
Per Night

$1195 - $3844
Per Week

 
 

Beachaven 52, 1 bedroom, Ground Floor, Pool, Sleeps 4

Siesta Key
Ocean View
Imagine this: You step out your front door, and there, at the end of a walkway flanked by shrubbery ...

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Condo 1 / 2 / 4

Online Booking

$127 - $203
Per Night

$889 - $1418
Per Week

 
           
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