Siesta Key Beach Vacation Rentals
 
 
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Featured Listings
 
Beachaven 52, 1 bedroom, G ...
1 bedroom Siesta Key Condo Vacation Rental - Ocean View Condo
1 BR/ 2.00 BA Sleeps 4
More Info
Casa Siesta, Ground Floor, ...
2 bedroom Siesta Key Condo Vacation Rental Condo
2 BR/ 1.00 BA Sleeps 4
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
 
 
 
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Jamaica Royale 101, 2 Bedrooms, 3 Heated Pools, Wifi, Sle...

Siesta Key
A beach holiday doesn’t get any better when you combine good food and a great place to stay in the m...

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Condo 2 / 2 / 6

Online Booking

$99 - $314
Per Night

$556 - $2195
Per Week

 
 

Jamaica Royale Tower 24, 2 Bedrooms, 3 Heated Pools, Slee...

Siesta Key
Beach Access, Ocean View
Enjoy sunset views and warm Gulf breezes from the balcony of this 2 bedroom 2 bath Tower unit 24. I...

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Condo 2 / 2 / 6

Online Booking

$171 - $459
Per Night

$1195 - $2777
Per Week

 
 

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

Siesta Key
Beach Access
Decked in pure tropical style, Siesta Dunes Beach 201 in Siesta Key, Florida is an ideal choice for ...

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Condo 2 / 2 / 6

Online Booking

$114 - $371
Per Night

$636 - $2594
Per Week

 
 

Casa de Mariposa 5542, 3 Bedroom, Gulfview, Elevator, Hea...

Siesta Key
Beach Access, Ocean View
Casa de Mariposa 5542 is a beautifully designed 3 bedroom, 3 bathroom home with a gulf view, shared ...

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Home 3 / 3 / 8

Online Booking

$267 - $814
Per Night

$1780 - $4860
Per Week

 
 

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

Siesta Key
Beach Access
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

$78 - $300
Per Night

$520 - $2099
Per Week

 
 

Casa de Mariposa Mansion, 6 Bedroom, Gulf View, Heated Po...

Siesta Key
Beach Access, Ocean View
Welcome to your Island getaway at Casa de Mariposa, a beautifully designed 6 bedroom, 6 bathroom man...

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Home 6 / 6 / 16

Online Booking

$540 - $1214
Per Night

$4000 - $8500
Per Week

 
 

Casa de Mariposa 5540, 3 Bedroom, Gulfview, Elevator, Hea...

Siesta Key
Beach Access, Ocean View
Casa de Mariposa is a beautifully designed 3 bedroom, 3 bathroom home with southern exposure, a heat...

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Home 3 / 3 / 8

Online Booking

$240 - $770
Per Night

$1600 - $4590
Per Week

 
 

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

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

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Condo 2 / 2 / 4

Online Booking

$90 - $286
Per Night

$630 - $2000
Per Week

 
 

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

Siesta Key
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

$95 - $371
Per Night

$636 - $2594
Per Week

 
 

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

Siesta Key
Looking for a home away from home as you embark upon your upcoming vacation, Polynesian Gardens Vill...

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Condo 2 / 2 / 4

Online Booking

$79 - $330
Per Night

$550 - $1997
Per Week

 
 

Twin Palms 5, 1 Bedroom, Ground Floor, Heated Pool, Wifi,...

Siesta Key
You’ll be just a one-block walk from Siesta Key, the #1 rated beach in the USA when you stay at Twin...

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Condo 1 / 1 / 4

Online Booking

$83 - $333
Per Night

$556 - $2195
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

$125 - $304
Per Night

$875 - $2125
Per Week

 
 

Jamaica Royale Tower 23, 2 Bedrooms, 3 Heated Pools, Slee...

Siesta Key
Beach Access, Ocean View
Enjoy sunset views and warm Gulf breezes from the balcony of this 2 bedroom 2 bath Tower unit 24. I...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 4

Online Booking

$171 - $459
Per Night

$1195 - $2777
Per Week

 
 

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

Siesta Key
Enjoy the simple pleasures of life by doing anything and everything that you could possibly care to ...

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Condo 2 / 2.5 / 5

Online Booking

$83 - $333
Per Night

$556 - $2195
Per Week

 
 

Siesta Dunes Beach 38A, 2 Bedrooms, Ground Floor, Heated ...

Siesta Key
Do you have children who’ll delight in the geckos and insects they can discover in the garden? Or do...

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Condo 2 / 2 / 6

Online Booking

$99 - $439
Per Night

$556 - $2195
Per Week

 
 

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

Siesta Key
Beach Access, Beach Front, Ocean View
Love sunsets? How about white sand, plush beds, a choice of three pools, swans ... and a little shuf...

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Condo 2 / 2 / 6

Online Booking

$125 - $304
Per Night

$875 - $2125
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

$59 - $242
Per Night

$396 - $1695
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 & Bay Club ...

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Condo 2 / 2 / 6

Online Booking

$107 - $286
Per Night

$750 - $2000
Per Week

 
 

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

Siesta Key
Beach Access, Beach Front, Ocean View
Love sunsets? How about white sand, plush beds, a choice of three pools, swans ... and a little shuf...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 4

Online Booking

$107 - $286
Per Night

$750 - $2000
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 - $280
Per Night

$720 - $1820
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

$83 - $439
Per Night

$556 - $2195
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

$66 - $196
Per Night

$462 - $1375
Per Week

 
 

Gulf and Bay Club: Bayside 1226, 2 Bedrooms, Sleeps 6, 2 ...

Siesta Key
Beach Access, Ocean View
Just steps from the bay, our newly remodeled condo in a gated Key West-style community is the perfec...

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Condo 2 / 2 / 6

Online Booking

$83 - $333
Per Night

$556 - $2195
Per Week

 
 

Bay Oaks B-52, 2 Bedrooms, Updated Condo, Sleeps 6

Siesta Key
Beach Access
Featured on HGTV's Beachfront Bargain Hunt TV show! With views over a sunny, peek a boo view of the ...

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Condo 2 / 2.5 / 6

Online Booking

$99 - $333
Per Night

$556 - $2195
Per Week

 
 

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

Siesta Key
Beach Access
Harbor Towers 324 is a cozy 1 bedroom/ 1 bath Siesta Key condo that sleeps 2-4. Guests will feel rig...

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Condo 1 / 1 / 4

Online Booking

$78 - $300
Per Night

$520 - $2099
Per Week

 
           
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