Siesta Key
 
 
 

A Siesta Key vacation rental is the perfect choice for travelers who want to enjoy the beauty that has made Florida one of the world's top beach destinations and to have fun in the sun. Siesta Key is an 8-mile long barrier island in the Gulf of Mexico, just off the coast Sarasota. Two bridges connect the key to the mainland, making coming and going to the nearby attractions of Sarasota a breeze.

When you rent a house or condo on Siesta Key, you will have the opportunity to enjoy a beach that was once voted the "World's Finest and Whitest." Siesta Beach, which earned this recognition, has picnic areas, restrooms, year round lifeguards, playgrounds, and more convenient amenities for your family to enjoy. Turtle Beach is a much less crowded choice and an excellent spot for finding seashells. The most secluded beach on Siesta Key is Palmer Point Beach. Popular activities enjoyed by visitors to Siesta Key include chartering boats, guided dolphin tours, parasailing, and fishing. There are many opportunities for vacationers to fish on- and off-shore and even more types of fish to catch. Imagine the stories you will be able to share if you hook a barracuda! If you feel like taking a day trip, Bush Gardens in Tampa is a just a little over an hour away. After an exciting day of thrilling roller coasters and up close views of the fascinating wildlife, you can kick back and relax and watch the waves roll in from your Siesta Key vacation home.

 
 
 
Browse the listings near Siesta Key or filter by a nearby city from the list below.

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Featured Listings
 
House Of The Sun #212Gv
2 bedroom Sarasota Condo Vacation Rental - Ocean View Condo
2 BR/ 2.00 BA Sleeps 4
More Info
House Of The Sun #406Gs
2 bedroom Sarasota Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 4
More Info
The Anna Maria Island Beac ...
2 bedroom Bradenton Beach Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 6
More Info
 
 
 
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House Of The Sun #406Gs

Sarasota
Virtual Tour Newly renovated throughout this 4th Floor Gulf Side unit boasts beautiful designer til...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

House Of The Sun #212Gv

Sarasota
Ocean View
Virtual Tour This freshly painted Gulf View unit has carpet in the living room and both bedrooms. N...

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Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

House Of The Sun #404Gs

Sarasota
Welcome to House of the Sun - Unit 404 - “your vacation home on the beach.” This unit has new kitche...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

House Of The Sun #505Gs

Sarasota
This Gulf Side unit has new tile throughout the common areas and blue carpet in the bedrooms. This ...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

House Of The Sun #207Gs

Sarasota
This Gulf Side unit has a lot of pizazz!! The unit has brand new tile in the kitchen and living area...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
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

$107 - $286
Per Night

$750 - $2000
Per Week

 
 

Excelsior 107, 2 Bedroom, 1st Floor, Heated Pools, Spa, S...

Siesta Key
Beach Access
14 day minimum stay required. With the Bay in back and the Gulf in front, our condo at Excelsior 107...

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Condo 2 / 2 / 6

Online Booking

$100 - $480
Per Night

$750 - $2600
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...

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Condo 2 / 2 / 4

Online Booking

$107 - $286
Per Night

$750 - $2000
Per Week

 
 

Siesta Dunes 8-205, 2nd Floor, Spa, Beach, Large Heated Pool

Siesta Key
Beach Access, Ocean View
Featuring beautiful wood floors, Siesta Dunes Beach 205 in Siesta Key, Florida is an ideal choice fo...

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Condo 2 / 2 / 4

Online Booking

$100 - $600
Per Night

$850 - $2754
Per Week

 
 

House Of The Sun #209Gs

Sarasota
This Gulf Side unit has a neutral color scheme of browns and tans in the living room, while the bed...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

House Of The Sun #508Gv

Sarasota
Ocean View
Come stay in this beautiful, remodeled and redecorated ocean view apartment. It truly has that light...

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Condo 2 / 2 / 6

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

Anna Maria Island Club Unit 21

Bradenton Beach
Beach Front
Spectacular, direct gulf front condo with an enviable Gulf front location, on the beach with gorgeou...

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Condo 2 / 2 / 4

Online Booking

$390 - $500
Per Night

$2730 - $3500
Per Week

 
 

River Strand 53

Bradenton
Your spacious and fully equipped vacation Condo here in Bradenton, Florida includes a refreshing com...

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Condo 2 / 2 / 4

Online Booking

$135 - $205
Per Night

$945 - $1435
Per Week

 
 

River Strand 49

Bradenton
Located inside the River Strand community, this Bradenton vacation townhome is only 20 minutes from ...

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Condo 2 / 2 / 4

Online Booking

$135 - $205
Per Night

$945 - $1435
Per Week

 
 

A Pirate's Cove at 2109 Ave C

Bradenton Beach
Absolutely adorable vintage Bradenton Beach vacation rental cottage “A Pirates Cove” will have you w...

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Cottage 2 / 1 / 6

Online Booking

$225 - $380
Per Night

$1575 - $2660
Per Week

 
 

House Of The Sun #501Gs

Sarasota
This beautiful unit was renovated in September 2010. There is porcelain tile in the common areas, li...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

The Anna Maria Island Beach Palms 5B

Bradenton Beach
Anna Maria Island is not a place where you go to the beach. When you are on Anna Maria Island you ar...

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Condo 2 / 2 / 6

Online Booking

$220 - $420
Per Night

$1540 - $2940
Per Week

 
 

House Of The Sun #306Gs

Sarasota
This Gulf Side unit is a beach paradise! This unit has new tile throughout the common areas, beige ...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

Stoneybrook Golf Club 02

Bradenton
Enjoy your golf vacation in Bradenton and don`t forget the incredible gulf coast beaches.This relaxi...

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Home 3 / 2 / 6

Online Booking

$170 - $245
Per Night

$1190 - $1715
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

$100 - $480
Per Night

$750 - $2600
Per Week

 
 

House Of The Sun #304Gs

Sarasota
Virtual Tour Freshly Painted and Ready for Relaxation!!! This Gulf Side unit is very soothing with ...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
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

$93 - $298
Per Night

$650 - $1788
Per Week

 
 

House Of The Sun #309Gv

Sarasota
Ocean View
You will feel right at home in this cozy Gulf View unit. It has new leather furniture and a 42” LCD...

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Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

Bay Tree Club 206C, 2 Bedrooms, 2nd Floor, 2 Heated Pools...

Siesta Key
Beach Access
14 day minimum stay required. Imagine waking up in the morning knowing that a quiet Siesta Key beach...

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Condo 2 / 2 / 4

Online Booking

$100 - $379
Per Night

$750 - $2273
Per Week

 
 

Sabal Harbour 17

Bradenton
This rental home is surrounded by three popular golf courses, Tara, River Strand and Stoneybrook. En...

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Home 3 / 2 / 6

Online Booking

$170 - $245
Per Night

$1190 - $1715
Per Week

 
           
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