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 #312Gv
2 bedroom Sarasota Condo Vacation Rental - Ocean View Condo
2 BR/ 2.00 BA Sleeps 6
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House Of The Sun #501Gs
2 bedroom Sarasota Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 4
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Bay Oaks B-52, 2 Bedrooms, ...
2 bedroom Siesta Key Condo Vacation Rental Condo
2 BR/ 2.50 BA Sleeps 6
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Modern Villa - Pool, Hot Tub, Water View + Golf

Sarasota
Golf on site, Lake Front, Lake View, Ocean nearby
Sarasota Private 2-Bedroom, 2-Bathrooom Contemporary Villa at Heritage Oaks Golf & Country Club • P...

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Villa 2 / 2 / 4

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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

 
 

House Of The Sun #409Gv

Sarasota
Ocean View
This Gulf View unit was recently renovated and has recently added a new sofa and chair. There is ti...

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Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

House Of The Sun #401Gs

Sarasota
This freshly painted Gulf Side unit has new berber carpet throughout the common areas and bedrooms, ...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

House Of The Sun #312Gv

Sarasota
Ocean View
This Gulf View unit has newly installed beige carpet throughout the common areas and a renovated mas...

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Condo 2 / 2 / 6

Online Booking

$289 - $289
Per Night

$1380 - $2021
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

 
 

Florida Gulf side condo steps from fishing dock Mint clean!!

Bradenton Beach
Beach Access, Golf nearby
Our new ground level, 2 bedroom cottage (2 queen beds, 1 sleeper couch) is nothing like any other be...

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Condo 2 / 1 / 4

$100 - $300
Per Night

$700 - $1900
Per Week

 
 

The Anna Maria Island Beach Breeze

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 / 1 / 6

Online Booking

$225 - $420
Per Night

$1575 - $2940
Per Week

 
 

Midnight Pass Condo #512GF

Sarasota
Beach Front
This newly remodeled Gulf Front condo has tile throughout. The unit has a modern decor, with earth t...

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Condo 2 / 2 / 4

Online Booking

$300 - $425
Per Night

$2100 - $2975
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 - $383
Per Night

$795 - $2680
Per Week

 
 

Midnight Pass Condo #214GV

Sarasota
  Enter this Gulf Front beach getaway that is decorated throughout with seashells and items from th...

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Condo 2 / 2 / 4

Online Booking

$245 - $360
Per Night

$1715 - $2520
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

$114 - $257
Per Night

$798 - $1797
Per Week

 
 

House Of The Sun #303Gs

Sarasota
Virtual Tour This Gulf Side unit has beige carpet throughout and is decorated with light shades of ...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
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 - $289
Per Night

$875 - $2025
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

$121 - $416
Per Night

$847 - $2911
Per Week

 
 

Midnight Pass Condo #311GV

Sarasota
This Gulf View unit is warm and cozy with it's nice neutral and brown decor. This unit has tile thro...

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Condo 2 / 2 / 6

Online Booking

$245 - $360
Per Night

$1715 - $2520
Per Week

 
 

Midnight Pass Condo #314GV

Sarasota
This Gulf View unit has tile throughout common areas, 2 full size sofas and a leather recliner. The ...

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Condo 2 / 2 / 4

Online Booking

$245 - $360
Per Night

$1715 - $2520
Per Week

 
 

House Of The Sun #211Gs

Sarasota
Welcoming neutral tones lend comfort and warmth to this Gulf Side unit boasting much-requested tile ...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

House Of The Sun #316Gf

Sarasota
Ocean Front
This Gulf Front unit has tile throughout the common areas, and carpet in the bedrooms. Both bathroom...

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Condo 2 / 2 / 4

Online Booking

$343 - $343
Per Night

$1693 - $2400
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

$180 - $315
Per Night

$1260 - $2205
Per Week

 
 

Midnight Pass Condo #410GV

Sarasota
This newly renovated two bedroom/two bath condo accommodates four comfortably and offers tropical dé...

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Condo 2 / 2 / 4

Online Booking

$245 - $360
Per Night

$1715 - $2520
Per Week

 
 

House Of The Sun #511Gf

Sarasota
Ocean Front
This nicely renovated Gulf Front unit is well equipped, and tastefully decorated with a tropical the...

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Condo 2 / 2 / 2

Online Booking

$343 - $343
Per Night

$1693 - $2400
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

$360 - $445
Per Night

$2520 - $3115
Per Week

 
 

Midnight Pass Condo #506GS

Sarasota
A 2 bedroom 2 bath accommodation on the 5th floor, (accessible via two outside elevators with easy a...

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Condo 2 / 2 / 4

Online Booking

$215 - $310
Per Night

$1505 - $2170
Per Week

 
 

Midnight Pass Condo #411GV

Sarasota
This Gulf View unit has tile throughout all common areas and blue carpet in the bedrooms. The color ...

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Condo 2 / 2 / 4

Online Booking

$245 - $360
Per Night

$1715 - $2520
Per Week

 
           
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