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 #305Gs
2 bedroom Sarasota Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 6
More Info
House Of The Sun #512Gf
2 bedroom Sarasota Condo Vacation Rental - Ocean Front Condo
2 BR/ 2.00 BA Sleeps 4
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Gulf Holidays 15, 1 Bedroo ...
1 bedroom Siesta Key Condo Vacation Rental Condo
1 BR/ 1.00 BA Sleeps 4
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House Of The Sun #305Gs

Sarasota
Virtual Tour This Gulf Side unit has a slight view of the water, but a beautiful view of the palm t...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

House Of The Sun #512Gf

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

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Condo 2 / 2 / 4

Online Booking

$343 - $343
Per Night

$1693 - $2400
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

 
Jan 20 - Feb 17   Book during this period today and save $50!
 

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

 
 

House Of The Sun #405Gs

Sarasota
Virtual Tour This Gulf Side unit will make you feel right at home at the beach with it's sand &...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

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 #205Gs

Sarasota
This Gulf Side unit has teal-blue carpet in the living room and bedrooms and tile in the foyer and h...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

River Strand 42

Bradenton
A beautiful 3 bedroom, 2 bathroom home with a huge screened lanai and pool (with the option of heat)...

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Home 3 / 2 / 6

Online Booking

$170 - $220
Per Night

$1190 - $1540
Per Week

 
 

House Of The Sun #208Gs

Sarasota
Virtual Tour All NEW! Totally renovated from ceiling to tile floor and everything in between! Sunny...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

Anna Maria Island Retreat

Bradenton Beach
The Anna Maria Island Retreat is a gorgeous two bedroom, two bathroom condo sleeping six. The Anna ...

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Condo 2 / 2 / 6

Online Booking

$200 - $265
Per Night

$1400 - $1855
Per Week

 
 

Anna Maria Island Beach Sands

Bradenton Beach
Beach Access
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 / 5

Online Booking

$205 - $440
Per Night

$1435 - $3080
Per Week

 
 

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

 
 

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 #504Gs

Sarasota
This Gulf Side unit has been recently renovated with tile throughout the common areas and contempora...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

The Anna Maria Island Beach Castle

Bradenton Beach
The Beach Castle is located with-in walking distance of Anna Maria Island's best waterfront restaura...

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Condo 2 / 2 / 6

Online Booking

$180 - $420
Per Night

$1260 - $2940
Per Week

 
 

House Of The Sun #413Gf

Sarasota
Ocean Front
This Gulf Front unit has beige tile in the common areas and beige carpet in the bedrooms. The color ...

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Condo 2 / 2 / 6

Online Booking

$343 - $343
Per Night

$1693 - $2400
Per Week

 
 

House Of The Sun #311Gv

Sarasota
Ocean View
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

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

Beach View 207

Bradenton Beach
Beach Access
The Anna Maria Island Beach View 207 is a beautiful recently remodeled two bedroom, two bathroom con...

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Condo 2 / 2 / 5

Online Booking

$180 - $420
Per Night

$1260 - $2940
Per Week

 
 

The Anna Maria Island Beach Palace

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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Home 4 / 3 / 8

Online Booking

$540 - $540
Per Night

$3780 - $3780
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

 
 

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

$140 - $200
Per Night

$980 - $1400
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

 
 

Sara Sea #12, 2 Bedrooms, Wifi, Pool Access, Sleeps 4

Sarasota
Beach Access
With direct access to the #1 beach in the US, Sara Sea #12 delivers on the promise of an ideal Flori...

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Condo 2 / 2 / 6

Online Booking

$138 - $219
Per Night

$966 - $1536
Per Week

 
           
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