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 #316Gf
2 bedroom Sarasota Condo Vacation Rental - Ocean Front Condo
2 BR/ 2.00 BA Sleeps 4
More Info
House Of The Sun #308Gv
2 bedroom Sarasota Condo Vacation Rental - Ocean View Condo
2 BR/ 2.00 BA Sleeps 4
More Info
Bay View Inn 201-308 2nd St
1 bedroom Bradenton Beach Condo Vacation Rental Condo
1 BR/ 1.00 BA Sleeps 4
More Info
 
 
 
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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 #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

 
 

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 #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 #308Gv

Sarasota
Ocean View
Virtual Tour You'll know you're on vacation but with all of the comforts of home! Enjoy this beauti...

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Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
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

 
 

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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Waterlefe 01

Bradenton
This stunning 3 bedroom, 2 bathroom townhome will make you feel right at home, and offers everything...

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Home 3 / 2 / 6

Online Booking

$125 - $180
Per Night

$875 - $1260
Per Week

 
 

SunsetTerrace 206-2312 Gulf Dr

Bradenton Beach
Located in beautiful Bradenton Beach, “Sunset Terrace” is the perfect Anna Maria Island vacation ren...

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Condo 2 / 2 / 4

Online Booking

$220 - $370
Per Night

$1540 - $2590
Per Week

 
 

Sunset Terrace 205

Bradenton Beach
Enjoy the gulf coast waters and sandy beaches from this Bradenton Beach vacation condo. What a wond...

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Condo 2 / 2 / 6

Online Booking

$210 - $330
Per Night

$1470 - $2310
Per Week

 
 

House Of The Sun #210Gv

Sarasota
Ocean View
Contemporary and stylish Unit 210 provides the utmost in an island retreat. Relax and enjoy fabulous...

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Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

River Strand 25

Bradenton
Enjoy the nearby Sarasota cultural venues, shopping and world-class beaches. Checkout the Boardwak a...

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Home 3 / 2 / 6

Online Booking

$170 - $235
Per Night

$1190 - $1645
Per Week

 
 

House Of The Sun #202Gs

Sarasota
This Gulf Side unit is bright and airy accented with blues and browns with tile throughout. There ar...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

House Of The Sun #411Gv

Sarasota
Ocean View
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

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

Anna Maria Island Club Unit 18

Bradenton Beach
2 Bedroom, 2 Bath (sleeps 4) - "Anna Maria Island Club" - 2600 Gulf Drive N. Unit #18, Bradenton Bea...

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Condo 2 / 2 / 4

Online Booking

$250 - $440
Per Night

$1750 - $3080
Per Week

 
 

River Pointe 01

Bradenton
Lake View
River Pointe is a boating community along the Manatee River with nearby River Isles Golf Course.Grea...

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Home 4 / 2 / 8

Online Booking

$170 - $245
Per Night

$1190 - $1715
Per Week

 
 

House Of The Sun #408Gv

Sarasota
Ocean View
This newly renovated Floridian condo boasts a Key West theme throughout. The kitchen, living room an...

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Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

Siesta Shores 13, 3 Bedrooms, Pet Friendly, Sleeps 8

Sarasota
Beach Access
Situated just steps away from the "world's finest, whitest sand" and all of the enjoyment that Siest...

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Condo 3 / 2 / 8

Online Booking

$128 - $385
Per Night

$895 - $2695
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

 
 

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

Siesta Key
Beach Access
The accolades keep pouring in. Guests and media alike rate the Palm Bay Club as a perfect destinatio...

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Condo 1 / 1 / 4

Online Booking

$107 - $366
Per Night

$750 - $2561
Per Week

 
 

Tara 05

Bradenton
Located in Tara this vacation rental will be sure to meet your every need! Want to enjoy the sun by ...

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Home 3 / 2 / 6

Online Booking

$170 - $245
Per Night

$1190 - $1715
Per Week

 
 

The Anna Maria Island Beach Palms 7A

Bradenton Beach
The Anna Maria Island Beach Palms 7A is located with-in walking distance of Anna Maria Island's best...

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Condo 2 / 2 / 6

Online Booking

$220 - $420
Per Night

$1540 - $2940
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

 
 

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 #410Gv

Sarasota
Ocean View
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

$289 - $289
Per Night

$1380 - $2021
Per Week

 
           
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