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.

Refine Your Search:
Destination
Check-In Check-Out
Amenities
Enter Keywords:
 
 
 
 
Featured Listings
 
House Of The Sun #210Gv
2 bedroom Sarasota Condo Vacation Rental - Ocean View Condo
2 BR/ 2.00 BA Sleeps 4
More Info
House Of The Sun #305Gs
2 bedroom Sarasota Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 6
More Info
Siesta Key Excelsior 306, ...
3 bedroom Siesta Key Condo Vacation Rental Condo
3 BR/ 2.00 BA Sleeps 6
More Info
 
 
 
  Sort by:  Type BR/BA/Sleeps Price  
 

House Of The Sun #210Gv

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

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

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

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...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
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...

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

Online Booking

$289 - $289
Per Night

$1380 - $2021
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...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 6

Online Booking

$289 - $289
Per Night

$1380 - $2021
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...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

Anna Maria Island Club Unit 27

Bradenton Beach
2 Bedroom, 2 Bathroom (Sleeps 4) – “Anna Maria Island Club 27” – 2600 Gulf Drive in Bradenton Beach....

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

Online Booking

$270 - $460
Per Night

$1890 - $3220
Per Week

 
 

Casa Playa Combo

Bradenton Beach
This rental home on Anna Maria Island sleeps up to 20 and comes fully equipped. This Bradenton Beac...

View Details and Book Online    Send Inquiry
Home 8 / 8 / 20

Online Booking

$685 - $1195
Per Night

$4795 - $8365
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...

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

Online Booking

$289 - $289
Per Night

$1380 - $2021
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 ...

View Details and Book Online    Send Inquiry
Condo 2 / 2.5 / 5

Online Booking

$99 - $500
Per Night

$695 - $2394
Per Week

 
 

Hawk's Nest Runaway Bay Unit 272

Bradenton Beach
2 Bedroom, 2 Bath (sleeps 6) - Runaway Bay Condominium: "Hawk's Nest" - 1801 Gulf Drive North Unit #...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 6

Online Booking

$240 - $345
Per Night

$1680 - $2415
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...

View Details and Book Online    Send Inquiry
Condo 1 / 1 / 4

Online Booking

$99 - $450
Per Night

$695 - $2394
Per Week

 
 

House Of The Sun #208Gs

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

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

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

Anna Maria Ahhh

Bradenton Beach
To really get away from it all, one needs their clear head. Send all your cares drifting by enjoying...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 6

Online Booking

$275 - $470
Per Night

$1925 - $3290
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 ...

View Details and Book Online    Send Inquiry
Home 3 / 3 / 8

Online Booking

$100 - $900
Per Night

$2225 - $4550
Per Week

 
 

House Of The Sun #402Gs

Sarasota
Virtual Tour This Gulf Side unit has new installed tile inthe common areas, with carpet in both bed...

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

Online Booking

$247 - $247
Per Night

$1196 - $1732
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...

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

Online Booking

$100 - $550
Per Night

$850 - $2594
Per Week

 
 

The Anna Maria Island Beach Palms 2B

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

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 6

Online Booking

$220 - $420
Per Night

$1540 - $2940
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 ...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 6

Online Booking

$107 - $286
Per Night

$750 - $2000
Per Week

 
 

Vista Hermosa, 2 Bedrooms, Pool, Wireless Internet, Sleeps 5

Sarasota
Beach Access
Beautiful, updated villa in desirable Vista Hermosa – condo on Siesta Key in Sarasota. One of the fi...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 5

Online Booking

$93 - $298
Per Night

$650 - $1788
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 &...

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

Online Booking

$107 - $286
Per Night

$750 - $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...

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

Online Booking

$100 - $600
Per Night

$795 - $2634
Per Week

 
 

River Strand 53

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

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

Online Booking

$135 - $205
Per Night

$945 - $1435
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...

View Details and Book Online    Send Inquiry
Condo 3 / 2 / 6

Online Booking

$100 - $303
Per Night

$900 - $1860
Per Week

 
 

Bradenton Beach Club Unit 224

Bradenton Beach
Enjoy a week in tropical island luxury when you visit the beautiful “Bradenton Beach Club” unit 224!...

View Details and Book Online    Send Inquiry
Condo 2 / 2 / 6

Online Booking

$235 - $355
Per Night

$1645 - $2520
Per Week

 
 

Club Bamboo South 223

Bradenton Beach
Beach Access, Beach Front
Located on Bradenton Beach, Club Bamboo South offers guests a private beach and outdoor pool. This ...

View Details and Book Online    Send Inquiry
Condo 0 / 1 / 4

Online Booking

$100 - $265
Per Night

$700 - $1855
Per Week

 
           
More Beach and Coastal Locations and Properties