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 #302Gs
2 bedroom Sarasota Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 6
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House Of The Sun #208Gs
2 bedroom Sarasota Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 4
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House Of The Sun #213Gv
2 bedroom Sarasota Condo Vacation Rental - Ocean View Condo
2 BR/ 2.00 BA Sleeps 6
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House Of The Sun #503Gs

Sarasota
Virtual Tour This Gulf side unit has beautiful tile throughout the common area and bathrooms. Off w...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

House Of The Sun #414Gf

Sarasota
Ocean Front
This Gulf Front condo recently underwent a renovation that boasts new granite counter-tops and cabin...

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Condo 2 / 2 / 6

Online Booking

$343 - $343
Per Night

$1693 - $2400
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

 
 

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 #302Gs

Sarasota
Virtual Tour The gulf side unit has recently been updated with new kitchen appliances, soft close c...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
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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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

 
 

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

 
 

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

 
 

Safari Suite

Bradenton Beach
  The Safari Suite is located at 1105 Gulf Drive South in Bradenton Beach on Anna Maria Island, FL....

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Home 1 / 1 / 4

Online Booking

$140 - $250
Per Night

$1015 - $1750
Per Week

 
 

Jamaica Royale 101, 2 Bedrooms, 3 Heated Pools, Wifi, Sle...

Siesta Key
A beach holiday doesn’t get any better when you combine good food and a great place to stay in the m...

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Condo 2 / 2 / 6

Online Booking

$99 - $314
Per Night

$556 - $2195
Per Week

 
 

House Of The Sun #216Gf

Sarasota
Ocean Front
This newly renovated Gulf Front unit offers pristine views of the beautiful turquoise waters and whi...

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Condo 2 / 2 / 6

Online Booking

$343 - $343
Per Night

$1693 - $2400
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

 
 

Jamaica Royale Tower 24, 2 Bedrooms, 3 Heated Pools, Slee...

Siesta Key
Beach Access, Ocean View
Enjoy sunset views and warm Gulf breezes from the balcony of this 2 bedroom 2 bath Tower unit 24. I...

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Condo 2 / 2 / 6

Online Booking

$171 - $459
Per Night

$1195 - $2777
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

 
 

Anna Maria Ahhh

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

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Condo 2 / 2 / 4

Online Booking

$250 - $440
Per Night

$1750 - $3080
Per Week

 
 

River Strand 46

Bradenton
Nearby about 20 minutes you`ll find the white sandy beaches of the Florida Gulf Coast.A beautiful 3 ...

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Home 3 / 2 / 6

Online Booking

$185 - $255
Per Night

$1295 - $1785
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

 
 

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

 
 

Sunset Villa 3

Bradenton Beach
Sunset Villa awaits the vacationer in you. Located in this well-kept condo complex directly across f...

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Condo 2 / 1.5 / 4

Online Booking

$170 - $290
Per Night

$1190 - $2030
Per Week

 
 

Casa Playa East

Bradenton Beach
Beach Access
This rental home on Anna Maria Island sleeps up to 10 and comes fully equipped. This Bradenton Beac...

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Home 4 / 3.5 / 11

Online Booking

$275 - $670
Per Night

$1925 - $4690
Per Week

 
 

Creek Wood 02

Bradenton
You won't be disappointed with this 3/2 vacation rental. Located off state road 70 in the CreekWood ...

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Home 3 / 2 / 6

Online Booking

$170 - $245
Per Night

$1190 - $1715
Per Week

 
 

Siesta Dunes Beach 201, 2 Bedrooms, Large Heated Pool, Sp...

Siesta Key
Beach Access
Decked in pure tropical style, Siesta Dunes Beach 201 in Siesta Key, Florida is an ideal choice for ...

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Condo 2 / 2 / 6

Online Booking

$114 - $371
Per Night

$636 - $2594
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 #509Gv

Sarasota
Ocean View
Virtual Tour This newly renovated Gulf View unit has new stainless steel appliances in the kitchen ...

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Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
           
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