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 #311Gv
2 bedroom Sarasota Condo Vacation Rental - Ocean View Condo
2 BR/ 2.00 BA Sleeps 6
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House Of The Sun #508Gv
2 bedroom Sarasota Condo Vacation Rental - Ocean View Condo
2 BR/ 2.00 BA Sleeps 6
More Info
Anna Maria Island Club Unit 40
2 bedroom Bradenton Beach Condo Vacation Rental Condo
2 BR/ 2.00 BA Sleeps 4
More Info
 
 
 
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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 #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 #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

 
 

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 #508Gv

Sarasota
Ocean View
Come stay in this beautiful, remodeled and redecorated ocean view apartment. It truly has that light...

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Condo 2 / 2 / 6

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
May 1 - May 26   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 #505Gs

Sarasota
This Gulf Side unit has new tile throughout the common areas and blue carpet in the bedrooms. This ...

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Condo 2 / 2 / 6

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

Gulf and Bay Club 102B, Beach Front, 2 Bedrooms, Ground F...

Siesta Key
Beach Access, Beach Front, Ocean View
Love sunsets? How about white sand, plush beds, a choice of three pools, swans ... and a little shuf...

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Condo 2 / 2 / 6

Online Booking

$125 - $304
Per Night

$875 - $2125
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 #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

 
 

House Of The Sun #510Gv

Sarasota
Ocean View
Virtual Tour This newly renovated Gulf View unit has tile throughout the common areas and carpet in...

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Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
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 - $304
Per Night

$875 - $2125
Per Week

 
 

Hibiscus

Bradenton Beach
Stunning views on Anna Maria. Less than a block to the Gulf of Mexico beaches. Welcome to paradise ...

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Home 2 / 2 / 6

Online Booking

$215 - $380
Per Night

$1505 - $2660
Per Week

 
 

Beach Palms 2A

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

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Condo 2 / 2 / 6

Online Booking

$220 - $420
Per Night

$1540 - $2940
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...

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Condo 2 / 2 / 4

Online Booking

$139 - $393
Per Night

$973 - $2754
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

 
 

Palm Bay Club Bayside 328, 2 Bedrooms, Heated Pool, Tenni...

Sarasota
Beach Access
Are you ready for a great escape? If so, Palm Bay Club’s Bayside 328 is the perfect spot for you. Wi...

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Condo 2 / 2 / 4

Online Booking

$136 - $428
Per Night

$950 - $2994
Per Week

 
 

Siesta Dunes Beach 38A, 2 Bedrooms, Ground Floor, Heated ...

Siesta Key
Do you have children who’ll delight in the geckos and insects they can discover in the garden? Or do...

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Condo 2 / 2 / 6

Online Booking

$99 - $479
Per Night

$695 - $2394
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

 
 

Bay View Inn 201-308 2nd St

Bradenton Beach
Recently updated, Bay View Inn 201 is a charming and stylish Bradenton Beach vacation rental condo a...

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Condo 1 / 1 / 4

Online Booking

$115 - $180
Per Night

$805 - $1260
Per Week

 
 

The Anna Maria Island Beach Sands 101

Bradenton Beach
Beach Access
The Anna Maria Island Beach Sands #101 overlooks the Gulf of Mexico is located with-in walking dista...

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Condo 2 / 2 / 6

Online Booking

$205 - $440
Per Night

$1435 - $3080
Per Week

 
 

House Of The Sun #506Gs

Sarasota
Virtual Tour A 2 bedroom 2 bath accommodation on the 5th floor, (accessible via two outside elevato...

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Condo 2 / 2 / 4

Online Booking

$247 - $247
Per Night

$1196 - $1732
Per Week

 
 

River Strand 49

Bradenton
Located inside the River Strand community, this Bradenton vacation townhome is only 20 minutes from ...

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Condo 2 / 2 / 4

Online Booking

$135 - $205
Per Night

$945 - $1435
Per Week

 
 

PBC 1279 Edgewater Circle

Bradenton
Stylishly decorated and spaciously accommodating, you’ll fall in love with Florida living when you s...

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Condo 2 / 2 / 6

Online Booking

$135 - $175
Per Night

$945 - $1225
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

$185 - $325
Per Night

$1295 - $2275
Per Week

 
           
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