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 #510Gv
2 bedroom Sarasota Condo Vacation Rental - Ocean View Condo
2 BR/ 2.00 BA Sleeps 4
More Info
House Of The Sun #314Gv
2 bedroom Sarasota Condo Vacation Rental - Ocean View Condo
2 BR/ 2.00 BA Sleeps 4
More Info
Bollinger Duplex, B
1 bedroom Holmes Beach Home Vacation Rental Home
1 BR/ 1.00 BA Sleeps 6
More Info
 
 
 
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House Of The Sun #309Gv

Sarasota
Ocean View
You will feel right at home in this cozy Gulf View unit. It has new leather furniture and a 42” LCD...

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Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

House Of The Sun #315Gf

Sarasota
Ocean Front
This newly rennovated Gulf Front unit will make you feel right at home with it's warm and cozy decor...

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Condo 2 / 2 / 6

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

 
 

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

 
 

House Of The Sun #314Gv

Sarasota
Ocean View
This Gulf View unit has tile throughout common areas, 2 full size sofas and a leather recliner. The ...

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Condo 2 / 2 / 4

Online Booking

$289 - $289
Per Night

$1380 - $2021
Per Week

 
 

Luxury Perico Island Beach House -close to Anna Maria Island

Bradenton
Beach Access, Golf nearby, Lake View, Ocean nearby
Watch the birds from your waterfront beach house, swim in the luxurious pool or ride your bike to Ma...

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Home 3 / 2.5 / 6

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Owner
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For Rates

 
 

Gulf Holidays 15, 1 Bedroom, 2nd Floor, Heated Pool, Slee...

Siesta Key
Beach Access
Budget-friendly and just a block from a beach rated #1 in the country, it’s easy to see why Gulf Hol...

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Condo 1 / 1 / 4

Online Booking

$107 - $246
Per Night

$750 - $1725
Per Week

 
 

The Anna Maria Island Beach Sands 203

Bradenton Beach
Beach Access
FAMILY/CHILD FRIEDLY CONDOMINIUM. Surrounded by water with the Gulf of Mexico to the west, the Intr...

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Condo 2 / 2 / 4

Online Booking

$175 - $400
Per Night

$1225 - $2800
Per Week

 
 

River Strand 20

Bradenton
Enjoy the warm and sunny beaches of the Florida Guld Coast, and Sarasota too! Located in the presti...

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Home 4 / 3 / 10

Online Booking

$240 - $290
Per Night

$1680 - $2030
Per Week

 
 

The Anna Maria Island Beach Castle

Bradenton Beach
FAMILY/CHILD FRIEDLY CONDOMINIUM. The Beach Castle is located with-in walking distance of Anna Mari...

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Condo 2 / 2 / 6

Online Booking

$175 - $400
Per Night

$1225 - $2800
Per Week

 
 

Cove At Sandy Pointe 205a

Holmes Beach
Unit 205A, Cove at Sandy Pointe, at 3601 East Bay Drive is a bright and airy 2 bedroom, 2 bath condo...

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Condo 2 / 2 / 6

Online Booking

$105 - $215
Per Night

$735 - $1505
Per Week

 
 

Sunset Terrace 108

Bradenton Beach
Sunset Terrace Condo #108 is a newly renovated Gulf front condo with a heated pool, located at 2312 ...

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Condo 2 / 2 / 6

Online Booking

$220 - $380
Per Night

$1540 - $2660
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

$170 - $250
Per Night

$1190 - $1750
Per Week

 
 

Lagoon Views & Sandy Toes! Make Yourself At Home on Ami! ...

Bradenton Beach
Lagoon Views & Sandy Toes! Make Yourself At Home on Ami! Lowest Rates! Settle into your own corner ...

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Condo 2 / 2 / 6

Online Booking

$539 - $1500
Per Week

 
 

Bay Oaks D-22, 2 Bedrooms, Heated Pool Access, Wifi, Sies...

Sarasota
Beach Access
Experience Siesta Key from Bay Oaks D-22 and enjoy the beautiful pool view! This beautifully updated...

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Condo 2 / 2.5 / 6

Online Booking

$136 - $384
Per Night

$950 - $2688
Per Week

 
 

Garden Home

Holmes Beach
The Garden Home, located at 419 Clark Drive in Holmes Beach is a spectacular, three bedrooms, and tw...

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Home 3 / 2 / 8

Online Booking

$315 - $605
Per Night

$2205 - $4235
Per Week

 
 

Bright & Beachy 1 BR/1 BA Located Steps to the Sand!

Bradenton Beach
Settle into your own corner of island life at this comfortable, 1 bedroom/1 bathroom super cute cond...

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Condo 1 / 1 / 4

Online Booking

$539 - $1300
Per Week

 
 

Alamanda Villas 5

Holmes Beach
Alamanda Villas, located at 102 39th Street in Holmes Beach is a charming beachside complex featurin...

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Condo 1 / 1 / 4

Online Booking

$170 - $315
Per Night

$1190 - $2205
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 - $246
Per Night

$750 - $1725
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 - $274
Per Night

$795 - $1917
Per Week

 
 

Castnetter Beach Resort 10

Holmes Beach
Castnetter Beach Resort 10 is a delightful island locale located directly across the street from the...

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Home 1 / 1 / 4

Online Booking

$125 - $210
Per Night

$875 - $1470
Per Week

 
 

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

 
 

Casa Playa Combo

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

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Home 8 / 8 / 20

Online Booking

$665 - $1155
Per Night

$4655 - $8085
Per Week

 
 

Siesta Shores B13, 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

$171 - $549
Per Night

$1195 - $3844
Per Week

 
 

White Sands Village 205, 2 Bedrooms, Heated Pool, Wifi, S...

Siesta Key
Beat a path to the beach every day from your own breezy lanai when you stay at this ground-floor con...

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Condo 2 / 2 / 6

Online Booking

$107 - $219
Per Night

$750 - $1532
Per Week

 
           
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