Siesta Key Vacation Rental Getaways


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  • Pool Access
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  • Beach Front
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Sort by: Type BR/BA/Sleeps Price

Crescent Street 1138 A, 2 bedrooms, pool, walk to the beach

Siesta Key
When you stay at Crescent Street 1138A, you can walk to the east side of Siesta Key in just minutes ...
Condo 2 / 1 / 6

*
Online booking available

$114 - $274
Per Night

$795 - $1917
Per Week

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

Siesta Key
Ready to spend 28 days or more in paradise? If so, Gulf & Bay Club 102B is waiting for you. This gro...
Condo 2 / 2 / 6

*
Online booking available

$125 - $304
Per Night

$875 - $2126
Per Week

Gulf and Bay Club 305C, 2 Bedrooms, 3 pools, Gym, Spa, Wi...

Siesta Key
Roll into the lap of luxury and enjoy a unit that’s still sparkling new. Siesta Key Gulf and Bay Clu...
Condo 2 / 2 / 6

*
Online booking available

$161 - $402
Per Night

$1125 - $2815
Per Week

Siesta Key Excelsior 306, 3 Bedrooms, Pools, Tennis, Slee...

Siesta Key
With spectacular views of the beautiful trees, pond, pool and peek a boo view of the Intracoastal, y...
Condo 3 / 2 / 6

*
Online booking available

$129 - $330
Per Night

$900 - $2312
Per Week

Palm Bay Club G34, 1 Bedroom, Heated Pool, Wifi, Hot Tub,...

Siesta Key
Both TripAdvisor and Dr. Beach named Siesta Beach the country’s best beach. When you stay at Palm Ba...
Condo 1 / 1 / 4

*
Online booking available

$142 - $412
Per Night

$995 - $2881
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...
Condo 2 / 2 / 6

*
Online booking available

$114 - $274
Per Night

$795 - $1917
Per Week

Jamaica Royale 91, 2 Bedrooms, 3 Heated Pools, Wifi, Slee...

Siesta Key
In this handy ground-floor condo, you're just a short walk away from gorgeous Crescent Beach, the je...
Condo 2 / 2 / 6

*
Online booking available

$114 - $274
Per Night

$795 - $1917
Per Week

Harbor Towers Yacht & Racquet 324, 1 Bedroom, Heated Pool...

Siesta Key
Discover the power that a change of scenery can have: steal away to this charming pied-a-terre just ...
Condo 1 / 1 / 4

*
Online booking available

$107 - $219
Per Night

$750 - $1532
Per Week

Bay Oaks B-52, 2 Bedrooms, Updated Condo, Sleeps 6

Siesta Key
Featured on HGTV's Beachfront Bargain Hunt TV show! With views over a sunny, peek a boo view of the ...
Condo 2 / 2.5 / 6

*
Online booking available

$180 - $384
Per Night

$753 - $896
Per Week

Crescent Street Manor, 3 Bedrooms, Walk to Beach, Private...

Siesta Key
When you stay at Crescent Street Manor, you can walk to the east side of Siesta Key in just minutes ...
Condo 3 / 2 / 10

*
Online booking available

$199 - $659
Per Night

$1395 - $4615
Per Week

Gulf and Bay Club: Bayside 1226, 2 Bedrooms, Sleeps 6, 2 ...

Siesta Key
Just steps from the bay, our newly remodeled condo in a gated Key West-style community is the perfec...
Condo 2 / 2 / 6

*
Online booking available

$107 - $246
Per Night

$750 - $1725
Per Week

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

Siesta Key
With the top-rated beach in the country in your backyard, Palm Bay Club G46 delivers the perfect Gul...
Condo 1 / 1 / 4

*
Online booking available

$107 - $246
Per Night

$750 - $1725
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...
Condo 2 / 2 / 4

*
Online booking available

$128 - $330
Per Night

$895 - $2312
Per Week

Gulf and Bay Club 108D, 2 Bedroom, Beach Front, Ground Fl...

Siesta Key
Want to get away from everyday life and enjoy a month alongside the #1 beach in the USA? Gulf and Ba...
Condo 2 / 2 / 4

*
Online booking available

$125 - $304
Per Night

$875 - $2126
Per Week

Bay Oaks D-42, 2 Bedrooms, Siesta Key Florida, Updated Condo

Siesta Key
With 2 bedrooms and 2.5 bathrooms, Bay Oaks D-42 can accommodate a family of 5 or 2 couples with equ...
Condo 2 / 2.5 / 5

*
Online booking available

$99 - $219
Per Night

$695 - $1532
Per Week

Gulf and Bay Club 204C, 2 Bedroom, Beach Front, 3 Pools, ...

Siesta Key
Come vacation on the white sands of Siesta Beach! When you stay at our condo at Gulf and Bay Club 20...
Condo 2 / 2 / 6

*
Online booking available

$125 - $304
Per Night

$875 - $2126
Per Week

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

Siesta Key
Live the tropical life in this incredible modern condo! From the large wooden deck to the heated poo...
Condo 2 / 2 / 6

*
Online booking available

$124 - $330
Per Night

$868 - $2312
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...
Condo 2 / 2 / 6

*
Online booking available

$107 - $219
Per Night

$750 - $1532
Per Week

Twin Palms 5, 1 Bedroom, Ground Floor, Heated Pool, Wifi,...

Siesta Key
You’ll be just a one-block walk from Siesta Key, the #1 rated beach in the USA when you stay at Twin...
Condo 1 / 1 / 4

*
Online booking available

$107 - $246
Per Night

$750 - $1725
Per Week

Midnight Cove II 432, 2 Bedrooms, Large Heated Pool, Spa,...

Siesta Key
From the spacious balcony of this 3rd-floor condo, you can enjoy sun or shade, watch exotic birds vi...
Condo 2 / 1.5 / 4

*
Online booking available

$114 - $274
Per Night

$795 - $1917
Per Week

Beachaven 52, 1 bedroom, Ground Floor, Pool, Sleeps 4

Siesta Key
Imagine this: You step out your front door, and there, at the end of a walkway flanked by shrubbery ...
Condo 1 / 2 / 4

*
Online booking available

$113 - $203
Per Night

$793 - $1418
Per Week

Bay Tree Club 106, 2 Bedrooms, 2 Heated Pools, Spa, Wifi,...

Siesta Key
With the Gulf of Mexico just steps from your back door and beautiful Sarasota Bay a couple minutes’ ...
Condo 2 / 2 / 6

*
Online booking available

$107 - $219
Per Night

$750 - $1532
Per Week

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

Siesta Key
This unit has been newly renovated in the fall of 2017. Stunning seaside decor, new kitchen, baths, ...
Condo 2 / 2 / 6

*
Online booking available

$136 - $384
Per Night

$950 - $2688
Per Week

Polynesian Gardens Villa P6, 2 Bedrooms, Heated Pool, Car...

Siesta Key
Welcome to your home in paradise! This standalone 2-bedroom villa offers privacy and relaxation for ...
Condo 2 / 2 / 4

*
Online booking available

$100 - $191
Per Night

$700 - $1339
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...
Condo 1 / 1 / 4

*
Online booking available

$107 - $246
Per Night

$750 - $1725
Per Week

Siesta Key Getaway Information

Travelers looking for a Siesta Key vacation home rental will be delighted with the wonderful year-round weather and breathtaking landscapes. The average summer highs reach the low 90s and the winter highs tend to be in the low 70s. So no matter what time of year it is, you'll be able to stroll around Siesta Key in your warm weather clothes, taking in the amazing scenery and native wildlife such as tropical birds and dolphins.

A Siesta Key vacation home 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'll 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'll 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 rental.

More Getaway Locations and Properties