Siesta Key Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

Gulf and Bay Club: Bayside 1303-D, 2 Bedrooms, Sleeps 6, ...

Siesta Key
When you pull up to the Gulf and Bay Club: Bayside 1303-D you will know right away that you made the...
Condo 2 / 2 / 6

*
Online booking available

$100 - $600
Per Night

$795 - $2634
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

$100 - $600
Per Night

$795 - $2634
Per Week

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

Siesta Key
Harbor Towers 324 is a cozy 1 bedroom/ 1 bath Siesta Key condo that sleeps 2-4. Guests will feel rig...
Condo 1 / 1 / 4

*
Online booking available

$93 - $298
Per Night

$650 - $1788
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

$100 - $303
Per Night

$900 - $1860
Per Week

Casa de Mariposa 5540, 3 Bedroom, Gulfview, Elevator, Hea...

Siesta Key
Casa de Mariposa is a beautifully designed 3 bedroom, 3 bathroom home with southern exposure, a heat...
Home 3 / 3 / 8

*
Online booking available

$100 - $900
Per Night

$2000 - $4200
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

$79 - $196
Per Night

$550 - $1375
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 & Bay Club ...
Condo 2 / 2 / 6

*
Online booking available

$107 - $286
Per Night

$750 - $2000
Per Week

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

Siesta Key
How long does it take you to walk 100 yards? Not very long at all. While on vacation at Crescent Bea...
Condo 2 / 2 / 6

*
Online booking available

$99 - $450
Per Night

$695 - $2394
Per Week

Siesta Dunes 8-205, 2nd Floor, Spa, Beach, Large Heated Pool

Siesta Key
Featuring beautiful wood floors, Siesta Dunes Beach 205 in Siesta Key, Florida is an ideal choice fo...
Condo 2 / 2 / 4

*
Online booking available

$100 - $600
Per Night

$850 - $2754
Per Week

Casa Siesta, ground floor, 2 bedrooms, walk to Siesta Key...

Siesta Key
Casa Siesta makes fun in the sun so easy! The 2-bedroom, ground-floor condo is just a short walk fro...
Condo 2 / 1 / 4

*
Online booking available

$71 - $330
Per Night

$495 - $1695
Per Week

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

Siesta Key
Nestled on the southern tip of Siesta Key is our ground-floor condo, Bay Tree Club 106. Located in a...
Condo 2 / 2 / 6

*
Online booking available

$93 - $298
Per Night

$650 - $1788
Per Week

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

Siesta Key
Love sunsets? How about white sand, plush beds, a choice of three pools, swans ... and a little shuf...
Condo 2 / 2 / 4

*
Online booking available

$107 - $286
Per Night

$750 - $2000
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 ...
Condo 2 / 2.5 / 6

*
Online booking available

$99 - $500
Per Night

$695 - $2394
Per Week

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

Siesta Key
Decked in pure tropical style, Siesta Dunes Beach 201 in Siesta Key, Florida is an ideal choice for ...
Condo 2 / 2 / 6

*
Online booking available

$100 - $600
Per Night

$795 - $2634
Per Week

Crescent Street 1138 B, 1 bedrooms, pool, pet friendly, w...

Siesta Key
For those who are all about “the Beach life,” Crescent Street 1113B brings an opportunity to soak in...
Condo 1 / 1 / 4

*
Online booking available

$85 - $420
Per Night

$595 - $1914
Per Week

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

$99 - $450
Per Night

$695 - $2394
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

$100 - $600
Per Night

$795 - $2634
Per Week

Gulf and Bay Club 409B, 2 Bedrooms, Beach Front, Heated P...

Siesta Key
Perfect for guests looking for a rental of one month or longer, your time spent at Siesta Key Gulf &...
Condo 2 / 2 / 4

*
Online booking available

$107 - $286
Per Night

$750 - $2000
Per Week

Sunset Royale 200, 2 Bedrooms, Gulf View, 2nd Floor, Slee...

Siesta Key
Sunset Royale 200 is literally across the street from Siesta Beach and the Gulf of Mexico. The only ...
Condo 2 / 2 / 4

*
Online booking available

$100 - $600
Per Night

$795 - $2634
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 Twi...
Condo 1 / 1 / 4

*
Online booking available

$99 - $500
Per Night

$695 - $2394
Per Week

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

Siesta Key
Looking for a home away from home as you embark upon your upcoming vacation, Polynesian Gardens Vill...
Condo 2 / 2 / 4

*
Online booking available

$100 - $480
Per Night

$750 - $2600
Per Week

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

Siesta Key
Siesta Key is one of the premier beach vacation destinations in America. When you stay at Gulf Holid...
Condo 1 / 1 / 4

*
Online booking available

$71 - $330
Per Night

$495 - $1695
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...
Condo 2 / 2 / 6

*
Online booking available

$99 - $480
Per Night

$695 - $2394
Per Week

Casa de Mariposa Mansion, 6 Bedroom, Gulf View, Heated Po...

Siesta Key
Welcome to your Island getaway at Casa de Mariposa, a beautifully designed 6 bedroom, 6 bathroom man...
Home 6 / 6 / 16

*
Online booking available

$100 - $1800
Per Night

$5000 - $9000
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 ...
Condo 2 / 2.5 / 5

*
Online booking available

$99 - $500
Per Night

$695 - $2394
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