Siesta Key Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

Siesta Key Bay Tree #106, 2 BRs, 2 heated pools, spa, wif...

Siesta Key
Siesta Key Bay Tree #106, 2 BRs, 2 heated pools, spa, wifi, beach access Nestled on the southern ti...
Condo 2 / 2 / 6

*
Online booking available

$648 - $1480
Per Week

Apr 1 - Feb 1   20% January rentals, enter promo code 1234

Island House Beach Resort V24

Siesta Key
Island House Beach Resort, Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 2 bath villa ...
Villa 2 / 2 / 6

$160 - $246
Per Night

$1120 - $1722
Per Week

Oct 4 - Feb 1   20% off January enter promo code 1234

Island House Beach Resort 1N

Siesta Key
GULF FRONT - GROUND FLOOR UNIT!! This spectacular 2 bedrooms, 2 baths unit is 1300 sq. ft. as is loc...
Condo 2 / 2 / 4

$206 - $320
Per Night

$1442 - $2240
Per Week

Mar 29 - Feb 1   20% off January rentals - enter promo code 1234

Island House Beach Resort 17S

Siesta Key
Island House Beach Resort!! Crescent Beach, Siesta Key Florida. This beautifully maintained complex ...
Condo 2 / 2 / 4

$206 - $320
Per Night

$1442 - $2240
Per Week

Oct 12 - Feb 1   20% off January rentals – enter promo code 1234

Island House Beach Resort V17

Siesta Key
Island House Beach Resort - Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 2 bath villa...
Villa 2 / 2 / 4

$160 - $246
Per Night

$1120 - $1722
Per Week

Mar 27 - Feb 1   20% January rentals - enter promo code 1234

Island House Beach Resort 2N

Siesta Key
Crescent Beach on the Gulf of Mexico. This beautifully maintained complex is located on the widest p...
Condo 2 / 2 / 4

$206 - $320
Per Night

$1442 - $2240
Per Week

Oct 12 - Feb 1   20% January rentals, enter promo code 1234

Island House Beach Resort V37

Siesta Key
Island House Beach Resort- Siesta Key Florida, Crescent Beach - The lovely villa is located on the w...
Villa 2 / 2 / 6

$160 - $246
Per Night

$1120 - $1722
Per Week

Gulf and Bay Club 409B Beach Front

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

$590 - $1750
Per Week

Oct 5 - Feb 1   20% January rentals, enter promo code 1234

Island House Beach Resort V38

Siesta Key
Island House Beach Resort- Siesta Key Florida, Crescent Beach- This large 2 bedrooms, 2 bath villa i...
Villa 2 / 2 / 6

$160 - $246
Per Night

$1120 - $1722
Per Week

Oct 5 - Feb 1   20% January rentals, enter promo code 1234

Island House Beach Resort V6

Siesta Key
Island House Beach Resort - Siesta Key Florida, Crescent Beach - The large 2 bedrooms, 2 bath villa ...
Villa 2 / 2 / 6

$160 - $246
Per Night

$1120 - $1722
Per Week

Gulf and Bay Club 102B Beach Front, Luxury Ground Floor unit

Siesta Key
Love sunsets? How about white sand, plush beds, a choice of three pools, swans ... and a little shuf...
Condo 2 / 2 / 6

*
Online booking available

$590 - $1750
Per Week

Sep 30 - Feb 1   20% January rentals, enter promo code 1234

Island House Beach Resort V5

Siesta Key
Island House Beach Resort- Siesta Key Florida, Crescent Beach - This large villa is approx. 1000 sq....
Villa 2 / 2 / 6

$160 - $246
Per Night

$1120 - $1722
Per Week

Oct 9 - Feb 1   20% January rentals – enter promo code 1234

Island House Beach Resort V18

Siesta Key
Island House Beach Resort, Siesta Key Florida. Newly remodeled 2 bedrooms, 2 baths villa located on ...
Villa 2 / 2 / 6

$160 - $246
Per Night

$1120 - $1722
Per Week

Siesta Dunes Beach 201, 2nd Floor, Spa, Large Heated Pool...

Siesta Key
Siesta Dunes Beach 201, 2nd Floor, Spa, Large Heated Pool, Wifi Decked in pure tropical style, Sies...
Condo 2 / 2 / 6

*
Online booking available

$249 - $350
Per Night

$693 - $1995
Per Week

Apr 1 - Feb 1   20% January rentals, enter promo code 1234

Island House Beach Resort V35

Siesta Key
Island House Beach Resort - Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 2 bath unit ...
Villa 2 / 2 / 6

$160 - $246
Per Night

$1120 - $1722
Per Week

Jamaica Royale 91 Siesta Key Rental, heated pool, beach a...

Siesta Key
Jamaica Royale 91 Siesta Key Rental, heated pool, beach access,wifi How long does it take you to wa...
Condo 2 / 2 / 6

*
Online booking available

$125 - $350
Per Night

$585 - $1795
Per Week

Siesta Key Our House at the Beach 222, with Heated Pool, ...

Siesta Key
Siesta Key Our House at the Beach 222, with Heated Pool, Tennis There's plenty of room for everyone...
Condo 2 / 2 / 4

*
Online booking available

$164 - $164
Per Night

$648 - $4600
Per Week

Apr 1 - Feb 1   20% off January enter promo code 1234

Island House Beach Resort 18S

Siesta Key
Island House Beach Resort, Siesta Key Florida! This is a newly fully renovated one-bedroom, two-bath...
Condo 1 / 2 / 6

$187 - $287
Per Night

$1309 - $2009
Per Week

Gulf & Bay Club: Bayside, 2 BRs, Ground Floor, 2 pools, g...

Siesta Key
Gulf & Bay Club: Bayside, 2 BRs, Ground Floor, 2 pools, gym, tennis Just steps from the bay, our ne...
Condo 2 / 2 / 6

*
Online booking available

$125 - $350
Per Night

$650 - $1995
Per Week

Mar 29 - Feb 1   20% January rentals – enter promo code 1234

Island House Beach Resort 14N

Siesta Key
Island House Beach Resort! Crescent Beach, Siesta Key Florida. This beautifully maintained complex i...
Condo 2 / 2 / 6

$206 - $320
Per Night

$1442 - $2240
Per Week

Siesta Dunes Beach 38A, Gulf Side 2 BRs, Large Heated Poo...

Siesta Key
Siesta Dunes Beach 38A, Gulf Side 2 BRs, Large Heated Pool, Wifi Do you have children who?ll deligh...
Condo 2 / 2 / 6

*
Online booking available

$125 - $350
Per Night

$585 - $2100
Per Week

Mar 29 - Feb 1   20% January rentals - enter promo code 1234

Island House Beach Resort 4S

Siesta Key
Island House Beach Resort - Crescent Beach, Siesta Key Florida. 2nd Floor unit, 2 bedrooms, 2 baths....
Condo 2 / 2 / 6

$206 - $320
Per Night

$1442 - $2240
Per Week

Mar 27 - Feb 1   20% off January rentals - enter promo code 1234

Island House Beach Resort 11N

Siesta Key
Island House Beach Resort - Siesta Key - Crescent Beach. This beautifully maintained complex is loca...
Condo 2 / 2 / 4

$206 - $320
Per Night

$1442 - $2240
Per Week

Mar 27 - Feb 1   20% off January enter promo code 1234

Island House Beach Resor 13N

Siesta Key
Island House Beach Resort! Crescent Beach, Siesta Key Florida. This beautifully maintained complex i...
Condo 2 / 2 / 6

$206 - $320
Per Night

$1442 - $2240
Per Week

Sep 30 - Feb 1   20% January rentals - enter promo code 1234

Island House Beach Resort V11

Siesta Key
Island House Beach Resort - Siesta Key Florida - Crescent Beach - This 2 bedroom, 2 bath villa is 10...
Villa 2 / 2 / 4

$160 - $246
Per Night

$1120 - $1722
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