Siesta key Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price
May 21 - Oct 1   20% September rentals excluding Labor Day - enter p ...

6144 Midnight Pass Rd 8N

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

$206 - $314
Per Night

$1442 - $2198
Per Week

Mar 28 - Oct 1   20% off Septermber rentals excluding Labor Day - en ...

6146 Midnight Pass Rd 14S

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

$206 - $314
Per Night

$1442 - $2198
Per Week

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

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

$518 - $1249
Per Week

Mar 12 - Oct 1   20% off September rentals exluding Labor Day- enter ...

6148 Midnight Pass Rd 1S

Siesta key
DIRECT GULF FRONT, GROUND FLOOR! Siesta Key, Crescent Beach This unit is located in our southwest bu...
Condo 2 / 2 / 4

$206 - $314
Per Night

$1442 - $2198
Per Week

May 23 - Oct 1   20% September rentals excluding Labor Day, enter pr ...

6150 Midnight Pass Rd V26

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

$160 - $241
Per Night

$1120 - $1687
Per Week

May 23 - Oct 1   20% September rentals excluding Labor Day - enter p ...

6150 Midnight Pass Rd V2

Siesta Key
Island House Beach Resort - Siesta Key Florida, Crescent Beach - This NEWLY REMODELED, 2 bedrooms, 2...
Villa 2 / 2 / 6

$160 - $241
Per Night

$1120 - $1687
Per Week

Mar 16 - Oct 1   20% off September rentals excluding Labor Day - ent ...

6146 Midnight Pass Rd 10S

Siesta Key
Island House Beach Resort! Siesta Key Florida, Crescent Beach. Ground floor unit. This 2 bedroom, 2 ...
Condo 2 / 2 / 4

$206 - $314
Per Night

$1442 - $2198
Per Week

May 11 - Oct 1   20% off September rentals excluding Labor Day - ent ...

6146 Midnight Pass Rd 12S

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

$206 - $314
Per Night

$1442 - $2198
Per Week

May 23 - Oct 1   20% September rentals excluding Labor Day, enter pr ...

6150 Midnight Pass Rd V9

Siesta Key
Island House Beach Resort - Siesta Key Florida, Crescent Beach - This large villa is approx. 1000 sq...
Villa 2 / 2 / 4

$160 - $241
Per Night

$1120 - $1687
Per Week

Mar 9 - Oct 1   20% September rentals excluding Labor Day, enter pr ...

6150 Midnight Pass Rd V15

Siesta Key
Island House Beach Resort! Crescent Beach, Siesta Key Florida. This attractive 2 bedroom, 2 bath vil...
Villa 2 / 2 / 6

$160 - $241
Per Night

$1120 - $1687
Per Week

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

Siesta Key
The moment you arrive at Gulf & Bay Bayside, you?ll appreciate the beauty, serenity, and charm of th...
Condo 2 / 2 / 6

*
Online booking available

$119 - $350
Per Night

$575 - $1595
Per Week

Mar 30 - Oct 1   20% Septermber rentals excluding Labor Day - enter ...

6150 Midnight Pass Rd V19

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

$160 - $241
Per Night

$1120 - $1687
Per Week

May 25 - Oct 1   20% September rentals excluding Labor Day, enter pr ...

6150 Midnight Pass Rd V32

Siesta Key
Island House Beach Resort, Siesta Key Florida, Crescent Beach - This lovely unit is approx. 1000 sq....
Villa 2 / 2 / 4

$160 - $241
Per Night

$1120 - $1687
Per Week

Castaway Cove 3B, on lagoon near beach, pet friendly, Sie...

Siesta Key
Overlooking Blind Pass Lagoon just a few blocks to Turtle Beach is our Siesta Key condo, Castaway Co...
Condo 2 / 2 / 5

*
Online booking available

$95 - $250
Per Night

$454 - $1395
Per Week

Feb 2 - Oct 1   20% Septermber rentals excluding Labor Day - enter ...

6148 Midnight Pass Rd 8S

Siesta Key
Island House Beach Resort! Siesta Key Florida - Crescent Beach. This luxury apartment is part of Isl...
Condo 2 / 2 / 4

$206 - $314
Per Night

$1442 - $2198
Per Week

Apr 17 - Oct 1   20% September rentals excluding Labor Day - enter p ...

6150 Midnight Pass Rd V16

Siesta Key
Island House Beach Resort! Siesta Key, Florida, Crescent Beach. This large 2 bedrooms, 2 bath unit i...
Villa 2 / 2 / 5

$160 - $241
Per Night

$1120 - $1687
Per Week

6142 Midnight Pass Rd

Siesta Key
Island House Beach Resort! Newly remodeled gulf view apartment. Brand new kitchen, bathrooms, wood a...
Condo 2 / 2 / 6

$206 - $314
Per Night

$1442 - $2198
Per Week

May 16 - Oct 1   20% September rentals excluding Labor Day, enter pr ...

6150 Midnight Pass Rd V6

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

$160 - $241
Per Night

$1120 - $1687
Per Week

Feb 7 - Oct 1   20% September rentals excluding Labor Day, enter pr ...

6150 Midnight Pass Rd V23

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

$160 - $241
Per Night

$1120 - $1687
Per Week

Mar 19 - Oct 1   20% off September rentals excluding Labor Day - ent ...

6142 Midnight Pass Rd 11N

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

$206 - $314
Per Night

$1442 - $2198
Per Week

Apr 27 - Oct 1   20% off September rentals excluding Labor Day - ent ...

6142 Midnight Pass Rd 16N

Siesta Key
Island House Beach Resort! Newly remodeled!! Crescent Beach, Siesta Key Florida! This attractive com...
Condo 2 / 2 / 6

$206 - $314
Per Night

$1442 - $2198
Per Week

Feb 2 - Oct 1   20% September rentals excluding Labor Day, enter pr ...

6150 Midnight Pass Rd V27

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

$160 - $241
Per Night

$1120 - $1687
Per Week

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

Siesta Key
An idyllic ocean side condo perfect for energetic kids or families seeking added privacy, Siesta Dun...
Condo 2 / 2 / 6

*
Online booking available

$119 - $350
Per Night

$575 - $1595
Per Week

Feb 2 - Oct 1   20% Septermber rentals excluding Labor Day - enter ...

6142 Midnight Pass Rd 9N

Siesta Key
Island House Beach Resort! Siesta Key Florida, Crescent Beach. Ground floor unit. This 2 bedroom, 2 ...
Condo 2 / 2 / 6

$206 - $314
Per Night

$1442 - $2198
Per Week

May 18 - Oct 1   20% September rentals excluding Labor Day, enter pr ...

6150 Midnight Pass Rd V3

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

$160 - $241
Per Night

$1120 - $1687
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.

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