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

6144 Midnight Pass Rd 6N

Siesta Key
Island House Beach Resort!! Siesta Key Florida. This 2 bedrooms, 2 bath unit is 1300 sq. ft. and is ...
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

Mar 12 - Oct 1   20% Septermber rentals excluding Labor Day - enter ...

6144 Midnight Pass Rd 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 - $314
Per Night

$1442 - $2198
Per Week

Crystal Sand 406, 4th floor, Gulf View, 2 heated Pools

Siesta Key
Every sunset is a memorable experience at our condo at Crystal Sands 406 in Siesta Key. Overlooking ...
Condo 1 / 1 / 4

*
Online booking available

$518 - $1249
Per Week

Jun 15 - Oct 1   20% off September rentals excluding Labor Day - ent ...

6142 Midnight Pass Rd 12N

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

$206 - $314
Per Night

$1442 - $2198
Per Week

Siesta Key Palm and Bay Club G88 tower rental, Siesta Key...

Siesta Key
The Palm Bay Club offers all of the amenities of the finest resort hotels in a unique condo environm...
Condo 1 / 1 / 4

*
Online booking available

$125 - $400
Per Night

$695 - $1995
Per Week

Siesta Key Excelsior 107, 1st Floor, 2 heated pools, spa,...

Siesta Key
With the Bay in back and the Gulf in front, our condo at Excelsior 107 sits on a little strip of par...
Condo 2 / 2 / 6

*
Online booking available

$598 - $1499
Per Week

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

6144 Midnight Pass Rd 5N

Siesta Key
Island House Beach Resort - Crescent Beach, Siesta Key. Gulf Front Unit, 3rd Floor, Panoramic Views....
Condo 2 / 2 / 4

$206 - $314
Per Night

$1442 - $2198
Per Week

Mar 12 - Oct 1   20% off September rentals excluding Labor Day - ent ...

6146 Midnight Pass Rd 11S

Siesta Key
Island House Beach Resort - Siesta Key, Crescent Beach. This luxury apartment is located on 280 ft. ...
Condo 2 / 2 / 4

$206 - $314
Per Night

$1442 - $2198
Per Week

May 28 - 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

Jun 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

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

Mar 21 - Oct 1   20% September rentals excluding Labor Day - enter p ...

6144 Midnight Pass Rd 3N

Siesta Key
Island House Beach Resort!! Crescent Beach, Siesta Key Florida! Direct Gulf Front - Panoramic Views....
Condo 2 / 2 / 4

$206 - $314
Per Night

$1442 - $2198
Per Week

Mar 26 - Oct 1   20% September rentals excluding Labor Day - enter p ...

6148 Midnight Pass Rd 6S

Siesta Key
Island House Beach Resort - Siesta Key Florida - Southwest building, 3rd floor, One bed, 2 bath, Kin...
Condo 1 / 2 / 4

$187 - $281
Per Night

$1309 - $1967
Per Week

Mar 21 - Oct 1   20% off Septermber rentals excluding Labor Day - en ...

6146 Midnight Pass Rd 17S

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

$206 - $314
Per Night

$1442 - $2198
Per Week

Mar 23 - Oct 1   20% off September rentals excluding Labor Day - ent ...

6148 Midnight Pass Rd 2S

Siesta Key
Island House Beach Resort!!Ground Floor, Crescent Beach, Siesta Key Florida. This beautifully mainta...
Condo 2 / 2 / 6

$206 - $314
Per Night

$1442 - $2198
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

Jun 6 - Oct 1   20% off September rentals excluding Labor Day - ent ...

6146 Midnight Pass Rd 15S

Siesta Key
Island House Beach Resort! Crescent Beach, Siesta key Florida. This beautifully maintained complex i...
Condo 1 / 2 / 4

$187 - $281
Per Night

$1309 - $1967
Per Week

May 28 - Oct 1   20% Septermber rentals excluding Labor Day - enter ...

6144 Midnight Pass Rd 7N

Siesta Key
DIRECT GULF FRONT!! 2 Bedrooms, 2 bathrooms at Island House Beach Resort.4th Floor unit. The unit is...
Condo 2 / 2 / 6

$206 - $314
Per Night

$1442 - $2198
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

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

Siesta Key
Featuring new living room furniture, and tile floors - life at this condo is luxe. Sleeping 6 people...
Condo 2 / 2 / 6

*
Online booking available

$119 - $350
Per Night

$575 - $1595
Per Week

Our House at the Beach 504, 5th Floor, Gulf Views, with H...

Siesta Key
Just steps from a private walkway to the beach, our townhouse overlooking the beach Siesta Key is th...
Condo 2 / 2 / 6

*
Online booking available

$114 - $166
Per Night

$518 - $1249
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

Aloha Kai 50 Siesta Key Florida with heated pool & beach ...

Siesta Key
Aloha Kai is a 5 acre Oceanside (Gulfside) vacation retreat tucked away on the powder sand shores of...
Condo 2 / 2 / 6

*
Online booking available

$95 - $250
Per Night

$463 - $1395
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