Siesta Key Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price
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

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

6148 Midnight Pass Rd 4S

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

$206 - $314
Per Night

$1442 - $2198
Per Week

Mar 12 - 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

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

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

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

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

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

Siesta Key
Just steps from a private walkway to the beach, our townhouse overlooking the lake at Siesta Key is ...
Condo 2 / 2 / 4

*
Online booking available

$114 - $166
Per Night

$529 - $1249
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

Siesta Dunes Beach 104, Siesta Key Gulf, Spa, Large Heate...

Siesta Key
Decked in tropical style, Siesta Dunes 104 is an ideal choice for families to spend their daytime ho...
Condo 2 / 2 / 6

*
Online booking available

$119 - $350
Per Night

$575 - $1595
Per Week

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

6146 Midnight Pass Rd 13S

Siesta Key
Enjoy the view of the white sand of Crescent Beach and the azure waters of the Gulf of Mexico from t...
Condo 2 / 2 / 4

$206 - $314
Per Night

$1442 - $2198
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 / 6

*
Online booking available

$451 - $1750
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

Apr 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

Siesta Key Gulf and Bay Club 305 C Building, 3 pools, fit...

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

$564 - $1750
Per Week

Palm Bay Club G46 Siesta Key Fl, Heated Pool, Gulf Front,...

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

$575 - $1795
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

$642 - $1499
Per Week

Apr 27 - 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

Apr 23 - Oct 1   20% off September excluding labor day. Enter promo ...

6144 Midnight Pass Rd 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 - $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

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

6142 Midnight Pass Rd 13N

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

$206 - $314
Per Night

$1442 - $2198
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 14 - Oct 1   20% September rentals excluding Labor Day - enter p ...

6148 Midnight Pass Rd 5S

Siesta Key
Spectacular view on Crescent Beach, Siesta Key florida. This 3rd floor unit is located directly on t...
Condo 2 / 2 / 4

$206 - $314
Per Night

$1442 - $2198
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

$529 - $1249
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

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