Siesta Key Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

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

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

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

6150 Midnight Pass Rd V40b

Siesta Key
Island House Beach Resort! Siesta Key Florida - Crescent Beach. The 2 bedroom, 1 bath villa is 1000 ...
Villa 2 / 1 / 4

$146 - $218
Per Night

$1022 - $1526
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

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

6150 Midnight Pass Road V4

Siesta Key
Island House Beach Resort - Siesta Key Florida, Crescent Beach - This lovely 2 bedroom, 1 bath villa...
Villa 2 / 1 / 6

$146 - $218
Per Night

$1022 - $1526
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

Feb 2 - 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 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

Feb 21 - Oct 1   20% September rentals excluding Labor Day, enter pr ...

6150 Midnight Pass Rd V28

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

$160 - $241
Per Night

$1120 - $1687
Per Week

May 7 - Oct 1   20% Septermber rentals excluding Labor Day - enter ...

6146 Midnight Pass Rd 9S

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

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

Feb 12 - 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

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

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

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

May 18 - 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

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

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

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

6144 Midnight Pass Rd 4N

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

$206 - $314
Per Night

$1442 - $2198
Per Week

Mar 21 - Nov 1   20% off September rentals excluding Labor Day - ent ...

6142 Midnight Pass Rd 15N

Siesta Key
Island House Beach Resort! Crescent Beach, Siesta Key Florida. This 1300 sq. ft. apt. is located on ...
Condo 2 / 2 / 4

$206 - $314
Per Night

$1442 - $2198
Per Week

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

6150 Midnight Pass Rd V39

Siesta Key
Island House Beach Resort, Siesta key, Crescent Beach! Professionally decorated in October 2011. Thi...
Villa 2 / 2 / 6

$160 - $241
Per Night

$1120 - $1687
Per Week

Mar 7 - Oct 1   20% Septermber rentals excluding Labor Day, enter p ...

6150 Midnight Pass Rd 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 - $241
Per Night

$1120 - $1687
Per Week

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

6150 Midnight Pass Rd V25

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

$152 - $232
Per Night

$1064 - $1624
Per Week

Siesta Key Gulf and Bay 207F Beach Front, 3 pools, fitnes...

Siesta Key
A large and comfortable condo, Siesta Key Gulf and Bay 207 rentals boasts 1,525 square feet of Medit...
Condo 2 / 2 / 6

*
Online booking available

$564 - $1750
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