Siesta Key Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price
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

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

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

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 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

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

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

May 23 - 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

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

6150 Midnight Pass Rd V5

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

$160 - $241
Per Night

$1120 - $1687
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 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

May 30 - Oct 1   20% September rentals excluding Labor Day, enter pr ...

6150 Midnight Pass Rd V33

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

$160 - $241
Per Night

$1120 - $1687
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

Apr 27 - Oct 1   20% September rentals excluding Labor Day, enter pr ...

6150 Midnight Pass Rd V7

Siesta Key
Island House Beach Resort, Crescent Beach, Siesta Key Florida! Newly renovated 2 bedroom, 2 bath uni...
Villa 2 / 2 / 6

$160 - $241
Per Night

$1120 - $1687
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

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

$125 - $350
Per Night

$575 - $1595
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

Jun 1 - 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

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

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

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

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

6150 Midnight Pass Rd V35

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

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