Siesta Key Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

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

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

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

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

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

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

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 Dunes Beach 201, 2nd Floor, Spa, Large Heated Pool...

Siesta Key
Decked in pure tropical style, Siesta Dunes Beach 201 in Siesta Key, Florida is an ideal choice for ...
Condo 2 / 2 / 6

*
Online booking available

$125 - $350
Per Night

$564 - $1595
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

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

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

House of Sun 307 Siesta Key, Large Heated Pool, Gulf View...

Siesta Key
Siesta Key Florida House of Sun 307 rentals condos is very family-friendly, was recently renovated a...
Condo 2 / 2 / 6

*
Online booking available

$146 - $450
Per Night

$750 - $2095
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 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

May 28 - Oct 1   20% September rentals excluding Labor Day, enter pr ...

6150 Midnight Pass Rd V8

Siesta Key
Island House Beach Resort - Siesta Key Florida, Crescent Beach. This bright spacious villa is approx...
Villa 2 / 2 / 6

$152 - $232
Per Night

$1064 - $1624
Per Week

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

6150 Midnight Pass Rd V34

Siesta Key
Island House Beach Resort, Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 1 1/2 bath vi...
Villa 2 / 2 / 4

$152 - $232
Per Night

$1064 - $1624
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

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

6150 Midnight Pass Rd V22

Siesta Key
Island House Beach Resort - Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 1 1/2 bath v...
Villa 2 / 2 / 6

$152 - $232
Per Night

$1064 - $1624
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

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

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

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

6150 Midnight Pass Rd V36

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

$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

May 30 - 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 25 - Oct 1   20% September rentals excluding Labor Day, enter pr ...

6150 Midnight Pass Rd V40a

Siesta Key
Island House Beach Resort! Siesta Key Florida - Crescent Beach. Completly remodeled January 2011!! T...
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.

More Getaway Locations and Properties