Siesta Key Vacation Rental Getaways


Refine Your Search
Check-In 
calendar

Check-Out
calendar
  • Property Options
  • Amenities
  • Location Type
  • Bed
  • Bath
  • Sleeps
Max Price Per Week $
  • Special Offers
  • Online Booking
  • Home/Villa
  • Cottage/Cabin
  • Condo/Townhome
  • Bed & Breakfast
  • Apt/Room/Suite
  • Air Conditioning
  • Washer/Dryer
  • Full Kitchen
  • Satellite/Cable TV
  • Handicap Access
  • High Speed Internet
  • Elevator
  • Maid Service
  • Garage Parking
  • Pets Allowed
  • Private Pool
  • Pool Access
  • Hot Tub
  • Fireplace
  • Smoking allowed
  • Beach Access
  • Beach Front
  • Golf on site
  • Golf nearby
  • Ocean Front
  • Ocean View
  • Lake Front
  • Lake View
  • Ski in/out
  • Walk to Slopes
  • Skiing nearby
 
Sort by: Type BR/BA/Sleeps Price

Island House Beach Resort V22

Siesta Key
Island House Beach Resort - Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 1 1/2 bath v...
Villa 2 / 1.5 / 6

$157 - $240
Per Night

$1099 - $1680
Per Week

Mar 13 - Jan 31   20% off January stays - enter promo code 2017

Island House Beach Resort 6S

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

$194 - $290
Per Night

$1358 - $2030
Per Week

Mar 13 - Jan 31   20% off January stays - enter promo code 2017

Island House Beach Resort 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

$213 - $323
Per Night

$1491 - $2261
Per Week

Gulf & Bay Club: Bayside, 2 Bedrooms, Ground Floor, 2 Poo...

Siesta Key
Just steps from the bay, our newly remodeled condo in a gated Key West-style community is the perfec...
Condo 2 / 2 / 6

*
Online booking available

$114 - $550
Per Night

$795 - $2495
Per Week

Mar 13 - Jan 31   20% off January stays - enter promo code 2017

Island House Beach Resort 4S

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

$213 - $323
Per Night

$1491 - $2261
Per Week

Apr 2 - Jan 31   20% off January 2017 stays, enter promo code 2017

Island House Beach Resort V25

Siesta Key
Island House Beach Resort - Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 1 1/2 bath v...
Villa 2 / 1.5 / 6

$157 - $240
Per Night

$1099 - $1680
Per Week

Beach Place Unit B, 2 Bedrooms, Gulf Front, Ground Floor,...

Siesta Key
Located on what is often described as “the most beautiful beach in America”, Beach Place Unit B is a...
Condo 2 / 2 / 4

*
Online booking available

$214 - $500
Per Night

$1344 - $2525
Per Week

Apr 2 - Jan 31   20% off January 2017 stays, enter promo code 2017

Island House Beach Resort V34

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

$165 - $248
Per Night

$1155 - $1736
Per Week

Apr 2 - Jan 31   20% off January 2017 stays, enter promo code 2017

Island House Beach Resort V39

Siesta Key
Island House Beach Resort, Siesta key, Crescent Beach!New improvements in 2014! 60" tv and ente...
Villa 2 / 2 / 4

$165 - $248
Per Night

$1155 - $1736
Per Week

Bay Tree Club 206C, 2 Bedrooms, 2nd Floor, 2 Heated Pools...

Siesta Key
14 day minimum stay required. Imagine waking up in the morning knowing that a quiet Siesta Key beach...
Condo 2 / 2 / 4

*
Online booking available

$107 - $291
Per Night

$630 - $1999
Per Week

Mar 13 - Jan 31   20% off January stays - enter promo code 2017

Island House Beach Resort 10S

Siesta Key
Island House Beach Resort! Siesta Key Florida, Crescent Beach. Ground floor unit. This 2 bedroom, 2 ...
Condo 2 / 2 / 4

$213 - $323
Per Night

$1491 - $2261
Per Week

Twin Palms 5, 1 Bedroom, Ground Floor, Heated Pool, Wifi,...

Siesta Key
You’ll be just a one-block walk from Siesta Key, the #1 rated beach in the USA, when you stay at Twi...
Condo 1 / 1 / 4

*
Online booking available

$99 - $500
Per Night

$584 - $2195
Per Week

Casa Siesta, ground floor, 2 BRs, walk to Siesta Key beach

Siesta Key
Please note these Check-in Day Requirements for this property: Nov 05 2016 - Dec 23 2016 : Saturday ...
Condo 2 / 1 / 4

*
Online booking available

$130 - $520
Per Night

$910 - $2695
Per Week

Apr 2 - Jan 31   20% off January 2017 stays, enter promo code 2017

Island House Beach Resort V32

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

$165 - $248
Per Night

$1155 - $1736
Per Week

Siesta Dunes Beach 201, 2 Bedrooms, Large Heated Pool, Sp...

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

$114 - $550
Per Night

$668 - $2495
Per Week

Apr 2 - Jan 31   20% off January 2017 stays, enter promo code 2017

Island House Beach Resort V37

Siesta Key
Island House Beach Resort- Siesta Key Florida, Crescent Beach - The lovely villa is located on the w...
Villa 2 / 2 / 6

$165 - $248
Per Night

$1155 - $1736
Per Week

Casa de Mariposa 5542, 3 Bedroom, Gulfview, Elevator, Hea...

Siesta Key
Casa de Mariposa 5542 is a beautifully designed 3 bedroom, 3 bathroom home with a gulf view, heated ...
Home 3 / 3 / 8

*
Online booking available

$318 - $850
Per Night

$2096 - $4500
Per Week

Mar 13 - Jan 31   20% off January stays - enter promo code 2017

Island House Beach Resort 11S

Siesta Key
This luxury apartment is part of Island House Beach Resort, which is located on 280 ft. of the award...
Condo 2 / 2 / 4

$213 - $323
Per Night

$1491 - $2261
Per Week

Apr 2 - Jan 31   20% off January 2017 stays, enter promo code 2017

Island House Beach Resort V3

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

$165 - $248
Per Night

$1155 - $1736
Per Week

Castaway Cove 3B, 2 Bedrooms, Lagoon View, Wifi, Sleeps 5

Siesta Key
With beautiful lagoon views from both the big lanai and the master bedroom, our condo at Castaway Co...
Condo 2 / 2 / 5

*
Online booking available

$71 - $300
Per Night

$416 - $1695
Per Week

Apr 2 - Jan 31   20% off January 2017 stays - enter promo code 2017

Island House Beach Resort V10A

Siesta Key
Island House Beach Resort - Siesta Key Florida, Crescent Beach. This 2 bedroom, 2 bath duplex is loc...
Villa 2 / 2 / 6

$153 - $237
Per Night

$1071 - $1659
Per Week

Gulf and Bay Club 102B, 2 Bedrooms, Beach Front, Ground F...

Siesta Key
Love sunsets? How about white sand, plush beds, a choice of three pools, swans ... and a little shuf...
Condo 2 / 2 / 6

*
Online booking available

Contact
Owner
Directly
For Rates

Gulf and Bay Club 305C, 2 Bedrooms, 3 pools, Gym, Spa, Wi...

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

Contact
Owner
Directly
For Rates

Mar 13 - Jan 31   20% off January stays - enter promo code 2017

Island House Beach Resort 9N

Siesta Key
Island House Beach Resort! Siesta Key Florida, Crescent Beach. Ground floor unit. This 2 bedroom, 2 ...
Condo 2 / 2 / 6

$213 - $323
Per Night

$1491 - $2261
Per Week

Apr 2 - Jan 31   20% off January 2017 stays – enter promo code 2017

Island House Beach Resort V10B

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

$139 - $216
Per Night

$973 - $1512
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