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Vacation Rentals & Beach Rentals in Siesta Key

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Vacation Rentals & Beach Rentals in Siesta Key

About Siesta Key

2,831 beach rentals

We like Blue,Siesta Blue! Cert.of Excellence 2014

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 4

“Absolutely Wonderful” We stayed the second week of September at Bay Oaks Condos, and it was absolutely WONDERFUL! We basically had the run of the condo to ourselves, including the swimming pool, which was the only place my toddler wanted to hang out.

Price per night from

$122

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Siesta Key 2 Bedroom 1 Bath Modern/Contemporary Decor Apartment

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 5

“Amazing!” I stayed here with my husband and we had a great time! We were in Orlando visiting family and we decided to arrange some us time. The condo was excellent and very clean! Kathy and her husband were very informative, respond quickly,and avail

Responds fast! avg. 1 hour 18 minutes

Price per night from

$156

1 / 16

Island House Beach Resort V9

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

“Our vacation at Siesta Key was as always relaxing and enjoyable.” Villa 9 was newly redecorated; therefore, it was a pleasure to spend 10 days in a clean, updated, and comfortable villa. The comfort of Villa 9 was worth a little bit of a walk to the

Price per night from

$175

1 / 16

Island House Beach Resort V25

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

“Spring break” Loved the location. Place was very nice for a family of 6.. The pool was warm , staff was very helpful and nice , beach was super close..

Price per night from

$175

1 / 17

2Bedroom/ 2Bath Condo Across From Siesta Key Beach With The Best View!!-OHAB 601

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$170

1 / 11

Island House Beach Resort V5

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

“Great location and lovely accommodations!” This was our second year to vacation here and we plan to return next year! It is so close to the beautiful beach. Our experiences have been very relaxing and worth repeating.

Price per night from

$175

1 / 16

*Special Dec 8th to 23rd $65/ngt *Jan Special only $75/ night* # 1 beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 35 minutes

Price per night from

$86

1 / 45

2 Bedroom Beachfront Home on Siesta Beach!! Directly on the beach!! 47 Beach Rd

Siesta Key townhouse

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$251

1 / 25

Island House Beach Resort 14N

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Great getaway!” Our family enjoyed a long weekend around Labor Day weekend at Island House. We have stayed at Island House before and always have a good time. Fabulous beach, helpful staff, relaxing place to be. This was our first time staying in 14

Price per night from

$227

1 / 20

Only 150 yards to Crescent Beach and heated pool!

Siesta Key villa

2 bedrooms / 1 bathroom / sleeps 4

“Amazing Rental” This rental was roomier than expected! Everything was perfect! The pool and beach is so close, also there is some local restaurants and shops so close by! Couldn't have asked for better!

Price per night from

$90

1 / 58

Quiet and Comfortable Condo Near Turtle Beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 5

“Siesta sweet spot” Great value for location. Nice pool, visits with the manitees. Close to everything. This time of year ocean water was amazing

Price per night from

$95

1 / 42

Island House Beach Resort V39

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$175

1 / 17

Island Time Rentals is ready to host our winter friends. Stay warm with us.

Siesta Key house

1 bedroom / 1 bathroom / sleeps 4

“Book with Island Time!” We really lucked out with our first Flipkey booking. My husband and I traveled to Siesta Key last year for our honeymoon, and we returned this year to celebrate our anniversary. The property had everything we could possibly hav

Price per night from

$120

1 / 14

Top Floor End Unit Directly Across the Street from Siesta Key public beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$122

1 / 10

What a View!! 2/2 Cert. of Excellence Winner 2014

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Beautiful and memorable vacation with our son,wife and grandchil” My husband and I rented unit B41,it was beautifull, tastefully decorated stainless steel appliances and new furniture. The owners thought of everything.Very pleased to have a washer an

Price per night from

$144

1 / 28

Island House Beach Resort 12S

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$227

1 / 14

Gulf Side Siesta Key Villa~Peaceful 1st Floor Villa, 3 pools-Jamaica Royale #100

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

“Spring break” This unit was beautifully done; recently renovated, impeccably clean and very close to the beach! The owner was e trendy helpful and accommodating. She made it easy and if you are headed to Siesta Key, you must stay here!

Responds fast! avg. 1 hour 43 minutes

Price per night from

$156

1 / 47

"Cottage by the Sea" 1 Bedroom/ 1 Bath Across From Beach!!- · 3031, 3032

Siesta Key cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$120

1 / 14

Gorgeous Direct gulf Front 2 Bedroom Condo on Siesta Keys... JUST REMODELLED

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 4 minutes

Price per night from

$160

1 / 52

Walk to Siesta Key Beach, Wifi Included in this Private Villa, Heated Pool & Com

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 8 minutes

Price per night from

$131

1 / 36

The Top Siesta Key Location, The Village Studio - Eat Shop Beach!

Siesta Key cottage

1 bedroom / 1 bathroom / sleeps 2

“Best of the village and the beach!” Great location! Steps from Siesta Key Village with great resteraunts, shops and clubs. Beach Access 4 is just across the street and we were from the front door to the water in under 10 minutes! Beautiful beach and s

Responds fast! avg. 43 minutes

Price per night from

$100

1 / 32

Island House Beach Resort 4S

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

“A wonderful family vacation!” We loved our stay at the Island House! The staff and property were excellent! The rental unit was perfect! the view was amazing and the pool/club house made for an ideal family trip. My children and I would love to go

Price per night from

$227

1 / 20

Island House Beach Resort 3N

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Relax and chill out” We have stayed at this apartment twice once in 2005 and 2008 after Island house was recommended to us by friends, the first time we stayed we all fell in love with Siesta keys and island house, and when we visited again we asked t

Price per night from

$227

1 / 16

Gulf Beach, Pool And Walk To Siesta Key Village

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Gulf Beach, Pool And Walk To Siesta Key Village” We had the best time ever. Nice being able to wLk to village. Sunsets are beautiful. Dolphin hanging out at the pier Beaches are near. The pool is next door. Condo is very clean and great Best

Responds fast! avg. 3 hours 54 minutes

Price per night from

$101

1 / 36

Brand New, Walk to Beach, Wifi, Water view from patio, Heated Pool, On Trolley L

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 8 minutes

Price per night from

$91

1 / 36

Jamaica Royale #92 on the #1 Beach in the USA!

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 50 minutes

Price per night from

$253

1 / 12

Only 150 yrds to Siesta Key Beach and heated pool!

Siesta Key villa

2 bedrooms / 1 bathroom / sleeps 4

“I have found my happy place!” Enjoyed our recent stay here. Very comfortable and clean accomodations. I have a Tempurpedic mattress at home so that was one of the reasons I booked here. Couch in living room was also comfortable. Did not get to try

Price per night from

$90

1 / 50

600 ft. to Shell Beach, Pool/Spa, Fire Pit, New & Custom Nantucket Style Home,

Siesta Key house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 8 minutes

Price per night from

$251

1 / 46

Island House Beach Resort V35

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

“Excellent Villa except for the sofa bed” Absolutely gorgeous place to stay. The Villa was very spacious and comfortable for my family of 6. We went to Sarasota for a graduation and were able to have my family over for a visit from Miami without a prob

Price per night from

$175

1 / 18

NEW Private Siesta Key Vacation Rental Home W/ Heated Pool on Quiet Street

Siesta Key condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$150

1 / 36

Siesta Key Beach w/ Gulf Views Across the Street, Newly Renovated, Patio Overloo

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 8 minutes

Price per night from

$109

1 / 32

Sandy Toes Siesta Key Florida (6796)

Siesta Key house

2 bedrooms / 2 bathrooms / sleeps 6

“Fantastic!!!” Loved it!!! This place was very clean, close enough to beach, very spacious, tastefully decorated with upgrades, decent pool, a manager on site, and more beach gear than you could ask for. ...Chairs, games, rafts, umbrellas, bikes, towe

Responds fast! avg. 56 minutes

Price per night from

$215

1 / 40

Walk to Siesta Key Beach, Heated Pool, Wifi, Renovated Ground Floor Unit With Co

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 8 minutes

Price per night from

$106

1 / 36

Beachfront Getaway in Siesta Key

Siesta Key townhouse

1 bedroom / 1 bathroom / sleeps 4

“Spring Break” Our "beach front getaway" was great! The place was updated and very clean. The furnishings were comfortable and we had everything we needed from kitchen equipment to beach chairs. The area was great! We could walk or ride bikes anywhe

Responds fast! avg. 1 hour 1 minutes

Price per night from

$189

1 / 28

Two Bedroom/ One Bath with Heated Pool and Beach Access at Sea Club 2!!-9E

Siesta Key condo

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$130

1 / 21

goldeneye luxury private family plantation house

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$280

1 / 41

LJ's "Rustic Cottage"-- 2 Bedroom/ 2 Bath Steps From The Sand With Pool Access!!

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$160

1 / 32

Gulf View at Our House At The Beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 8 minutes

Price per night from

$126

1 / 42
Viewing 38 of 2,831

About Siesta Key

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What was once a secret gem known to only a few, has rapidly become America's darling beach town.

Siesta Key, located in Sarasota County and about an hour south of the Tampa Bay Area, is an eight-mile island accessible by two bridges from the mainland. Sandals and swimming suits are accepted - even expected in virtually all of the restaurants and boutiques that populated the island - especially so of those located in Siesta Key Village. The atmosphere is as cool as the white quartz sands in the daytime, and while libations and celebrations can warm up the evening, you are never to far from a tiki-esque style bar and the quiet sounds of ocean waves gliding up and down the beach.

In 2011, Dr. Beach named Siesta Beach No. 1 in the nation for its sugary white sand. Siesta Key beach is, in fact, almost entirely composed of crushed quarts crystal. This unique composition not only makes this sand sparkle under the Florida sun, but also keeps the sand cool on even the hottest of Florida summer days. The sand is perfect for sculpting, and every year Siesta Key is home to world-class sand sculpting competitions.

Despite its popularity, there are still quiet corners of Siesta to sneak off to and explore.

Turtle Beach located at the southern end of Siesta Key has sand that's a bit coarser. This beach is a great fishing and snorkeling hot spot. The beach has a steeper incline and carries more shells. After a storm beachcombers might even find a petrified shark's tooth. Nearby are restaurants, shopping and a few local nightspots.

Crescent Beach is another quieter spot, just south of Siesta Key Beach. Enjoy the same blue waters in a secluded atmosphere. This area contains coral formations and bright marine life - perfect for diving.

Siesta Key is perfectly fit for families, singles, and couples alike. Lodging accommodations can be found throughout the key, including hundreds of vacation rentals. Though active year round, Siesta Key's peak season runs January through April. Plan to book your stay as soon as possible if your vacation is planned within that duration.

Information provided by:Visit Sarasota County

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