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Vacation Rentals & Beach Rentals in Siesta Key

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1,714 beach rentals

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 available when we needed them. What was great was that we had all beach items available to us and were very useful. We were in close proximity to everything and the beach and restaurants were great! Everyone in the area was very friendly and my husband and I want to definitely come back!

Responds fast! avg. 1 hour 29 minutes

Price per night from

$178

WE LIKE BLUE, SIESTA BLUE! 2 BED BAYSIDE CONDO ON SIESTA KEY

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. It's located right in the middle of the island so it was only a short drive to amazing restaurants and the beautiful Siesta Beach. The condo itself was lovely, modernly updated and had everything we needed to make it our home away from home. My toddler constantly asks when we'll go back to our "little house", and I am happy to tell him that we will be back next year!

Responds fast! avg. 2 hours 16 minutes

Price per night from

$141

Walk to the beach from this adorable condo. Beachside. Perfect location. Bikes,

Siesta Key house

1 bedroom / 1 bathroom / sleeps 2

“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 have wanted -- a very short and easy walk to beach access 13, Point of Rocks, and many restaurants (aaaaand the liquor store), a very comfortable bed with the appropriate amount of pillows (EIGHT), a fully equipped kitchen with everything we needed to eat in when we wanted, a large covered porch, and everything was CLEAN. Angel was a fantastic host -- quick to respond and clear and concise with his communication. The price was more than right. I cannot say enough great things about this property and Angel. Recommended so very highly.

Responds fast! avg. 43 minutes

Price per night from

$160

Siesta Key Villa A - Only 150 yards to Crescent Beach and heated pool!

Siesta Key villa

2 bedrooms / 1 bathroom / sleeps 4

“This place was absolutely perfect!” This place was amazing. We stayed here just a week:( but we will definitely be back. The condo was clean, fully equipped, comfortable and perfectly located. The beautiful beach was a very short walk away and the lovely heated pool was even closer. I came here with 2 of my daughters 18 and 22. They loved it also. The restaurant “ The Toastd Mango” right across the street had delicious omelettes and friendly staff. The trolley stop is also right across the street and it takes you into the village. And back free! So park your car because everything is right here:) ENJOY

Responds fast! avg. 2 hours 31 minutes

Price per night from

$151

Siesta Key- Beach Chic Retreat, Siesta Key 3 Bedroom 2 Bath Apartment

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 7

“This was the definition of home away from home” great value for your money...very cozy, with lots of new upgrades. Easy access to the beach and restaurants.

Responds fast! avg. 1 hour 29 minutes

Price per night from

$269

Siesta Key Villa B - Only 150 yds. to Crescent Beach and heated pool!

Siesta Key villa

2 bedrooms / 1 bathroom / sleeps 4

“Another great stay!” Location is great and owners are awesome to work with! Clean and fully furnished! Thanks for another great stay Derek and Marina! Look forward to next time!

Responds fast! avg. 2 hours 31 minutes

Price per night from

$150

Remodeled 2br 2ba with private patio, beautiful water views, walk to #1 beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 11 minutes

Price per night from

$109

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

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

“Awesome Condo Unit” There were 4 in our party and nothing that we were disappointed with. We absolutely loved every moment!! We will definitely rent this unit again!!

Price per night from

$147

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$297

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. 3 minutes

Price per night from

$287

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$191

Jamaica Royale #100-Peaceful Gulf Side Condo

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 48 minutes

Price per night from

$198

Beachfront Getaway in Siesta Key

Siesta Key townhouse

1 bedroom / 1 bathroom / sleeps 4

“Very comfortable, nice amenities and well run.” Loved the beach and the nearby restaurants. The free trolly ride was easy to use and a great way to go into the village.

Responds fast! avg. 53 minutes

Price per night from

$216

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

Responds fast! avg. 2 hours 37 minutes

Price per night from

$135

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. 3 minutes

Price per night from

$105

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 vacation we ever had.

Price per night from

$119

WHAT A VIEW !! 2 BED BAYSIDE CONDO ON SIESTA KEY

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 and dryer in unit. The layout of this rental was spacious,the bed was very comfortable I slept like a baby which is rare when I'm away from home.The view of the intercostal water way and tropical landscaping were breathtaking whether relaxing in living room or dinning.It was very peaceful ,walking distance to Siesta keys famous beach and close to all amenities. Would recommend Bay Oaks!Thanks Barbara Okin.

Responds fast! avg. 2 hours 16 minutes

Price per night from

$167

Across the street from Siesta Key Beach, Gulf View, Pool, Tennis, Parking, Balco

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 minutes

Price per night from

$155

Siesta Key Beach w/ Partial Gulf Views Across the Street, Renovated, Overlooks H

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 minutes

Price per night from

$116

Complex on the Bay, Walk to Beaches, Wifi, Ground Floor, Renovated, Enclosed Pat

Siesta Key condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 minutes

Price per night from

$113

Siesta Key Condo w/Private Beach Access, Wifi Included, Heated Pool, Tennis & B

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 minutes

Price per night from

$126

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. 3 minutes

Price per night from

$113

3 Bedroom/ 2 Bath unit across from Siesta Key Beach Access.- Islamorada

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$205

goldeneye luxury private family plantation house

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$330

"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

$171

Seagrove

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$126

Holiday House 1

Siesta Key apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$126

Perfect Getaway-2Bedroom/2Bath Steps from Beach with Pool Access!!- La Estrella

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$228

Best Deals on Siesta Key

Siesta Key apartment

1 bedroom / 1 bathroom / sleeps 4

“Nice and easy to get around” You have a wonderful neighbor. I was able to access all the amenities you described. Navigated through out the area with ease.

Price per night from

$107

Canal Home on Siesta Key w/ Pool, Wifi, Renovated 1950 Style Sarasota School of

Siesta Key house

4 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 minutes

Price per night from

$255

Fido Friendly, Saltwater Pool, Only 1 mile to SK Beach, Close to the Village, Sh

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 minutes

Price per night from

$182

Luxury Villa, Sleeps 6 Comfortably Located on Siesta Key Beach, Sarasota Florida

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 52 minutes

Price per night from

$207

Charming Siesta Key Condo, Walk to Beach, Pool

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 1 hour 44 minutes

Price per night from

$117

Walk to Siesta Beach, Heated Pool, Wifi, Fido friendly, Renovated Ground Floor U

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 minutes

Price per night from

$118

Sea Club II

Siesta Key condo

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$113

Luxury Condo Ground Floor Across the Street

Siesta Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$182

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

Price per night from

$277

Beautifully Renovated & Modern, Wifi, Harbor Towers, 3 bedroom with den

Siesta Key apartment

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 minutes

Price per night from

$139

Viewing 38 of 1,714
rentals in Siesta Key

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About Siesta Key

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

Top Destination reviews

#1 Beach - "Super Clean" - 2 Level Townhouse - 1400sf 2Br/2.5 Bth- 5 Star Rating
Great stay in Sarasota

My husband and our two daughters spent a wonderful four days in Sarasota. The townhome we stayed in was beautiful and had all the amenities we needed. We spent every day at the beach and relaxed at the townhome in the evenings. We would definitely stay here again and have recommended this place to our family and friends. Thanks Louie!see more
Peaceful Haven on Siesta Key with Beach Access
Tropical paradise! Perfect condo for family vacay!

Midnight Cove II is perfectly situated in the center of Siesta Key! The Village is just a short drive north and Turtle Beach is an equally short drive south. It is within walking distance of many restaurants, shops and attractions. Beach access is just a short walk across the street. The grounds are well-maintained and the staff is super friendly and helpful. Great pool area, too! I will definitely be back.see more
Siesta Key Villa A - Only 150 yards to Crescent Beach and heated pool!
Awesome owners and location

The location is great, only 3 minutes walking to a private beach. The house offers all the essentials you might need. This is our second time stay and we were not dissapointed again. The owners are very responsive and helpful. … see more
Our House at the Beach C-207 Sunny Southern View Close to Pool
Christmas vacation 2019

The house was very clean and well kept. We immensely enjoyed our stay over the Christmas week, the beach is within a 5 minute walk. The only complaint we had is that there were only 3 washcloths for the 6 people we had staying there. We would definitely stay there again! … see more
Palm Bay on Private Beach w/Private Access, Full Beach Views from 7th Fl, Pool
Great condo

Loved it. Modern, beachy, clean, well equipped. Excellent location on the beach. Would definitely stay again. … see more
WE LIKE BLUE, SIESTA BLUE! 2 BED BAYSIDE CONDO ON SIESTA KEY
Considering the Corona Influences It Was A Nice Stay

We stayed on Siesta Key and other than the traffic it's a lovely area. We were to stay 3 weeks but actually returned a week early since we were so concerned with the health risks. There were a number of nice sea-food restaurants where we stayed which we enjoyed the first week we were there until we began social distancing. The condo altho fairly small was confortable and the complex very quiet.see more

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