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Vacation Rentals & Beach Rentals in Siesta Key

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1,079 beach rentals

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. 1 hour 23 minutes

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$149

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

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$177

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

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$141

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

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$289

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

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$287

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

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 5

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$168

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 24 minutes

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$163

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

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$188

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. 1 hour 23 minutes

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$149

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. 1 hour 26 minutes

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$160

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$115

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

Siesta Key cottage

1 bedroom / 1 bathroom / sleeps 4

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$171

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

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$268

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

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$133

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

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 6

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$95

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

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

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$228

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

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 8

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$182

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$116

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

Siesta Key house

4 bedrooms / 3 bathrooms / sleeps 6

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$255

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

Siesta Key apartment

3 bedrooms / 3 bathrooms / sleeps 8

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$169

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

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 8

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$206

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

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 8 minutes

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$205

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 55 minutes

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$197

Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.

Responds fast! avg. 1 hour 29 minutes

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$160

Charming Siesta Key Condo, Walk to Beach, Pool

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 1 hour 44 minutes

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Price per night from

$117

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.

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$103

Holiday House 1

Siesta Key apartment

1 bedroom / 1 bathroom / sleeps 4

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$90

Chinaberry 436 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

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$226

Seagrove

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$126

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

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$132

5 Bedroom Beachfront Home on Siesta Beach!! 49 Beach Rd

Siesta Key house

5 bedrooms / 3 bathrooms / sleeps 10

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$672

Recently updated, Crescent Beach resort, Heated Pool, Jacuzzi, Tennis, Barbeques

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 9 minutes

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$213

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$111

LuLu's Leatherback Walk to Beach & Village, Heated Pool, WiFi, Barbecue Station,

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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$195

Private Beach, Full Gulf Views, Wifi/Cable, Heated Swimming Pool Overlooking Oce

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$198

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$156

The Shells Villa - Next to Beach & Village

Siesta Key house

3 bedrooms / 3 bathrooms / sleeps 10

“Great Experience and Location!” We could not have been happier with our Experience at Shell Villa. Location to the Village was super close as described. Access to the beach was great both through the private walkway or the public access about two block away. The house was well stocked and the floor plan was perfect for our two families. Best place I have rented on SK in 5 years.

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$261

Beachfront- Gulf View! 2 BR/BA Crescent Arms 603S, #1 Beach in the US.

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 36 minutes

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Price per night from

$179

Viewing 38 of 1,079
rentals in Siesta Key

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