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Siesta Key Rentals with Pools

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1,036 beach rentals in Siesta Key with pools

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

Match: Swimming pool

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Price per night from

$152

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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Price per night from

$140

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

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Price per night from

$107

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$288

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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Price per night from

$287

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

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Price per night from

$169

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!!

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Price per night from

$147

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

Match: Swimming pool

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Price per night from

$162

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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Price per night from

$189

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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Price per night from

$151

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

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Price per night from

$119

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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Price per night from

$133

goldeneye luxury private family plantation house

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$316

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

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Price per night from

$95

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

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Price per night from

$182

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

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Price per night from

$116

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

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Price per night from

$255

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$277

The Perfect 2Bedroom/2Bath Steps Away From Siesta Key Beach- BiancoSands

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$238

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. 1 hour 22 minutes

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Price per night from

$216

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

Siesta Key apartment

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 minutes

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Price per night from

$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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Price per night from

$205

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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Price per night from

$206

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

Match: Swimming pool

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Price per night from

$199

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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Price per night from

$163

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.

Match: Swimming pool

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Price per night from

$103

Chinaberry 436 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$227

Seagrove

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$126

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

Match: Swimming pool

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Price per night from

$132

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 0 minutes

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Price per night from

$211

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

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Price per night from

$113

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

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Price per night from

$111

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

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 minutes

Match: Swimming pool

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Price per night from

$195

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 minutes

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Price per night from

$198

Responds fast! avg. 3 minutes

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Price per night from

$156

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. 37 minutes

Match: Swimming pool

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Price per night from

$180

Luxurious 2 BR Condo - Short Walk to Siesta Beach

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

“a fine 2 weeks in Siesta” charming property, that was comfortable for four. The unit was very clean and fresh upon arrival. The neighbours were friendly and the overall property well kept. Siesta Key is a quiet community with usual shopping amenities over the causeway. This property was a brief 10 minute walk to the beach. Would we stay again, yes.

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Price per night from

$141

Viewing 38 of 1,036
rentals in Siesta Key

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