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Siesta Key Rentals with Pools

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1,055 beach rentals in Siesta Key with pools

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

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 4

“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.

Responds fast! avg. 3 hours 25 minutes

Match: Swimming pool

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Price per night from

$139

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

Siesta Key villa

2 bedrooms / 1 bathroom / sleeps 4

“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.

Responds fast! avg. 29 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. 29 minutes

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Price per night from

$195

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. 1 hour 51 minutes

Travelers’ Choice award

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Price per night from

$114

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!!

Responds fast! avg. 3 hours 57 minutes

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Price per night from

$147

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. 4 minutes

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Price per night from

$290

Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 19 minutes

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Price per night from

$196

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. 2 hours 6 minutes

Match: Swimming pool

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Price per night from

$251

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 24 minutes

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Price per night from

$327

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. 3 hours 6 minutes

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Price per night from

$127

Walk to Beach, Wifi, Water view from patio, Heated Pool, On Trolley Line

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 4 minutes

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Price per night from

$115

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. 3 hours 25 minutes

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Price per night from

$165

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. 4 minutes

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Price per night from

$177

Siesta Key Beach is Across the Street, Partial Bay Views, WiFi, Renovated, Overl

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 4 minutes

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Price per night from

$124

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. 4 minutes

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Price per night from

$117

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. 4 minutes

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Price per night from

$136

Only 6 Minute Walk to Crescent Beach, Free Wifi, Private Lanai, Heated Pool, Fis

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 4 minutes

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Price per night from

$111

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

$251

Seagrove

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$127

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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Price per night from

$103

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. 4 minutes

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Price per night from

$271

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. 4 minutes

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Price per night from

$174

Charming Siesta Key Condo, Walk to Beach, Pool

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 1 hour 57 minutes

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Price per night from

$114

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. 4 minutes

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Price per night from

$119

Luxury Condo Ground Floor Across the Street

Siesta Key house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$180

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 22 minutes

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Price per night from

$246

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

Siesta Key apartment

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 4 minutes

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Price per night from

$156

Chinaberry 436 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$227

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 31 minutes

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Price per night from

$212

Responds fast! avg. 4 minutes

Match: Swimming pool

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Price per night from

$156

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

$286

Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front

Siesta Key house

2 bedrooms / 2 bathrooms / sleeps 6

“What a great view” We usually rent a house one block from the main Siesta Key beach area. This year friends rented the house and my husband and I stayed in this condo for a week. Loved the view of the beach from the living room! Loved the lani! Location was great. Pool was massive compared to our usual house pool, however we did have to walk thru parking lot to get there. The noise from the hall was annoying. And I did miss my temperpedic mattress, but had a great relaxing time.

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Price per night from

$222

Beach Walk Townhouse

Siesta Key townhouse

3 bedrooms / 3 bathrooms / sleeps 6

“Great vacation and Great Accomations” We loved the accommodations. Great location close to beach access and to the village.The pool was wonderful with lovely landscaping. The house was spacious and very clean. Virginia the manager was also great! We would definitely stay here again.

Responds fast! avg. 28 minutes

Match: Swimming pool

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Price per night from

$265

Buttonwood 462 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$243

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 19 minutes

Match: Swimming pool

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Price per night from

$178

Siesta Key Condo, Crescent Arms, unit 605 South

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 48 minutes

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Price per night from

$217

Viewing 37 of 1,055
rentals in Siesta Key

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