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Vacation Rentals & Beach Rentals in Siesta Key

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1,100 beach rentals

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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$189

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. 36 minutes

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$200

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 32 minutes

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$139

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

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$287

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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$290

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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$172

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.

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$164

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 16 minutes

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$196

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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$195

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 29 minutes

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$162

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. 3 minutes

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$110

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. 36 minutes

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$285

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. 37 minutes

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$126

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. 3 minutes

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$106

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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$549

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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$174

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$121

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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$284

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

Siesta Key apartment

3 bedrooms / 3 bathrooms / sleeps 8

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$139

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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$502

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

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$251

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

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$178

Charming Siesta Key Condo, Walk to Beach, Pool

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 38 minutes

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Price per night from

$108

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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$126

Chinaberry 436 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

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$239

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

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$126

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 25 minutes

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$212

Large community heated pool...grab one of the provided beach towels and head on

Siesta Key condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 minutes

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$101

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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$108

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

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$200

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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$149

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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$286

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.

Responds fast! avg. 1 hour 50 minutes

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$141

Heated Pool w/ Short Walk to Beach, Renovated & Updated, Fishing Pier, Tennis, L

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 minutes

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$118

Firethorn 320 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$236

Viewing 37 of 1,100
rentals in Siesta Key

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