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Vacation Rentals & Beach Rentals in Siesta Key

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1,012 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. 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

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

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- 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

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

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 14 minutes

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$114

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

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$287

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

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

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 34 minutes

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$327

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

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

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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$172

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. 3 minutes

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$121

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

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

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

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

Holiday House 1

Siesta Key apartment

1 bedroom / 1 bathroom / sleeps 4

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$126

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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Price per night from

$549

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

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

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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$174

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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$108

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

$108

Sea Club II

Siesta Key condo

2 bedrooms / 1 bathroom / sleeps 5

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$114

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 30 minutes

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$245

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

$139

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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Price per night from

$212

Beautiful, Affordable Close to famous Siesta Beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 4

“It was wonderful!” Everything about the trip and condo was great! Mike met us to give us the keys and we called him for suggestions about restaurants, etc. and he was very helpful. The condo was very clean and had everything we needed. It was also great that we were able to use the beach chairs and umbrella. I am already trying to figure out when we can go again.

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$162

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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Price per night from

$286

Responds fast! avg. 3 minutes

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$149

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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$221

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

Siesta Key Condo, Crescent Arms, unit 605 South

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 50 minutes

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$229

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

Viewing 37 of 1,012
rentals in Siesta Key

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