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Siesta Key Rentals

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Siesta Key Rentals

544 rentals

NEW EVERYTHING Luxury 1 king Bedroom Villa #4 Siesta Key Pool JAN SPECIALS

Siesta Key apartment

1 bedroom / 1 bathroom / Sleeps 3

$129

1 / 12

Palm Oasis - Relax in Comfort -

Siesta Key house

4 bedrooms / 3 bathrooms / Sleeps 10

$358

1 / 35

Firethorn 510

Siesta Key apartment

2 bedrooms / 1 bathroom / Sleeps 4

$125

1 / 19

Only 150 yrds to Siesta Key Beach and heated pool!

Siesta Key villa

2 bedrooms / 1 bathroom / Sleeps 4

“I have found my happy place!” Enjoyed our recent stay here. Very comfortable and clean accomodations. I have a Tempurpedic mattress at home so that was one of the reasons I booked here. Couch in living room was also comfortable. Did not get to try

$119

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What a View!! 2/2 Cert. of Excellence Winner 2014

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 an

$143

1 / 28

We like Blue,Siesta Blue! Cert.of Excellence 2014

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.

$117

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Siesta Key Townhouse across from Pristine Sand & B

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. T

$155

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Chinaberry 436

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$213

1 / 16

2 North

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

“terrific views” We were very pleased with the clean and spacious condo. We loved being able to see the ocean from our living room. The resort was clean, people were so friendly and we felt very safe. It was comforting to see workers around all hours

$222

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$120

1 / 30

Firethorn 711

Siesta Key apartment

2 bedrooms / 1 bathroom / Sleeps 4

$120

1 / 14

Chinaberry 474

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$220

1 / 26

Beachfront Getaway in Siesta Key

Siesta Key townhouse

1 bedroom / 1 bathroom / Sleeps 4

“Spring Break” Our "beach front getaway" was great! The place was updated and very clean. The furnishings were comfortable and we had everything we needed from kitchen equipment to beach chairs. The area was great! We could walk or ride bikes anywhe

$198

1 / 28

12 South

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$222

1 / 15

Firethorn 514

Siesta Key apartment

2 bedrooms / 1 bathroom / Sleeps 4

$120

1 / 30

Villa 35

Siesta Key villa

2 bedrooms / 2 bathrooms / Sleeps 6

“Excellent Villa except for the sofa bed” Absolutely gorgeous place to stay. The Villa was very spacious and comfortable for my family of 6. We went to Sarasota for a graduation and were able to have my family over for a visit from Miami without a prob

$171

1 / 17

Gorgeous Direct gulf Front 2 Bedroom Condo on Siesta Keys... JUST REMODELLED

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$155

1 / 31

crescent arms 105n 1st floor 40 yards from the beach

Siesta Key condo

2 bedrooms / 2 bathrooms / Sleeps 6

$178

1 / 21

6 South

Siesta Key apartment

1 bedroom / 2 bathrooms / Sleeps 4

“Peaceful,clean,furnished to perfection and a loving calm for my” Our enjoyment began with the inital phone conversation with Scott. I shared with him what my wife and I were looking for ---to enjoy our 45th wedding anniversary. What a gift!

$222

1 / 16

2 Bedroom 2 Bath Home in Siesta Village

Siesta Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$275

1 / 9

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.

$225

1 / 21

Siesta Key Beach House

Siesta Key house

3 bedrooms / 3 bathrooms / Sleeps 8

“Paradise!!” I have stayed in Siesta Key well over 25 times, and this house is truly unique! It's spacious, well-appointed, clean, and has a lot of extras (baby walker, baby gate, tons of beach toys and equipment). We just got back and I miss it alread

$237

1 / 16

NEW EVERYTHING Luxury 1 Bedroom King Villa 3 Pool Walk to beach JAN SPECIALS

Siesta Key apartment

1 bedroom / 1 bathroom / Sleeps 3

$129

1 / 13

Firethorn 212

Siesta Key apartment

2 bedrooms / 1 bathroom / Sleeps 4

$207

1 / 26

Doveplum 121

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$236

1 / 14

Chinaberry 912

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$147

1 / 22

Only 150 yards to Crescent Beach and heated pool!

Siesta Key villa

2 bedrooms / 1 bathroom / Sleeps 4

“Amazing Rental” This rental was roomier than expected! Everything was perfect! The pool and beach is so close, also there is some local restaurants and shops so close by! Couldn't have asked for better!

$119

1 / 58

14 North

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

“Great getaway!” Our family enjoyed a long weekend around Labor Day weekend at Island House. We have stayed at Island House before and always have a good time. Fabulous beach, helpful staff, relaxing place to be. This was our first time staying in 14

$222

1 / 19

Old Man and the Sea Inn #2 - 8 steps to the sand of Siestas best beach!

Siesta Key house

1 bedroom / 1 bathroom / Sleeps 4

$115

1 / 23

Chinaberry 423

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$220

1 / 36

Best Deals on Siesta Key

Siesta Key apartment

1 bedroom / 1 bathroom / Sleeps 4

“Great location.” Away from the crowds, but close to everything. 2 minute walk to the beach and access to a pool!! Friendly owner next door. Perfect for 2 people.

$90

1 / 30

3 South

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

“beautiful retreat, loving this place!” the place is awesome! very good size rooms! love to wake up in the morning in the masters bedroom w/ curtains open because the beautiful sight welcomes you! family eating bfast at the balcony w/ the view of the b

$222

1 / 16

Doveplum 120

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$255

1 / 37

Chinaberry 952

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$147

1 / 19

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

Siesta Key villa

2 bedrooms / 2 bathrooms / Sleeps 6

$180

1 / 26

Villa 17

Siesta Key villa

2 bedrooms / 2 bathrooms / Sleeps 4

“Perfect Getaway from the Cold!” We had the most perfect getaway from the blistery cold of Chicago! The villa was in excellent condition, especially clean and cozy. The grounds are given great care. The staff was so friendly, we truly felt welcome and

$171

1 / 20

Villa 9

Siesta Key villa

2 bedrooms / 2 bathrooms / Sleeps 6

“Our vacation at Siesta Key was as always relaxing and enjoyable.” Villa 9 was newly redecorated; therefore, it was a pleasure to spend 10 days in a clean, updated, and comfortable villa. The comfort of Villa 9 was worth a little bit of a walk to the

$171

1 / 18

SIESTA KEY! #1 Beach! Tranquil Gulf-side 2 Bed/2 Bath in Jamaica Royale #104

Siesta Key condo

2 bedrooms / 2 bathrooms / Sleeps 6

$160

1 / 20
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