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Siesta Key Rentals

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Siesta Key Rentals

544 beach rentals

2018 Reduced winter rates! Waterfront Seista Key home with dock and private pool

Siesta Key house

4 bedrooms / 4 bathrooms / Sleeps 8

$429

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

Siesta Key apartment

1 bedroom / 1 bathroom / Sleeps 3

$129

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Siesta Key 3BR/2BA- Buttonwood 940

Siesta Key apartment

3 bedrooms / 2 bathrooms / Sleeps 6

$179

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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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Water Views, Private Beach Access, Wifi Incl. Renovated Condo With Amenities

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$114

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

Siesta Key condo

2 bedrooms / 2 bathrooms / Sleeps 6

$175

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Crescent Beach Gulf Side 2BR/2BA- Chinaberry 414

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$220

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Firethorn 313

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$219

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Firethorn 821

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$125

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Doveplum 120

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$255

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Doveplum 624

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$147

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Firethorn 722

Siesta Key apartment

2 bedrooms / 1 bathroom / Sleeps 6

$125

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Buttonwood 467

Siesta Key apartment

3 bedrooms / 2 bathrooms / Sleeps 6

$236

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6 North

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

“Fantastic” The view, sunset, beach, quietness, comfort, ... There are many words that would describe Island House...gorgeous and fantastic are appropriate. The staff, especially Scott, the office staff, the grounds people, and the cleaning staff...are

$222

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5 South

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

“Wonderful!” We enjoyed our stay at Island House and unit 5South very much. It was extremely clean, quiet and relaxing. The location to the beach couldn't be better without being right in the ocean! I would have given 5 stars but the shower in the mas

$222

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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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Villa 8

Siesta Key villa

2 bedrooms / 2 bathrooms / Sleeps 6

$163

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Chinaberry 912

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$147

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3 North

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

“Relax and chill out” We have stayed at this apartment twice once in 2005 and 2008 after Island house was recommended to us by friends, the first time we stayed we all fell in love with Siesta keys and island house, and when we visited again we asked t

$222

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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

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15 North

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

“Great Siesta Key stay!” Just returned from 4 short days on Siesta Key at Island House - 15N...and am missing everything about it! While this development was NOT built yesterday, we found it to be in great shape - nicely kept landscaping, beautiful wa

$222

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Firethorn 332

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$219

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$152

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Villa 5

Siesta Key villa

2 bedrooms / 2 bathrooms / Sleeps 6

“Great location and lovely accommodations!” This was our second year to vacation here and we plan to return next year! It is so close to the beautiful beach. Our experiences have been very relaxing and worth repeating.

$171

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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

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Doveplum 623

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$147

1 / 46

Firethorn 610

Siesta Key apartment

2 bedrooms / 1 bathroom / Sleeps 6

$125

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Chinaberry 942

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$147

1 / 38

Siesta Key Completely Renovated 3BR/2BA- Buttonwood 950

Siesta Key apartment

3 bedrooms / 2 bathrooms / Sleeps 6

$179

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4 South

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

“A wonderful family vacation!” We loved our stay at the Island House! The staff and property were excellent! The rental unit was perfect! the view was amazing and the pool/club house made for an ideal family trip. My children and I would love to go

$222

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Crescent Beach Gulf Side 3BR/2BA- Buttonwood 417

Siesta Key apartment

3 bedrooms / 2 bathrooms / Sleeps 6

$236

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Firethorn 514

Siesta Key apartment

2 bedrooms / 1 bathroom / Sleeps 4

$121

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Firethorn 323

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$219

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Chinaberry 455

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$220

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Private beach with lounges and umbrellas!

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

“Fabulous apartment. Fabulous siesta key” We stayed for 2 weeks in July august and had a fabulous time. The apartment is very spacious. It is much bigger than photos make it look. It is very well equipped and lovely. The bed is amazingly comfortable an

$125

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Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Ground Floor

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

“Lovely condo on the beach, beautiful sunsets, quiet and relaxing” We recently had another nice vacation in this first floor condo, right on the gulf. Attractive décor, well equipped kitchen, large walk-in closet, washer and dryer. Convenient parking s

$150

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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

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Gulf Front 1 Bedroom Condominium on Siesta Key

Siesta Key villa

1 bedroom / 1 bathroom / Sleeps 4

$150

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