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Siesta Key Rentals

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Siesta Key Rentals

545 beach 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

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

1 / 50

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

1 / 17

Palm Oasis - Relax in Comfort -

Siesta Key house

4 bedrooms / 3 bathrooms / Sleeps 10

$358

1 / 35

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

Siesta Key house

4 bedrooms / 4 bathrooms / Sleeps 8

$429

1 / 13

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

Siesta Key apartment

2 bedrooms / 1 bathroom / Sleeps 6

$106

1 / 30

Firethorn 323

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$218

1 / 20

Chinaberry 455

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$220

1 / 16

16 North

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

“Awesome place!” We have been to Island House 4 times now! Every stay has been nothing but perfect! It is truly an island paradise! We will be back!

$222

1 / 15

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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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

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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

1 / 18

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$130

1 / 30

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$114

1 / 30

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

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$152

1 / 31

Villa 8

Siesta Key villa

2 bedrooms / 2 bathrooms / Sleeps 6

$163

1 / 16

13 North

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

“FABULOUS” The property was very well maintained, the staff very helpful, the house beautiful and very clean and the beach was fantastic. Loved the pool for adults and the watersports area and beach snack bar were well maintained and very nice. We spe

$222

1 / 22

Beachfront - 1-Bedroom Condo at Fisherman's Cove - Free Boat Docks -Ground level

Siesta Key apartment

1 bedroom / 1 bathroom / Sleeps 4

“Great location right on the beach.” Nicely decorated condo. We walked out on the beach with our coffee in the morning and watched the sunsets at happy hour! We were located near destinations but liked the seclusion of this condo.

$119

1 / 41

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

$233

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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

Firethorn 512

Siesta Key apartment

2 bedrooms / 1 bathroom / Sleeps 4

$125

1 / 13

Buttonwood 910

Siesta Key apartment

3 bedrooms / 2 bathrooms / Sleeps 6

$178

1 / 33

2 Bedroom 2 Bath Home in Siesta Village

Siesta Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$275

1 / 9

17 South

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

“Island House Rocks” Great Labor Day Weekend thanks to Island House and Siesta Key Beach. Even the occasional sharks that passed by were extremely cordial and work horse employee Juan (the "no chairs past the sign" man) was his usual bubbly and helpful

$222

1 / 18

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

Siesta Key condo

2 bedrooms / 2 bathrooms / Sleeps 6

$175

1 / 21

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 514

Siesta Key apartment

2 bedrooms / 1 bathroom / Sleeps 4

$120

1 / 30

Villa 39

Siesta Key villa

2 bedrooms / 2 bathrooms / Sleeps 6

$171

1 / 17

Chinaberry 443

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$220

1 / 15

Firethorn 510

Siesta Key apartment

2 bedrooms / 1 bathroom / Sleeps 4

$125

1 / 19

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

1 / 18

Firethorn 513

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$125

1 / 14

Villa 34

Siesta Key villa

2 bedrooms / 2 bathrooms / Sleeps 4

“A Great Get-A-Way” Our summer vacation this year was wonderful. Although, my sister and her husband did not have the opportunity to join us, my husband and I had a terrific time. Relaxing by the pool, lying on the beach, seeing beautiful sunsets, and

$171

1 / 15

Beachy Chic Condo in Siesta Key - Waterfront - Free wifi - Sleeps 4 !

Siesta Key apartment

1 bedroom / 1 bathroom / Sleeps 4

“Wonderful rental! Location ideal.” This is a wonderful rental. I recommend this rental to anyone who wants a comfortable condo for their stay at the beach. It has one bedroom, a family room and a kitchen along with a flat screen TV and wireless intern

$120

1 / 31

12 South

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$222

1 / 15

Doveplum 112

Siesta Key apartment

4 bedrooms / 3 bathrooms / Sleeps 8

$385

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