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Siesta Key Rentals

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Siesta Key Rentals

545 beach rentals

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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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

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$110

1 / 30

Siesta Key - 2BR - Beachfront Condo on Crescent Beach - Heated Pool - Tennis Ct

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$159

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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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Beachfront - 1-Bedroom Condo at Fisherman's Cove - Free Boat Docks - 3rd Floor

Siesta Key apartment

1 bedroom / 1 bathroom / Sleeps 4

$119

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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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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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Water, sun, fun siesta key2bedroom condo 2 bath

Siesta Key condo

2 bedrooms / 2 bathrooms / Sleeps 4

$143

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

Siesta Key condo

2 bedrooms / 2 bathrooms / Sleeps 6

$175

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SEA SHELL - Siesta Key Beach View Vacation Condo - 2 BR - on Crescent Beach

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

“Wonderful location!” We enjoyed a great week at this condo. The location was perfect. Close enough to walk for groceries or dining but not too busy and chaotic like it is near the north village area. The condo was comfortable,clean and well equipped.

$148

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Palm Bay Club - 100 Yards From The Beach

Siesta Key condo

2 bedrooms / 2 bathrooms / Sleeps 8

$210

1 / 29

Palm Oasis - Relax in Comfort -

Siesta Key house

4 bedrooms / 3 bathrooms / Sleeps 10

$358

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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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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

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Siesta Key 2 BR, 2 1/2 Bath - *Across From Beach - Pool-view* - Newly Renovated

Siesta Key apartment

2 bedrooms / 3 bathrooms / Sleeps 8

$179

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11 South

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

“Wonderful View of the Gulf” We had a wonderful stay at Island House Beach Resort...Unit 11 S. We were arriving after the office closed so the keys were left in the unit with the lights on which made checking in very easy. The manager was very respon

$222

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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

$150

1 / 32

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

1 / 30

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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Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 5

$96

1 / 32

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

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

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

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BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - RENOVATED

Siesta Key apartment

3 bedrooms / 2 bathrooms / Sleeps 8

“Trip to paradise” Renting unit was very easy. Unit was the best layout was great. Amenities within we're well thought, out and for us anything we wanted was there including beach chairs. View of ocean was breath taking along with sunsets. I will com

$182

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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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Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key

Siesta Key apartment

3 bedrooms / 2 bathrooms / Sleeps 8

“Great location!” The unit was just as described and pictures matched. The view of the ocean and bay were gorgeous. The kitchen was well equipped and there were lots of toys and chairs for the beach.

$182

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Firethorn 513

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 4

$125

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SEA SHELL - Siesta Key Beachfront Vacation Condo complex on Crescent Beach - 2BR

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

“Great family vacation” We have stayed in the same unit for over 15 years. it is located where our men have boat slips we also have a lovely pool and beach front. The unit is supplied with all you need for furnishings and supplies. The people are very

$148

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Crescent Beach - 2 Bedroom - Beachfront Condo Complex - Heated Pool

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

“amazing location. amazing condo” Directly in crescent beach and walking distance from south village the location was fabulous. Condo was way more than we expected, really nice. Sunnyside Properties has thought of everything.

$139

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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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Tiny House Siesta - Yellow Lifeguard Stand Tiny House

Siesta Key hotel apartment

2 bedrooms / 1 bathroom / Sleeps 4

$162

1 / 32

Crescent Beach, Siesta Key, 2br/2bath Garden Unit, free WIFI, Netflix

Siesta Key apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$156

1 / 27

2 Bedroom 2 Bath Home in Siesta Village

Siesta Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$275

1 / 9

Beachfront Condo Siesta Key: Fall Specials!!

Siesta Key condo

2 bedrooms / 2 bathrooms / Sleeps 6

“Very enjoyable second stay” This was our second stay in the condo, our first in the summer. The condo was clean and comfortable ,and the location across the street from the public beach couldn't be beat. With an easy 10 - 15 min. walk to the town cent

$159

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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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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

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