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Vacation Rentals & Beach Rentals in Siesta Key

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50 beach rentals

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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Price per night from

$196

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$125

Beach Place Cottages - Seahorse Cottage - Peak of the Gulf - Beach Access #11

Siesta Key cottage

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$206

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$304

Siesta Key private beach access

Siesta Key villa

3 bedrooms / 3 bathrooms / sleeps 8

“Siesta Key Townhouse” This was a wonderful place to stay! The house was very clean and spacious and had everything we needed for a week at the beach.

Responds fast! avg. 3 hours 2 minutes

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$442

Sandy Toes Town Home

Siesta Key townhouse

3 bedrooms / 3 bathrooms / sleeps 6

“Time in Paradise” We recently had the luck to spend two months in paradise. This condo was comfortably appointed, well stock to meet all our needs, and most importantly in the perfect location. The beach was a short walk to the left and stores and restaurants were just a short walk to the right. We had a great time and enjoyed everything Sarasota, Siesta Key, and this Sandy Toes Condo had to offer. Thanks Mark!

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Price per night from

$277

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Price per night from

$206

Great rentals within 20 miles that match your search

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$385

LAKEFRONT,POOL,WALK TO BEACH, FREE KAYAKS,BICYCLES

Nokomis house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$127

Legacy Trail Retreat

Nokomis house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 18 minutes

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Price per night from

$174

BAY VIEW. SUNSETS. CLOSE TO ANNA MARIA ISLAND AND IMG ACADEMY

Bradenton house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$291

Dream Lover Boat & Breakfast on Anna Maria Island

Bradenton Beach yacht

2 bedrooms / 2 bathrooms / sleeps 4

“Celebrate Birthdays & 24th Anniversary” We had a wonderful time on the Dream Lover this weekend. It was a special way to celebrate our birthdays and 24th Wedding Anniversary. We spent early mornings up on deck. The breakfasts were amazing! Love the area - so easy to walk to many restaurants, stores, and the beach. Kay and Jonathan are a wonderful couple wit such a positive and healthy outlook on life. They are a joy to spend time with. Oh and Skipper too!!! I was a wonderful weekend. Sue & Jim Hughes

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Price per night from

$307

Siesta Beach Cottage

Sarasota apartment

2 bedrooms / 1 bathroom / sleeps 6

“Beautiful place!” Enjoyed our stay in Sarasota on this property! We were not there much but when we were it felt like home. Very clean inside and out. The owner Kimberly showed us were everything was when we got there. Had a nice pool but too cold out to use it. Very quiet neighborhood. We would rent this property again!

Responds fast! avg. 3 hours 8 minutes

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Price per night from

$216

Sandy Pointe #205

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$127

TORTUGA BEACH CLUB, SIESTA KEY

Sarasota apartment

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$248

Beautiful Braden River Waterfront Retreat!

Bradenton house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 32 minutes

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Price per night from

$150

Anna Maria Island Beach Waves

Cortez condo

1 bedroom / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$162

Anna Maria Island Beach View 207

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$126

Anna Maria Island Beach Sands 203

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$142

Anna Maria Island Beach Palms 5B

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$139

Anna Maria Island Beach Paradise 5

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$178

Anna Maria Island Beach Palace

Bradenton Beach house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$463

Anna Maria Island Beach Palms 2A

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$130

Anna Maria Island Sunshine Kiss Villa

Holmes Beach condo

1 bedroom / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$123

Anna Maria Island Beach Palms 6B

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$131

Anna Maria Island Beach View 209

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$133

Anna Maria Island Bridge Port Beach Resort

Bradenton Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$122

Anna Maria Island Beach Palms 7A

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$130

Anna Maria Island Bay Watch Bungalow

Bradenton Beach condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$139

Anna Maria Island Beach Sands 101

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$184

Anna Maria Island Beach Paradise 10

Holmes Beach studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$208

Anna Maria Island Beach Paradise 6

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$178

Anna Maria Island Beach Palms 2B

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$153

Anna Maria Island Beach Haven

Cortez house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$463

Anna Maria Island Beach Breeze

Bradenton Beach apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$155

Anna Maria Island Beach Sands 201

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$184

Anna Maria Island Beach Bay Breeze

Bradenton Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$122

Anna Maria Island Beach Palms 8B

Cortez condo

1 bedroom / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 26 minutes

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Price per night from

$127

Viewing 38 of 50
rentals in Siesta Key

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