Vacation Rentals & Beach Rentals in Siesta Key

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337 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. 1 hour 1 minutes

Match: Boat available Towels provided

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Price per night from

$267

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Boat available Towels provided

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Price per night from

$206

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Towels provided

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Price per night from

$345

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.

Match: Boat available Towels provided

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Price per night from

$509

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!

Match: Boat available Towels provided

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Price per night from

$273

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Boat available Towels provided

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Price per night from

$490

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Boat available Towels provided

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Price per night from

$490

Split Leaf at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Boat available Towels provided

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Price per night from

$490

Coconut at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Boat available Towels provided

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Price per night from

$490

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Harbor Towers

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$138

Tiny House Siesta - Yellow Lifeguard Stand Tiny House

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Towels provided

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Price per night from

$423

Beautiful, Affordable Close to famous Siesta Beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“It was wonderful!” Everything about the trip and condo was great! Mike met us to give us the keys and we called him for suggestions about restaurants, etc. and he was very helpful. The condo was very clean and had everything we needed. It was also great that we were able to use the beach chairs and umbrella. I am already trying to figure out when we can go again.

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$163

Tiny House Siesta - Sand Dollar – A private master loft and open living space

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Towels provided

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Price per night from

$448

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$490

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$490

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$490

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 23 minutes

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$390

Siesta Key beach & sunsets - 2018 Spring & Summer openings!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Boat available, Towels provided

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Price per night from

$131

Beachfront Getaway in Siesta Key

Siesta Key townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Very comfortable, nice amenities and well run.” Loved the beach and the nearby restaurants. The free trolly ride was easy to use and a great way to go into the village.

1 of 2 match: Boat available, Towels provided

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Price per night from

$224

“gracious and spacious” Lovely home and great location to walk throughout Siesta Key Village and the beautiful sands of the beach!! We were able to have everyone together for a great vacation.

1 of 2 match: Boat available, Towels provided

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Price per night from

$148

Luxury Village Townhouse w/ Gulf and Beach Views

Siesta Key townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“A wonderful home in an equally wonderful location.” The home provides a truly enjoyable family situation. The quality of the furnishings is very nice, the living space is very well maintained and clean and my interaction with the owner was always timely and courteous. My wife and I shared the home with our 14 year old granddaughter during our stay and the quiet enjoyment of the pool and the easy 1-2 minute walk to the Gulf of Mexico and the 5 minute walk to the heart of Siesta Key Village made the location hard to beat. Except for our day trips no car was needed. This is our second stay in the home and we will look to reserving it for our next visit. There were absolutely no disappointments only wonderful experiences.

1 of 2 match: Boat available, Towels provided

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Price per night from

$659

Family Tides - High Tides: By Beachside Management

Siesta Key apartment

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$549

120 Steps to the Beach with beach gear included!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$424

Siesta Surf Cottage #1

Siesta Key log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$140

Siesta Beach House - 204

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$115

Siesta Surf Cottage #3

Siesta Key log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$153

Siesta Beach House - 203 / Sunny Daze

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$115

Siesta Beach House - 202

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$115

Siesta Beach House - 310 / Come n' Beach It

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$115

Beach Road - Bari

Siesta Key studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$79

Beach Road - Capri

Siesta Key studio

  • Studio
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$91

Vista Hermosa - 302C

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$172

Sea Club II

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$166

Beautiful Crescent Beach on Siesta Key One of the

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$301

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$410

Beautiful Townhouse in Prime Location with Private Beach Access!

Siesta Key townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$238

#1 EXCLUSIVE Siesta Key Beach House /3 payments

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$259

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Towels provided

1 of 2 filters match

Price per night from

$230

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