Vacation Rentals & Beach Rentals in Siesta Key

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332 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

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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

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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

$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.

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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!

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Price per night from

$273

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$490

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$490

Split Leaf at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$490

Coconut at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$490

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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, Clothes dryer

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Price per night from

$163

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Clothes dryer

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Price per night from

$490

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Clothes dryer

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Price per night from

$490

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Clothes dryer

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Price per night from

$490

Beach Road - Bari

Siesta Key studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 2 match: Boat available, Clothes dryer

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Price per night from

$79

Beach Road - Capri

Siesta Key studio

  • Studio
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Clothes dryer

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Price per night from

$91

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, Clothes dryer

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Price per night from

$659

Beautiful Crescent Beach on Siesta Key One of the

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Boat available, Clothes dryer

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Price per night from

$301

Quiet and Comfortable Condo Near Turtle Beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Siesta sweet spot” Great value for location. Nice pool, visits with the manitees. Close to everything. This time of year ocean water was amazing

1 of 2 match: Boat available, Clothes dryer

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Price per night from

$201

Lovely Siesta Key 3BR 2.5BA Condo, Island Paradise

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Clothes dryer

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Price per night from

$493

Beautiful Townhouse in Prime Location with Private Beach Access!

Siesta Key townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Clothes dryer

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Price per night from

$238

Costal Surfside 298: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Clothes dryer

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Price per night from

$457

Banana Cabana: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Clothes dryer

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Price per night from

$240

Beach House Residence - Penthouse; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Boat available, Clothes dryer

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Price per night from

$434

Bay Oaks - E35

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Boat available, Clothes dryer

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Price per night from

$171

Siesta Avenue

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Clothes dryer

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Price per night from

$195

Happy Blue Coconuts - North

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Boat available, Clothes dryer

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Price per night from

$400

Siesta Beach House - 311 / Beach Cove

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Boat available, Clothes dryer

1 of 2 filters match

Price per night from

$115

A Shell House Casa

Siesta Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Clothes dryer

1 of 2 filters match

Price per night from

$176

Plymouth Harbor

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Clothes dryer

1 of 2 filters match

Price per night from

$269

Siesta Escape - B

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Boat available, Clothes dryer

1 of 2 filters match

Price per night from

$338

Midnight Cove II - Doveplum

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Clothes dryer

1 of 2 filters match

Price per night from

$144

Alvarado

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Boat available, Clothes dryer

1 of 2 filters match

Price per night from

$127

Bayside Pointe

Siesta Key townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Boat available, Clothes dryer

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Price per night from

$161

Holiday House 1

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Clothes dryer

1 of 2 filters match

Price per night from

$91

Bay Oaks - E82

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Boat available, Clothes dryer

1 of 2 filters match

Price per night from

$115

Casa Covella

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Clothes dryer

1 of 2 filters match

Price per night from

$219

Cortez Avenue

Siesta Key townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Clothes dryer

1 of 2 filters match

Price per night from

$204

Siesta Escape - A

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Boat available, Clothes dryer

1 of 2 filters match

Price per night from

$313

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