Vacation Rentals & Beach Rentals in Siesta Key

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310 beach rentals

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“It was very cozy and comfortable apartment!” We loved to spend our vacation at this place. Really close to the beach, to different restaurants, and all kind of stores.

Match: Table tennis Towels provided

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Price per night from

$115

Siesta Key Beach : 2 Bedroom, 3 Beds, 3 Bathroom Duplex & Heated Pool

Siesta Key apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Table tennis Towels provided

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Price per night from

$182

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Table tennis Towels provided

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Price per night from

$109

“Anniversary Trip” Had a wonderful time at LA Siesta Condominiums for our anniversary vacation. Beautifully furnished and do close to the best beach in the USA

Match: Table tennis Towels provided

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Price per night from

$245

Gulf and Bay Club 3bdrm “E” Luxury END CORNER Unit - RIGHT ON BEACH

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Table tennis Towels provided

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Price per night from

$901

Beachfront Condo Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!

Match: Table tennis Towels provided

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Price per night from

$452

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Table tennis Towels provided

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Price per night from

$229

Discover the perfect beachfront getaway with a private pool & hot tub.

Siesta Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Table tennis Towels provided

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Price per night from

$852

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Table tennis Towels provided

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Price per night from

$489

Super Cute Cottage--Private--Walk/Bike to Beach

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Table tennis Towels provided

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Price per night from

$258

Off the Hook: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 40 minutes

Match: Table tennis Towels provided

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Price per night from

$514

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Table tennis Towels provided

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Price per night from

$489

Las Palmas; by Beachside Management

Siesta Key house

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

Responds fast! avg. 1 hour 40 minutes

Match: Table tennis Towels provided

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Price per night from

$1,200

Split Leaf at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Table tennis Towels provided

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Price per night from

$489

Coconut at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Table tennis Towels provided

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Price per night from

$489

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Table tennis Towels provided

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Price per night from

$489

*** SUPER SPECIAL RATES at Harbor Towers ***

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

Match: Table tennis Towels provided

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Price per night from

$114

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Table tennis Towels provided

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Price per night from

$489

Beach Walk: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 40 minutes

Match: Table tennis Towels provided

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Price per night from

$514

A Somewhere is Here - Changes in Latitude: By Beachside Management

Siesta Key apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 40 minutes

Match: Table tennis Towels provided

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Price per night from

$457

Indulge in a spacious 4-bedroom rental with private pool and beach access!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Table tennis Towels provided

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Price per night from

$972

A Somewhere Is Here - Changes in Attitude: By Beachside Management

Siesta Key apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 40 minutes

Match: Table tennis Towels provided

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Price per night from

$411

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Table tennis Towels provided

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Price per night from

$489

These homes match some but not all of your filters. Clear all filters

Harbor Towers

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Towels provided

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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: Table tennis, Towels provided

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Price per night from

$421

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: Table tennis, Towels provided

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Price per night from

$223

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: Table tennis, Towels provided

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Price per night from

$446

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: Table tennis, Towels provided

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Price per night from

$163

120 Steps to the Beach with beach gear included!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Towels provided

1 of 2 filters match

Price per night from

$423

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: Table tennis, Towels provided

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Price per night from

$389

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Table tennis, Towels provided

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Price per night from

$131

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: Table tennis, Towels provided

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Price per night from

$658

Family Tides - High Tides: By Beachside Management

Siesta Key apartment

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Table tennis, Towels provided

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Price per night from

$548

“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: Table tennis, Towels provided

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Price per night from

$148

Siesta Beach House - 203 / Sunny Daze

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Towels provided

1 of 2 filters match

Price per night from

$115

Beach Road - Capri

Siesta Key studio

  • Studio
  • 1 bathroom
  • sleeps 4

1 of 2 match: Table tennis, Towels provided

1 of 2 filters match

Price per night from

$91

Beach Road - Bari

Siesta Key studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 2 match: Table tennis, Towels provided

1 of 2 filters match

Price per night from

$79

Vista Hermosa - 302C

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Towels provided

1 of 2 filters match

Price per night from

$172

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