Vacation Rentals & Beach Rentals in Siesta Key

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1,076 beach rentals

Dream View. Really beautiful home, every extra imaginable, fantastic pool view.

Rotonda West villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Shared indoor pool Toaster

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Price per night from

$376

Paradise by lakeside & views over golf course, fantastic 2 master suites

Rotonda West villa

  • 4 bedrooms
  • 8 bathrooms
  • sleeps 8

Match: Shared indoor pool Toaster

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Price per night from

$342

Haven Hideaway lives up to its name. Perfect holiday villa

Rotonda West villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Shared indoor pool Toaster

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Price per night from

$261

Stunning BRAND NEW 3 bed home, fabulous pool overlooking river,

Rotonda West villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared indoor pool Toaster

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Price per night from

$319

Really stunning home, perfect position, south facing overlooking the river

Cape Haze villa

  • 4 bedrooms
  • 8 bathrooms
  • sleeps 8

Match: Shared indoor pool Toaster

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Price per night from

$169

Superb Home Perfect Place, true description of this wonderful villa. Your

Rotonda West villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Shared indoor pool Toaster

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Price per night from

$261

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LaPlaya 205D-Spectacular sunsets from your private Gulf-front lanai or sundeck.

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Toaster, Shared indoor pool

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Price per night from

$414

LaPlaya 102B-Directly on the beach with the warm Gulf waters waiting!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Toaster, Shared indoor pool

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Price per night from

$339

LaPlaya 107A-Soak up the sun or float in the warm Gulf waters.

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Toaster, Shared indoor pool

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Price per night from

$311

1 of 2 match: Toaster, Shared indoor pool

1 of 2 filters match

Price per night from

$414

1 of 2 match: Toaster, Shared indoor pool

1 of 2 filters match

Price per night from

$376

LaPlaya 106A-Beach front! Steps to the white sand and turquoise Gulf of Mexico.

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Toaster, Shared indoor pool

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Price per night from

$376

LaPlaya 204D-Beach-lovers paradise! 200 feet of private beach

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Toaster, Shared indoor pool

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Price per night from

$414

LaPlaya 206C-Gorgeous vistas of the Gulf

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Toaster, Shared indoor pool

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Price per night from

$414

1 of 2 match: Toaster, Shared indoor pool

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Price per night from

$220

LaPlaya 104A- Gulf front! Walk right from your lanai onto the private beach.

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Toaster, Shared indoor pool

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Price per night from

$311

1 of 2 match: Toaster, Shared indoor pool

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Price per night from

$414

LaPlaya 101E-Relax on your private lanai under the palms!

Longboat Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Toaster, Shared indoor pool

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Price per night from

$275

Monthly Rental, 2 bed, 2 bath, Ocean view.

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Toaster, Shared indoor pool

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Price per night from

$115

A view of Gulf of Mexico, plus access to all the resort amenities! A3214C

Don Pedro Island villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Shared indoor pool, Toaster

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Price per night from

$454

Tiny House - Blue Lifeguard Stand

Gulf Gate Branch house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Toaster

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Price per night from

$422

Tiny House - Flamingo

Gulf Gate Branch house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared indoor pool, Toaster

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Price per night from

$399

Tiny House - Green Lifeguard Stand

Gulf Gate Branch house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Shared indoor pool, Toaster

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Price per night from

$464

Tiny House - Seashell

Gulf Gate Branch house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Shared indoor pool, Toaster

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Price per night from

$314

Tiny House - Margarita

Gulf Gate Branch house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared indoor pool, Toaster

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Price per night from

$470

Tiny House - The Siesta

Gulf Gate Branch house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Shared indoor pool, Toaster

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Price per night from

$374

Piece of Paradise

Sarasota condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 minutes

1 of 2 match: Shared indoor pool, Toaster

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Price per night from

$95

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: Shared indoor pool, Toaster

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Price per night from

$163

SunWay Suites Unit 2 Plover

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Toaster

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Price per night from

$23

SunWay Suites Unit 4 Pelican

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Toaster

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Price per night from

$138

Casey Key 1-Bed Villa #2

Nokomis villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared indoor pool, Toaster

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Price per night from

$172

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 46 minutes

1 of 2 match: Shared indoor pool, Toaster

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Price per night from

$194

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: Shared indoor pool, Toaster

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Price per night from

$447

Private modern 3BR home, salt water pool

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Toaster

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Price per night from

$344

Beach Villa Paradise

Englewood villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Toaster

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Price per night from

$172

Great location, quiet, peaceful, and comfortable

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared indoor pool, Toaster

1 of 2 filters match

Price per night from

$46

Anna Maria Island Beach Haven

Cortez house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Shared indoor pool, Toaster

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Price per night from

$1,500

New York Avenue Rancher

Gulf Gate Estates house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared indoor pool, Toaster

1 of 2 filters match

Price per night from

$445

Viewing 38 of 1,076
rentals in Siesta Key

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