Vacation Rentals & Beach Rentals in Siesta Key

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323 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: Housekeeping Included Swimming pool

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Price per night from

$266

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Price per night from

$333

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$410

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$109

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$344

Amazing Beachfront Condo, Siesta Key,

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$344

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Price per night from

$458

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN CONDO!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Housekeeping Included Swimming pool

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Price per night from

$272

Crystal Sands - 206 Tower: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Housekeeping Included Swimming pool

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Price per night from

$263

Ten35 Seaside - Direct Gulf View: Residence 405

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Housekeeping Included Swimming pool

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Price per night from

$859

Ten35 Seaside - Direct Gulf View: Residence 303

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Housekeeping Included Swimming pool

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Price per night from

$859

Ten35 Seaside - Direct Gulf View: Residence 403

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Housekeeping Included Swimming pool

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Price per night from

$859

Ten35 Seaside - Direct Gulf View: Residence 301

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Housekeeping Included Swimming pool

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Price per night from

$859

Ten35 Seaside - North Water View: Residence 506

Siesta Key condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$779

Ten35 Seaside - Direct Gulf View: Residence 307

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$859

Ten35 Seaside - North Water View: Residence 606

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$779

Ten35 Seaside - North Water View: Residence 310

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$630

Ten35 Seaside - Island View: Residence 308

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Housekeeping Included Swimming pool

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Price per night from

$550

Ten35 Seaside - South Water View: Residence 602

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$687

Ten35 Seaside - North Water View: Residence 410

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$630

Ten35 Seaside - South Water View: Residence 302

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$607

Ten35 Seaside - South Water View: Residence 502

Siesta Key condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$756

Ten35 Seaside - Island View: Residence 408

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Match: Housekeeping Included Swimming pool

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Price per night from

$550

Ten35 Seaside - Island View: Residence 604

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$561

Ten35 Seaside - Island View: Residence 406

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$561

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“Great stay in Sarasota” My husband and our two daughters spent a wonderful four days in Sarasota. The townhome we stayed in was beautiful and had all the amenities we needed. We spent every day at the beach and relaxed at the townhome in the evenings. We would definitely stay here again and have recommended this place to our family and friends. Thanks Louie!

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Housekeeping Included, Swimming pool

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Price per night from

$435

4 minute flip flop walk to the beach! Starfish 2/2

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$339

Siesta Key Gulf View Condo

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 33 minutes

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Price per night from

$448

Luxury Waterfront Views/Pool/1400sf/2 min to Beach

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Housekeeping Included, Swimming pool

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Price per night from

$340

Siesta Key vaca rental

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$230

Frangi Pani at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$490

Best of both worlds! Fish in bay or go to beach!

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Modern place in an awesome location” My family really enjoyed our time at this place. It was very clean, a convenient end unit, and close to the beautiful beach. Having the Intracoastal and pool was great, too. Being fully stocked and 2 TVs was a welcome surprise. Thanks for a great stay!

1 of 2 match: Housekeeping Included, Swimming pool

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Price per night from

$229

Ten35 Seaside - Direct Gulf View: Residence 601

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$928

Siesta Key/Derby Bay

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect!” Our family really enjoyed staying here! The villa was very well maintained and cleaned. It was stocked with everything you would need. The owner was very responsive to any concerns. We had a super nice neighbor and my boys loved fishing off the dock. I would recommend renting a golf cart to go to the beach if you have children (with toys etc) or elderly people with walking concerns. It is quite a walk to get to the beach (because you also have to walk down to the cross walk then across the street). The beach in front of the Aloha Kai property is very wide (great because it was never crowded like in front of other resorts) but it was an even farther walk to the water. We have always stayed beach front but needed more rooms than were available in my booking time frame this year. This property has changed the way I will book on siesta in the future. My boys LOVED fishing everyday off the dock. They caught lots of cool fish right off the back. The street that this villa is on was very quiet for our stay. Everyone was very kind & the property is very beautiful! We hope to come back very soon! It was a wonderful experience.

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Price per night from

$287

Beach Vacation rental

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$247

Beach house for rent in siesta key beach.

Siesta Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Responds fast! avg. 1 hour 59 minutes

1 of 2 match: Housekeeping Included, Swimming pool

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Price per night from

$1,004

Condo wOcean view on Siesta

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 33 minutes

1 of 2 match: Housekeeping Included, Swimming pool

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Price per night from

$402

Beautiful house for rent at siesta key beach with pool, theater and game room

Siesta Key house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 15

Responds fast! avg. 1 hour 59 minutes

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Price per night from

$2,854

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rentals in Siesta Key

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