Vacation Rentals & Beach Rentals in Siesta Key

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414 beach rentals

Crescent Beach resort, Heated Pool, Jacuzzi, Tennis, Barbeques

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$316

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$1,001

A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

“Your best choice for location!” We stayed for 10 lovely days in this home and I have to say It was an even better location than I expected. Everything you could want to do is in walking distance or you can walk to the village (maybe a 3 minute walk)and hop in a free taxi . The house is well appointed and beds are very comfortable. We traveled with a 10 yr.old, 11yr. old , and 15 yr. old my 15 yr. old niece slept in the trundle bed and commented on how comfortable the bed was. In the kitchen you will find a drawer full of menus for the many nearby restaurants and information for water activities. I highly recommend parasailing while your there ! Considering how close everything is the street is very quiet and the owners were great to deal with. Thanks Kathi and Grant!

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$501

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

Responds fast! avg. 4 minutes

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Price per night from

$221

Palm Bay on Private Beach, WiFi, Full Beach Views

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great condo” Loved it. Modern, beachy, clean, well equipped. Excellent location on the beach. Would definitely stay again.

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Price per night from

$321

Midcentury modern pool home on Siesta Key w/ gorgeous backyard

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$303

Steps to Siesta Key Beach, Pool/Spa/Tiki Bar

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$316

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Price per night from

$229

Competitive Rates, Palm Bay Private Beach, Pools

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$207

Private Beach, Lit Tennis/Pickle, 2 Heated Pools

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$168

Lower Pricing! Private Beach, Pools, Bay Sunrises

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$197

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

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$904

Ten35 Seaside - Direct Gulf View: Residence 405

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$860

Ten35 Seaside - Direct Gulf View: Residence 303

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$860

Ten35 Seaside - Direct Gulf View: Residence 403

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$860

Ten35 Seaside - Direct Gulf View: Residence 301

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$860

Responds fast! avg. 4 minutes

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Price per night from

$103

Ten35 Seaside - Direct Gulf View: Residence 501

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$951

Dream beach, pool/spa retreat!

Siesta Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$345

Siesta key Guest House 5 star on the water Private

Siesta Key guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$230

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

Las Palmas; by Beachside Management

Siesta Key house

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

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Price per night from

$1,204

Magnificent Bayfront Condo - Resort Living on the Bay

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$161

$185 Free Activities Daily, Beach Complex, Gated, Heated Pool, Garden View

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$232

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

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

$860

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

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$490

Ten35 Seaside - Island View: Residence 308

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$550

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 - South Water View: Residence 602

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$688

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

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$490

Ten35 Seaside - South Water View: Residence 302

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Clothes dryer Jacuzzi or hot tub

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Price per night from

$607

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