Vacation Rentals & Beach Rentals in Siesta Key

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45 beach rentals

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$272

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,000

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!

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$273

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!

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$501

GULF FRONT ON #1 Beach! Siesta Dunes (by owner)

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Perfect, Perfect, Perfect” Nice condo with everything close by! Owners were great to deal with and as stated it would be . We plan on visiting again and would recommend this place to anyone.

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$272

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

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$904

Dream beach, pool/spa retreat!

Siesta Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$344

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$490

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$490

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$490

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$490

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$490

Split Leaf at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$490

Coconut at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$490

Responds fast! avg. 4 minutes

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$229

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

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$316

Siesta key Guest House 5 star on the water Private

Siesta Key guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$230

Magnificent Bayfront Condo - Resort Living on the Bay

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$161

Ten35 Seaside - North Water View: Residence 606

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$779

Ten35 Seaside - Island View: Residence 406

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$561

Ten35 Seaside - South Water View: Residence 502

Siesta Key condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$756

Ten35 Seaside - North Water View: Residence 506

Siesta Key condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$779

Ten35 Seaside - South Water View: Residence 302

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$607

Ten35 Seaside - Island View: Residence 604

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$561

Ten35 Seaside - North Water View: Residence 310

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

Ten35 Seaside - Direct Gulf View: Residence 303

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$859

Ten35 Seaside - Direct Gulf View: Residence 307

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$859

Ten35 Seaside - Direct Gulf View: Residence 301

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$859

Ten35 Seaside - North Water View: Residence 410

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

Ten35 Seaside - Island View: Residence 408

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$550

Ten35 Seaside - Direct Gulf View: Residence 501

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$951

Ten35 Seaside - Direct Gulf View: Residence 405

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$859

Ten35 Seaside - South Water View: Residence 602

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$687

Ten35 Seaside - Direct Gulf View: Residence 403

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$859

Ten35 Seaside - Island View: Residence 308

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$550

Las Palmas; by Beachside Management

Siesta Key house

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,203

Competitive Rates, Palm Bay Private Beach, Pools

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 4 minutes

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$207

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

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 4 minutes

1 of 2 match: Private fishing lake or river, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$317

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