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Another Day in Paradise

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 1 minutes

Match: Rental types Skiing – property near ski resort

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Price per night from

$542

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Downtown Sarasota five star home

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$194

Charming Artist's Cottage In Laurel Park

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$143

Convenient + Cozy + Quite + Comfortable :-)

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 17 minutes

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$314

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Skiing – property near ski resort, Rental types

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Price per night from

$995

Venice Island Bellagio Home w/ 3BR & 3BA

Venice house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Great Vacation” Thanks for allowing us to stay in your beautiful home in Venice Florida. It was very comfortable and had all the convenience of home. Everything we needed was close by (restaurants and grocery store). We really liked the bike trails along the canal since we brought our bikes. We would rent your house again.

1 of 2 match: Skiing – property near ski resort, Rental types

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Price per night from

$103

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: Skiing – property near ski resort, Rental types

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Price per night from

$499

A Wonderful Pool House on a lake full of wildlife.

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Location location” Great house convincent , clean , close to everything

1 of 2 match: Skiing – property near ski resort, Rental types

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Price per night from

$121

Three bedroom house directly on beach with gulf vi

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$400

Charming Lido Key Beach House 5 min Walk to Beach!

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Skiing – property near ski resort, Rental types

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Price per night from

$408

****Walk to Beach-5min! Waterfront Canal! Private Pool~spa~Kayaks, Bikes!

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$452

Oceanfront home w/sunset views of Sarasota Bay

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$627

Renovated Beach Front 2BR/2BA Condo, Steps to beach, Gulf of Mexico Views

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Skiing – property near ski resort, Rental types

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Price per night from

$276

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: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$999

CKBH (Casey Key Beach House)

Osprey house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Skiing – property near ski resort, Rental types

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Price per night from

$652

Downtown Sarasota Historic Burns Court Adorable Bungalow

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$294

Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“What a great view” We usually rent a house one block from the main Siesta Key beach area. This year friends rented the house and my husband and I stayed in this condo for a week. Loved the view of the beach from the living room! Loved the lani! Location was great. Pool was massive compared to our usual house pool, however we did have to walk thru parking lot to get there. The noise from the hall was annoying. And I did miss my temperpedic mattress, but had a great relaxing time.

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$327

Lakefront Oasis 3 Bdrm House with Heated Pool minutes from village and beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$685

1 of 2 match: Skiing – property near ski resort, Rental types

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Price per night from

$132

Tiny House Siesta - Tiny House Amy

Siesta Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$376

Tiny House Siesta - Red Lifeguard Stand

Siesta Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$441

#1 EXCLUSIVE Siesta Key Beach House /3 payments

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$257

Tiny House - Margarita

Gulf Gate Branch house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$468

Tiny House - Blue Lifeguard Stand

Gulf Gate Branch house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$420

Tiny House - Flamingo

Gulf Gate Branch house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$397

Tiny House - The Siesta

Gulf Gate Branch house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$372

Tiny House - Green Lifeguard Stand

Gulf Gate Branch house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$462

Tiny House - Seashell

Gulf Gate Branch house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$313

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

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$2,840

Hidden gem close to everything

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 16 minutes

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$216

Oceanfront home

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$684

New York Avenue Rancher

Gulf Gate Estates house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$443

BeautifulHome with Pool - 3 miles from Siesta Key Beach

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 38 minutes

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$240

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$343

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$182

5 min to the Beach, Sleeps 6

Nokomis house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$136

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$571

1 of 2 match: Skiing – property near ski resort, Rental types

1 of 2 filters match

Price per night from

$273

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