Houses Siesta Key

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A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect Luxury” Our 5-week stay at this vacation rental was absolutely perfect. The house was everything you could ask for and more. We have stayed in many vacation rentals in the last 20 or so years that we have been coming to anna Maria Island and I have to say this one was right at the top of the list. The kitchen was outfitted with everything you could want. The beds were very comfortable. The neighborhood was nice and quiet. Short walk to the beach. The owners were very nice to deal with and always responded quickly and were very warm and helpful. Definitely can recommend this vacation rental.

Match: Rental types Children's pool

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Price per night from

$476

Venice Immaculate RemodeledHome-2 Bdr/2 Bath-Pool-WIFl&CABLE-2 Miles to Beach

South Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Children's pool

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Price per night from

$172

Anna Maria Islands best location Heated pool Best prices!

Anna Maria Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Children's pool

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Price per night from

$859

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Townhouse in Resort Community of Gran Paradiso

Venice apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Children's pool

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Price per night from

$238

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Children's pool

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Price per night from

$224

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Rental types, Children's pool

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Price per night from

$206

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Rental types, Children's pool

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Price per night from

$192

*** SUPER SPECIAL RATES at Harbor Towers ***

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

1 of 2 match: Rental types, Children's pool

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Price per night from

$114

Beautiful Sunkst Cottage Bradenton Beach - AMI-Tropical Setting - Heated Pool

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Children's pool, Rental types

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Price per night from

$516

Spacious Home Built in 2014, 30' Pool, Large Lanai

Port Charlotte house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Rental types

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Price per night from

$190

Park Model with lanai, large deck, block from pool

Venice house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Rental types

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Price per night from

$121

Lovely Brandnew Pool Villa w/ Private Beach, WiFi

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Rental types

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Price per night from

$213

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Children's pool, Rental types

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Price per night from

$1,000

Vacation Home on Coral Sands Ct. Spring Special !

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Children's pool, Rental types

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Price per night from

$155

Lovely one story home on the water

Palmetto house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Rental types

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Price per night from

$459

Spectacular Beach House With GulfView Only Steps to a Pristine Beach

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Rental types

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Price per night from

$688

Beautiful Barrier Island Beach House with Pool, Spa and Dock - Walk 2 Beach!

Don Pedro Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

1 of 2 match: Children's pool, Rental types

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Price per night from

$597

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: Children's pool, Rental types

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Price per night from

$104

BEAUTIFUL HOME ON OYSTER CREEK DRIVE ENGLEWOOD FL

Englewood house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Rental types

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Price per night from

$153

Spectacular view overlooking Oyster Creek

Englewood house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Rental types

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Price per night from

$316

Gorgeous views,spectacular home!

Anna Maria house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

“Majestic Views” Our family loved our visit to Anna Maria. The house is gorgeous and spacious. My kids enjoyed the pool and eating outside. We hope to return in the near future.

1 of 2 match: Children's pool, Rental types

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Price per night from

$631

Jacaranda Artist Retreat

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Rental types

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Price per night from

$218

Vacation Home on Alligator Drive . Winter 2025 Special !

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Children's pool, Rental types

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Price per night from

$149

ISLAND TOWNHOUSE - 200 Steps to the BEACH

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 43 minutes

1 of 2 match: Children's pool, Rental types

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Price per night from

$207

1 of 2 match: Children's pool, Rental types

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Price per night from

$230

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: Children's pool, Rental types

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Price per night from

$122

Responds fast! avg. 54 minutes

1 of 2 match: Children's pool, Rental types

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Price per night from

$268

Three bedroom house directly on beach with gulf vi

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

1 of 2 match: Children's pool, Rental types

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Price per night from

$402

BAY VIEW. SUNSETS. CLOSE TO ANNA MARIA ISLAND AND IMG ACADEMY

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Rental types

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Price per night from

$367

LEMON BAY COTTAGE

Englewood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect family cottage in Lemon Bay” Such a great little house and surprisingly bigger than pictures reveal. Perfect for a family with kids. 3rd toilet tucked away in laundry shed for easy access from pool. Great location as well, close to beaches, parks and many restaurants within walking distance. Definitely will rent there again. House was fresh, clean and inviting.

Responds fast! avg. 3 hours 37 minutes

1 of 2 match: Children's pool, Rental types

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Price per night from

$104

Luxury accommodation in Venetia, 3 months stay

Venice house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Rental types

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Price per night from

$192

Great Townhouse Very Close to the Beach, Shops, and Restaurants

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Rental types

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Price per night from

$344

Charming Lido Key Beach House 5 min Walk to Beach!

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Rental types

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Price per night from

$410

BAY FRONT HOUSE WITH PRIVATE DOCK

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 31 minutes

1 of 2 match: Children's pool, Rental types

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Price per night from

$344

6122

Englewood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Rental types

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Price per night from

$114

Manasota Beachy Cottage

Manasota Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“Our 2017 vacation” This was our first time ever renting a house. Peter was the best. This house had everything we need or wanted. It was super clean and beautiful. The screened porch was perfect to drink coffee in the morning. Didn't have to worry about the bugs or anything. Beach was a short walk around the corner over a bridge. The town was great and hardly no traffic. Safe for younger kids to play in the yard. Can't wait to rent again next year. Thank you!!

1 of 2 match: Children's pool, Rental types

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Price per night from

$155

Quiet pool home with lake view, close to beaches

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Rental types

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Price per night from

$230

Brand new villa with heated pool for swimmers

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Rental types

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Price per night from

$190

Viewing 38 of 457
rentals in Siesta Key

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