Houses Longboat Key

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436 houses

Anna Maria Island/ IMG Academy/ Beach/ HotTub/ Bikes/ Kayaks/ Golf/ Fishing

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$287

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Sarasota Rambler | Downtown MidMod Stay

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$315

Downtown Sarasota Historic Burns Court Adorable Bungalow

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$295

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$108

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$295

Super Cute Cottage--Private--Walk/Bike to Beach

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$258

Stay near the beach and downtown

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$69

Three bedroom house directly on beach with gulf vi

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

2 of 3 match: Trampoline, Rental types, Bicycles available

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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

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$368

Charming Lido Key Beach House 5 min Walk to Beach!

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$410

Luxury Modern Oasis in Heart of Sarasota

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$1,032

Beautiful Longboat Key Home!

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 27 minutes

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$517

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$631

2BR/2BA House Just Steps to Siesta Village & Siesta Key Beach

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Location, Very Well Appointed” This house is perfectly located right in Siesta Key Village within an easy walk to shops and restaurants. It is also just a block from the beach. No parking hassles! The house is very well appointed. The owner has thoughtfully provided more than enough coffee for the Keurig, lots of towels, and all needed kitchen utensils, dishes, containers, and cooking supplies, in addition to a beach wagon and chairs. Although not luxurious, this is a very comfortable rental. We also liked the privacy of having our own house. The only negatives were the lack of towel racks in the bathrooms and the lack of hot water in the bathroom with the tub (it remained only warm, even after running for a very long time). The water in the other bathroom was fine.

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$315

Cloud 9

Anna Maria house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 8

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$1,947

Tripletail

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$1,718

Lookout: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 10

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$743

Blue Lagoon; By Beachside Management

Siesta Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$411

Off the Hook: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$514

Buena Vida: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$514

Siesta Dunes #300: By Beachside Management

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$331

Fanta-Sea 49: By Beachside Management

Siesta Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$858

Responds fast! avg. 0 minutes

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$229

NW Bradenton Exectitive Home

Bradenton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$493

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!

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$501

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

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$689

Waves on Anna Maria

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$976

Mintfish

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$1,145

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$457

Enjoy our Beach, Pool and Dock! 100 5-Star Reviews!

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$743

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.

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$476

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$1,260

Serendipity Deux- Beachfront 4 Bed/heated pool/elevator

Anna Maria house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$2,290

Las Palmas; by Beachside Management

Siesta Key house

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$1,201

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

2 of 3 match: Trampoline, Rental types, Bicycles available

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Price per night from

$149

Newly Remodeled Spacious Loft in Sarasota!

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Trampoline, Bicycles available

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Price per night from

$295

🏝Paradise on the Sarasota Bay, Close to Gulf Beaches🏝 (Sarasota)

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 3 match: Rental types, Trampoline, Bicycles available

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Price per night from

$194

1 of 3 match: Rental types, Trampoline, Bicycles available

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Price per night from

$138

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rentals in Longboat Key

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