Houses Longboat Key

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432 houses

Newly renovated beach house near AMI free trolley stop with Private pool

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Rental types Table tennis Sea view

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Price per night from

$561

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Rental types Table tennis Sea view

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Price per night from

$1,260

Las Palmas; by Beachside Management

Siesta Key house

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

Match: Rental types Table tennis Sea view

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Price per night from

$1,202

Waves on Anna Maria

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Rental types Table tennis Sea view

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Price per night from

$974

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Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Table tennis, Sea view

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Price per night from

$229

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Table tennis, Sea view

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Price per night from

$436

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

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Table tennis, Sea view

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Price per night from

$903

Florida Palms Heaven 2B Villa, near tennis IMG Academy & beaches

South Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Table tennis, Sea view

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Price per night from

$148

Beachfront Condo Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!

2 of 3 match: Rental types, Table tennis, Sea view

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Price per night from

$453

Family Reunion Villa on Anna Maria Island, Florida

Bradenton Beach villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

2 of 3 match: Rental types, Table tennis, Sea view

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Price per night from

$573

March 23-March 30, 2024 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Table tennis, Sea view

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Price per night from

$745

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

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Sea view, Rental types, Table tennis

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Price per night from

$258

Luxury Modern Oasis in Heart of Sarasota

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Sea view, Rental types, Table tennis

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Price per night from

$1,030

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

2 of 3 match: Sea view, Rental types, Table tennis

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Price per night from

$2,289

Beautiful Longboat Key Home!

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 27 minutes

2 of 3 match: Sea view, Rental types, Table tennis

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Price per night from

$516

Off the Hook: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Sea view, Rental types, Table tennis

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Price per night from

$515

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: Sea view, Rental types, Table tennis

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Price per night from

$476

Near Img And Siesta Key Beach Paradise Home

Oneco house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Table tennis, Rental types, Sea view

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Price per night from

$361

AMI Gulf Lookout-Views Of The Gulf From Every Room-Rooftop Terrace

Cortez house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Table tennis, Rental types, Sea view

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Price per night from

$385

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Sea view, Table tennis

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Price per night from

$489

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Sea view, Table tennis

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Price per night from

$489

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Sea view, Table tennis

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Price per night from

$489

Beach Dreams "Tangerine Dreams Villa "

Bradenton Beach cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 3 match: Rental types, Table tennis, Sea view

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Price per night from

$344

Three bedroom house directly on beach with gulf vi

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

2 of 3 match: Table tennis, Rental types, Sea view

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Price per night from

$401

Fanta-Sea 49: By Beachside Management

Siesta Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

2 of 3 match: Table tennis, Rental types, Sea view

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Price per night from

$858

Another Day in Paradise

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 1 minutes

2 of 3 match: Table tennis, Rental types, Sea view

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Price per night from

$544

Beachfront Paradise w/ Private Beach, Dogs Stay Free, Beach in Backyard

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Table tennis, Rental types, Sea view

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Price per night from

$630

Lookout: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 10

2 of 3 match: Table tennis, Rental types, Sea view

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Price per night from

$744

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

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Table tennis, Rental types, Sea view

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Price per night from

$277

Anna Maria Beach Serenity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Table tennis, Rental types, Sea view

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Price per night from

$950

SPECIAL! $650 8/24 - 8/31. PRIME LOCATION AMI DIRECTLY ON BEACH HEATED POOL

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Table tennis, Rental types, Sea view

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Price per night from

$287

Beach Dreams "DreamBoat Villa"

Bradenton Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 3 match: Rental types, Table tennis, Sea view

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Price per night from

$487

Rare Castle Style Stay! Downtown

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Table tennis, Rental types, Sea view

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Price per night from

$212

Cloud 9

Anna Maria house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 8

2 of 3 match: Table tennis, Rental types, Sea view

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Price per night from

$1,947

Tripletail

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Table tennis, Rental types, Sea view

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Price per night from

$1,718

Beachplace Building 3 unit 302

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Sea view, Table tennis

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Price per night from

$187

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Sea view, Table tennis

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Price per night from

$489

Coconut at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Sea view, Table tennis

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Price per night from

$489

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rentals in Longboat Key

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