Houses Longboat Key

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726 houses

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Rental types Staffed property Golf course on site or within 15 min walk Tennis in town

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Price per night from

$149

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3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Tennis in town

3 of 4 filters match

Price per night from

$287

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Tennis in town, Staffed property

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Price per night from

$436

+++ Clean & Bright +++ Minutes to Anna Maria Island

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Tennis in town, Staffed property

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Price per night from

$178

Cozy & Bright+++Minutes to Anna Maria Island, IMG Academy and more

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Tennis in town, Staffed property

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Price per night from

$117

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“It was very cozy and comfortable apartment!” We loved to spend our vacation at this place. Really close to the beach, to different restaurants, and all kind of stores.

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Tennis in town, Staffed property

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Price per night from

$115

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

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Tennis in town, Staffed property

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Price per night from

$745

Anna Maria Island Beach Watch

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Tennis in town

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Price per night from

$250

Anna Maria Island Beach Happy-Direct Beach Front-1BR-1BR

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Tennis in town

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Price per night from

$228

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Tennis in town, Staffed property

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Price per night from

$284

Stunning & Serene +++ Minutes from Anna Maria Island, IMG Academy and more!

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Tennis in town, Staffed property

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Price per night from

$114

Responds fast! avg. 11 minutes

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Tennis in town, Staffed property

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Price per night from

$132

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Tennis in town

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Price per night from

$108

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Tennis in town

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Price per night from

$229

Anna Maria Island Beach Palace

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Tennis in town

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Price per night from

$595

Anna Maria Island Beach Haven

Cortez house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Tennis in town

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Price per night from

$1,500

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

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Tennis in town

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Price per night from

$385

Anna Maria Beach Serenity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Tennis in town

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Price per night from

$950

Beautiful Longboat Key Home!

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 27 minutes

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Tennis in town

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Price per night from

$516

Anna Maria Island Sun's Up B

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Tennis in town

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Price per night from

$480

Anna Maria Island Sun's Up A

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Tennis in town

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Price per night from

$495

Anna Maria Island Edgewater Bungalow

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Tennis in town

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Price per night from

$297

Anna Maria Island Surfside Bungalow

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Tennis in town

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Price per night from

$355

Gorgeous Pool Home. 12 min from the beaches of Anna Maria, IMG

Bradenton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Tennis in town

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Price per night from

$281

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

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Tennis in town

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Price per night from

$286

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.

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Tennis in town

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Price per night from

$476

#7 Loft Apartment in Historic District Downtown Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Tennis in town

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Price per night from

$305

AMI Lighthouse Cottage-One Minute Walk To The Beach-Keyless Locks

Cortez cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Tennis in town

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Price per night from

$164

Siesta Key Beach : 2 Bedroom, 3 Beds, 3 Bathroom Duplex & Heated Pool

Siesta Key apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Tennis in town

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Price per night from

$182

Blue Lagoon; By Beachside Management

Siesta Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 4 match: Golf course on site or within 15 min walk, Staffed property, Rental types, Tennis in town

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Price per night from

$411

Come Sail A Bay

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Golf course on site or within 15 min walk, Staffed property, Rental types, Tennis in town

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Price per night from

$264

Kai Blue

Holmes Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 4 match: Golf course on site or within 15 min walk, Staffed property, Rental types, Tennis in town

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Price per night from

$457

Costa Lotta

Holmes Beach house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

2 of 4 match: Golf course on site or within 15 min walk, Staffed property, Rental types, Tennis in town

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Price per night from

$501

L'Oasis East

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 4 match: Golf course on site or within 15 min walk, Staffed property, Rental types, Tennis in town

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Price per night from

$186

L'Oasis West

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 4 match: Golf course on site or within 15 min walk, Staffed property, Rental types, Tennis in town

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Price per night from

$186

Kokomo

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Golf course on site or within 15 min walk, Staffed property, Rental types, Tennis in town

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Price per night from

$234

Island Haven

Holmes Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 4 match: Golf course on site or within 15 min walk, Staffed property, Rental types, Tennis in town

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Price per night from

$439

Surfer's Dream

Holmes Beach house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 8

2 of 4 match: Golf course on site or within 15 min walk, Staffed property, Rental types, Tennis in town

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Price per night from

$636

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rentals in Longboat Key

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