Houses Longboat Key

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Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$149

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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, Satellite TV, 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, Satellite TV, 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, Satellite TV, Staffed property

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Price per night from

$745

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Price per night from

$285

Mid Century Home With Private Heated Pool

Tallevast house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Satellite TV

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Price per night from

$183

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Satellite TV

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Price per night from

$287

Responds fast! avg. 12 minutes

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Satellite TV, Staffed property

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Price per night from

$144

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, Satellite TV

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Price per night from

$255

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, Satellite TV

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Price per night from

$235

Anna Maria Island Beach Haven

Cortez house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

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Price per night from

$1,502

Anna Maria Island Edgewater Bungalow

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

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Price per night from

$303

Anna Maria Island Surfside Bungalow

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

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Price per night from

$415

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, Satellite TV

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Price per night from

$467

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, Satellite TV

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Price per night from

$494

Anna Maria Island Beach Palace

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

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Price per night from

$571

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, Satellite TV

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Price per night from

$385

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Satellite TV

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Price per night from

$230

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, Satellite TV

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Price per night from

$1,145

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Satellite TV, Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$631

Classic Tropical Florida Escape with Pool

Pinecraft house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Satellite TV, Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$298

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Satellite TV, Golf course on site or within 15 min walk, 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

2 of 4 match: Rental types, Satellite TV, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$178

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, Satellite TV

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Price per night from

$476

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, Satellite TV

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Price per night from

$281

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, Satellite TV

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Price per night from

$171

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, Satellite TV

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Price per night from

$182

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

2 of 4 match: Rental types, Satellite TV, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$114

Responds fast! avg. 0 minutes

2 of 4 match: Satellite TV, Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$230

Stunning & Bright Sarasota Home

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Satellite TV, Staffed property, Rental types, Golf course on site or within 15 min walk

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Price per night from

$395

Cottage Haven-One Minute Walk To The Beach-Private Yards-Keyless Locks

Cortez cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Satellite TV

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Price per night from

$219

Anna Maria Island Beach Paradise 10

Holmes Beach studio

  • Studio
  • 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, Satellite TV

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Price per night from

$227

Anna Maria Island Martinique On The Beach

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Satellite TV

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Price per night from

$780

Anna Maria Island Beach Sands

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Paradise” We loved this place, felt right at home the minute we walked in the door. Had a view minor problems and the service to deal with them was awesome. Thanks Terry for a great experience, being our first time here on anna Maria Island. If we didn't need the extra bedroom, we would have booked for next yr. Location~~!! wow, close to great restaurants Love the view...can't say enough of the sunsets and of course the dolphins, got chills every time I seen them, almost daily...first class...thanks...

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Satellite TV

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Price per night from

$336

Anna Maria Island Beach Palms 8B

Cortez condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Satellite TV

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Price per night from

$193

Anna Maria Island Runaway Tropical Escape

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Satellite TV

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Price per night from

$202

Gulf Breeze Ami-2BD-2BA-Condo-Private Beach Access-Heater Pool-Water Views From

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Satellite TV

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Price per night from

$192

Longboat Key Cedars Beach House-Pet Friendly-2 Minute To The Beach

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Satellite TV

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Price per night from

$195

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rentals in Longboat Key

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