Houses Longboat Key

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660 houses

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

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Rental types Boat available Private outdoor pool (heated)

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Price per night from

$745

Anna Maria Island Beach Palace

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

Match: Rental types Boat available Private outdoor pool (heated)

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Price per night from

$597

Anna Maria Beach Serenity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

Match: Rental types Boat available Private outdoor pool (heated)

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Price per night from

$951

Anna Maria Island Sun's Up B

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

Match: Rental types Boat available Private outdoor pool (heated)

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Price per night from

$478

Anna Maria Island Sun's Up A

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

Match: Rental types Boat available Private outdoor pool (heated)

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Price per night from

$497

Anna Maria Island Edgewater Bungalow

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Rental types Boat available Private outdoor pool (heated)

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Price per night from

$296

Anna Maria Island Surfside Bungalow

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Rental types Boat available Private outdoor pool (heated)

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Price per night from

$356

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Anna Maria Island Beach Paradise 10

Holmes Beach studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$228

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 3 match: Rental types, Boat available, Private outdoor pool (heated)

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Price per night from

$781

Anna Maria Island Retreat

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

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Price per night from

$226

Bradenton Beach Club Bliss-3 Bedroom-2 Bathroom Condo-2 Pools-HotTub-Private Bea

Bradenton Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

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Price per night from

$259

Anna Maria Island Beach Palms 7A

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$192

Anna Maria Island Beach Palms 2A

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

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Price per night from

$189

Paradise Palms-Private Beach Access-Heated Pool-Water Views From Every Room

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

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Price per night from

$231

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 3 match: Rental types, Boat available, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$333

Anna Maria Island Beach Palms 2B

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

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Price per night from

$248

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 3 match: Rental types, Boat available, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$189

Anna Maria Island Beach Waves

Cortez condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$216

Anna Maria Island Beach View 207

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$187

Anna Maria Island Bridge Port Beach Resort

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$177

Anna Maria Island Runaway Tropical Escape

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$208

Anna Maria Island Beach Sands 201

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$287

Anna Maria Island Beach Palms 8B

Cortez condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$193

Absolute Paradise AMI-Private Beach Access-Water Views From Every Window-Heated

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$265

Paradise 3 Bedroom Pool Home Close to Siesta Key Beach and IMG Academy

Braden River house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 9 minutes

2 of 3 match: Boat available, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$373

2 of 3 match: Boat available, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$574

Glorious Daze 4bedroom/4bath beachfront home with golf cart & elevator!

Holmes Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Boat available, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$1,377

Castaway Cottage

Holmes Beach house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Boat available, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$390

Remodeled 4BR Pool Home / Golf View/Near Beaches

South Bradenton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

2 of 3 match: Boat available, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$517

Coastal Paradise! 5 mi to beaches! Heated Pool! Sleep up to 14

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

2 of 3 match: Boat available, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$1,257

FantaSea

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Boat available, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$1,492

THE LIDO RESIDENCE

Lido Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

2 of 3 match: Boat available, Rental types, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$779

Unit #102 Sand Cay Beach Resort Gulf Front

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$343

Unit #110 Sand Cay Beach Pool and Garden View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$279

Unit #211 Sand Cay Beach Resort Pool and Garden View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$279

Unit #113 Sand Cay Beach Resort Pool and Garden View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$279

Anna Maria Island Bay Watch Bungalow

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$241

Anna Maria Island Beach Palms 5B

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Rental types, Boat available, Private outdoor pool (heated)

2 of 3 filters match

Price per night from

$241

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