Houses Longboat Key

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374 houses

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

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Trampoline Walking trips

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Price per night from

$287

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Anna Maria Island Beach Watch

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Trampoline, Rental types, Walking trips

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Price per night from

$251

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

2 of 3 match: Trampoline, Rental types, Walking trips

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Price per night from

$232

Anna Maria Island Beach Haven

Cortez house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Trampoline, Rental types, Walking trips

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Price per night from

$1,503

Great Townhouse Very Close to the Beach, Shops, and Restaurants

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Trampoline, Rental types, Walking trips

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Price per night from

$344

Anna Maria Island Sun's Up A

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Trampoline, Rental types, Walking trips

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Price per night from

$495

Anna Maria Island Sun's Up B

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Trampoline, Rental types, Walking trips

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Price per night from

$477

Anna Maria Island Edgewater Bungalow

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Trampoline, Rental types, Walking trips

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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

2 of 3 match: Trampoline, Rental types, Walking trips

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Price per night from

$355

Anna Maria Island Beach Palace

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Trampoline, Rental types, Walking trips

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Price per night from

$596

Anna Maria Beach Serenity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

2 of 3 match: Trampoline, Rental types, Walking trips

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Price per night from

$951

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: Trampoline, Rental types, Walking trips

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Price per night from

$385

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, Walking trips

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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, Walking trips

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Price per night from

$368

The Pink Riverhouse-

Ellenton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Trampoline, Rental types, Walking trips

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Price per night from

$689

2 of 3 match: Trampoline, Rental types, Walking trips

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Price per night from

$295

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Trampoline, Rental types, Walking trips

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Price per night from

$1,260

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

2 of 3 match: Trampoline, Rental types, Walking trips

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Price per night from

$149

Steps to beach and bay on beautiful Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 3 match: Rental types, Trampoline, Walking trips

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Price per night from

$101

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

1 of 3 match: Rental types, Trampoline, Walking trips

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Price per night from

$164

Anna Maria Island Bay Watch Bungalow

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 20 minutes

1 of 3 match: Rental types, Trampoline, Walking trips

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Price per night from

$240

Luxurious 2 BR Condo-Short Walk to Siesta Beach/1 Small Dog (25 lbs Max) Allowed

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“a fine 2 weeks in Siesta” charming property, that was comfortable for four. The unit was very clean and fresh upon arrival. The neighbours were friendly and the overall property well kept. Siesta Key is a quiet community with usual shopping amenities over the causeway. This property was a brief 10 minute walk to the beach. Would we stay again, yes.

1 of 3 match: Rental types, Trampoline, Walking trips

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Price per night from

$166

Anna Maria Island Beach Paradise 10

Holmes Beach studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

1 of 3 match: Rental types, Trampoline, Walking trips

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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

1 of 3 match: Rental types, Trampoline, Walking trips

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Price per night from

$781

1 of 3 match: Rental types, Trampoline, Walking trips

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Price per night from

$138

1 of 3 match: Rental types, Trampoline, Walking trips

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Price per night from

$138

1 of 3 match: Rental types, Trampoline, Walking trips

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Price per night from

$144

“Clean comfortable Siesta Key Condo with all the comforts of home...Perfect!” The condo is walking distance to shops, restaurants and quaint local tiki bar! The beach is a short walk across the street and through the beach-front section of the complex with lounge chairs and umbrellas available, very nice! I didn't mention the 2 pools (one beachside) and nice gym facilities also just downstairs of the unit. The covered parking space was an added plus! The condo was clean and very comfortable with all of the amenities of home which is greatly appreciated! You can even enjoy the view of the bayside inlet and beautiful landscaping from the kitchen through the entire wall of glass doors in the living/dining room! We had a wonderful week! The property owner Vic supplied more than enough information on the condo, local businesses and area maps! He was such a pleasure to work with! Thanks again Vic! We are already planning our next trip to Siesta Key in May!!

1 of 3 match: Rental types, Trampoline, Walking trips

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Price per night from

$144

Siesta Key private beach access

Siesta Key villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Siesta Key Townhouse” This was a wonderful place to stay! The house was very clean and spacious and had everything we needed for a week at the beach.

1 of 3 match: Rental types, Trampoline, Walking trips

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Price per night from

$509

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Trampoline, Walking trips

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Price per night from

$430

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

1 of 3 match: Rental types, Trampoline, Walking trips

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Price per night from

$264

Anna Maria Island Runaway Tropical Escape

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 3 match: Rental types, Trampoline, Walking trips

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Price per night from

$205

Anna Maria Island Beach Sands 201

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 3 match: Rental types, Trampoline, Walking trips

1 of 3 filters match

Price per night from

$287

Anna Maria Island Sunshine Kiss Villa

Holmes Beach studio

  • Studio
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 3 match: Rental types, Trampoline, Walking trips

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Price per night from

$152

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

1 of 3 match: Rental types, Trampoline, Walking trips

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Price per night from

$216

Anna Maria Island Beach Palms 8B

Cortez condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 3 match: Rental types, Trampoline, Walking trips

1 of 3 filters match

Price per night from

$192

Anna Maria Island Runaway Tropical Dream-One Minute Walk To The Beach-Heated Poo

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 3 match: Rental types, Trampoline, Walking trips

1 of 3 filters match

Price per night from

$217

Anna Maria Island Absolute Anna Maria-Private Beach Access-Heated Pool-Wi-Fi

Anna Maria Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“A little gem” Lovely condo, great views and ideally situated for restaurants and shopping (all within walking distance). Would definitely come back again.

Responds fast! avg. 3 hours 20 minutes

1 of 3 match: Rental types, Trampoline, Walking trips

1 of 3 filters match

Price per night from

$265

Viewing 38 of 374
rentals in Longboat Key

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