Houses Longboat Key

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421 houses

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

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Rental types Safe Walking trips

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Price per night from

$344

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

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Safe Walking trips

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Price per night from

$287

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Rental types Safe Walking trips

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Price per night from

$149

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Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$430

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

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Price per night from

$138

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN CONDO!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$272

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: Safe, Rental types, Walking trips

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Price per night from

$249

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: Safe, Rental types, Walking trips

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Price per night from

$231

Anna Maria Island Beach Haven

Cortez house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

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

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Price per night from

$1,503

Anna Maria Beach Serenity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

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

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Price per night from

$952

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: Safe, 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: Safe, Rental types, Walking trips

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Price per night from

$356

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: Safe, Rental types, Walking trips

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Price per night from

$492

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: Safe, Rental types, Walking trips

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Price per night from

$386

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: Safe, Rental types, Walking trips

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Price per night from

$591

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: Safe, Rental types, Walking trips

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Price per night from

$473

Three bedroom house directly on beach with gulf vi

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

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

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Price per night from

$367

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

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Price per night from

$295

The Pink Riverhouse-

Ellenton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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

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Price per night from

$688

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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

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Price per night from

$1,262

TROPICCAL, 4 min from the beaches! Meticulously cleaned and sanitized!

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

“Lovely home in an awesome location!” Literally a minute's drive from the beach, this very clean and welcoming home is also convenient to great restaurants and shopping opportunities. It really is in a perfect location, especially considering the affordable price. Walking to restaurants and a rental shop is easy thanks to the sidewalk on Cortes. We even enjoyed a morning run to the beach - biking to the beach would also be a great option (3.5 mi one way.) The home might appear small at first, but we fit 6 comfortably, including 4 teenagers! The best part is the lovely décor that greets you after a long day at the beach or running around. Two thumbs up!

Responds fast! avg. 2 hours 28 minutes

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

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Price per night from

$144

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, Safe, Walking trips

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Price per night from

$101

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, Safe, Walking trips

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Price per night from

$239

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, Safe, Walking trips

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Price per night from

$164

#1 EXCLUSIVE Siesta Key Beach House /3 payments

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

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Price per night from

$258

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

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Price per night from

$183

Siesta Key Waterfront Estate heated Pool Privacy!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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

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Price per night from

$717

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

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Price per night from

$144

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, Safe, Walking trips

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Price per night from

$166

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, Safe, Walking trips

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Price per night from

$510

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, Safe, Walking trips

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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

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

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Price per night from

$780

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

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Price per night from

$138

“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, Safe, Walking trips

1 of 3 filters match

Price per night from

$144

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

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

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Price per night from

$328

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

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

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Price per night from

$192

Anna Maria Island Beach Bay Breeze

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

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

1 of 3 filters match

Price per night from

$190

Viewing 38 of 421
rentals in Longboat Key

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