Houses Longboat Key

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734 houses

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Rental types Staffed property Private pool Golf course on site or within 15 min walk

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Price per night from

$150

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Stunning & Bright Sarasota Home

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$397

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, Private pool

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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, Private pool

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Price per night from

$288

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, Private pool

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Price per night from

$299

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, Private pool

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Price per night from

$469

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, Private pool

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Price per night from

$555

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, Private pool

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Price per night from

$468

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, Private pool

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Price per night from

$357

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

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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, Private pool

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Price per night from

$1,149

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, Private pool

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Price per night from

$478

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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

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Price per night from

$633

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, Private pool

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Price per night from

$282

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$437

+++ 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, Private pool, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$179

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, Private pool

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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

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

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Price per night from

$782

Anna Maria Island Beach Sands 203

Bradenton Beach apartment

  • 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, Private pool

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Price per night from

$213

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 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Private pool

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Price per night from

$244

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, Private pool

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Price per night from

$184

Anna Maria Island Beach Palms 2A

Bradenton Beach apartment

  • 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, Private pool

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Price per night from

$184

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, Private pool

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Price per night from

$323

Anna Maria Island Beach Sands 101

Bradenton Beach apartment

  • 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, Private pool

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Price per night from

$283

Anna Maria Island Retreat

Bradenton Beach apartment

  • 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, Private pool

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Price per night from

$208

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 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Private pool

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Price per night from

$229

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, Private pool

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Price per night from

$192

Anna Maria Island Beach View 207

Bradenton Beach apartment

  • 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, Private pool

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Price per night from

$181

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 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Private pool

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Price per night from

$171

Anna Maria Island Beach Sands 201

Bradenton Beach apartment

  • 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, Private pool

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Price per night from

$283

Anna Maria Island Beach Palms 2B

Bradenton Beach apartment

  • 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, Private pool

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Price per night from

$245

Anna Maria Island Beach Palms 6B

Bradenton Beach apartment

  • 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, Private pool

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Price per night from

$185

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, Private pool

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Price per night from

$191

Anna Maria Island Beach Palms 7A

Bradenton Beach apartment

  • 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, Private pool

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Price per night from

$168

Anna Maria Island Beach Waves

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, Private pool

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Price per night from

$223

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 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Private pool

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Price per night from

$236

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

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

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Price per night from

$118

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.

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

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Price per night from

$115

Viewing 38 of 734
rentals in Longboat Key

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