Houses Longboat Key

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Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Rental types Staffed property Golf course on site or within 15 min walk Pets allowed

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Price per night from

$150

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White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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

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Price per night from

$631

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, Staffed property, Pets allowed

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Price per night from

$115

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

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Price per night from

$287

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, Pets allowed

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Price per night from

$396

Beautiful Longboat Key Home!

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 27 minutes

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

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Price per night from

$517

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

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Price per night from

$108

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

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Price per night from

$230

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

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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

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Price per night from

$287

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, Pets allowed

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Price per night from

$281

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$178

#7 Loft Apartment in Historic District Downtown Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$306

March 23-March 30, 2024 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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

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Price per night from

$746

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, Pets allowed, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$117

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

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Price per night from

$285

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, Pets allowed, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$114

Mid Century Home With Private Heated Pool

Tallevast house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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

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Price per night from

$183

Responds fast! avg. 0 minutes

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

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Price per night from

$230

Responds fast! avg. 11 minutes

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

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Price per night from

$132

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, Pets allowed

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Price per night from

$191

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

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

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Price per night from

$2,294

Anna Maria Island Beach Watch

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

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

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

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

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Price per night from

$1,503

Rare Castle Style Stay! Downtown

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$213

Anna Maria Island Edgewater Bungalow

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

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

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Price per night from

$296

Anna Maria Island Beach Palace

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

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

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Price per night from

$597

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

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Price per night from

$478

Anna Maria Island Surfside Bungalow

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

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

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

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Price per night from

$497

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

2 of 4 filters match

Price per night from

$386

Anna Maria Beach Serenity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

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

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Price per night from

$951

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 57 minutes

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

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Price per night from

$194

Tiny House Siesta - Sand Dollar – A private master loft and open living space

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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

2 of 4 filters match

Price per night from

$448

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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

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Price per night from

$234

Spacious Apt. #1 Historic Walkable Downtown, between Siesta & Lido Beach

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$483

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.

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

2 of 4 filters match

Price per night from

$477

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rentals in Longboat Key

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