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 Secure parking

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Price per night from

$149

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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

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

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Price per night from

$117

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, Secure parking

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Price per night from

$115

Responds fast! avg. 0 minutes

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

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Price per night from

$229

Responds fast! avg. 11 minutes

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

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Price per night from

$132

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

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Price per night from

$284

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, Secure parking

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Price per night from

$476

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, Secure parking

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Price per night from

$287

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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Price per night from

$344

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, Secure parking

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Price per night from

$281

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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

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Price per night from

$205

Siesta Key Beach : 2 Bedroom, 3 Beds, 3 Bathroom Duplex & Heated Pool

Siesta Key apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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

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Price per night from

$182

Rambo's Beach Retreat! Tradewinds Unit 14

Bradenton Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$453

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

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Price per night from

$148

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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

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Price per night from

$630

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$178

Shorewalk waterfront Condo Bradenton

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Nice and affordable condo convenient to shopping and restaurants.” This unit has been updated and is a very comfortable place to stay. The owner responded promptly when we contacted him.

Responds fast! avg. 2 hours 1 minutes

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

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Price per night from

$95

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, Secure parking, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$745

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, Secure parking, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$114

120 Steps to the Beach with beach gear included!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 4 filters match

Price per night from

$424

Mid Century Home With Private Heated Pool

Tallevast house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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

2 of 4 filters match

Price per night from

$182

Stunning & Bright Sarasota Home

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 4 filters match

Price per night from

$395

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

2 of 4 filters match

Price per night from

$287

Jamaica Royale #104! Completely renovated, Gulf side, beautiful 2b/2b Condo!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 4 filters match

Price per night from

$337

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

2 of 4 filters match

Price per night from

$409

Banana Cabana: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 4 filters match

Price per night from

$240

Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.

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

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Price per night from

$189

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

2 of 4 filters match

Price per night from

$192

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, Secure parking, Rental types, Golf course on site or within 15 min walk

2 of 4 filters match

Price per night from

$250

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, Secure parking, Rental types, Golf course on site or within 15 min walk

2 of 4 filters match

Price per night from

$229

Ten35 Seaside - Island View: Residence 308

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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

2 of 4 filters match

Price per night from

$549

Ten35 Seaside - Island View: Residence 408

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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

2 of 4 filters match

Price per night from

$549

Ten35 Seaside - Island View: Residence 604

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

2 of 4 filters match

Price per night from

$560

Ten35 Seaside - Island View: Residence 406

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

2 of 4 filters match

Price per night from

$560

Ten35 Seaside - South Water View: Residence 502

Siesta Key condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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

2 of 4 filters match

Price per night from

$755

Ten35 Seaside - North Water View: Residence 606

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

2 of 4 filters match

Price per night from

$778

Ten35 Seaside - North Water View: Residence 506

Siesta Key condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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

2 of 4 filters match

Price per night from

$778

Viewing 38 of 610
rentals in Longboat Key

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