Houses Longboat Key

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653 houses

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 Car not required

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Price per night from

$149

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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

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Staffed property, Car not required

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Price per night from

$113

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, Car not required

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Price per night from

$117

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, Car not required

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Price per night from

$182

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, Car not required

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Price per night from

$481

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Staffed property, Car not required, Rental types, Golf course on site or within 15 min walk

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Price per night from

$628

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Staffed property, Car not required

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Price per night from

$229

Palm Bay Club - 343: By Beachside Management

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, Car not required

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Price per night from

$284

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Car not required, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$434

+++ 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, Car not required, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$177

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, Car not required

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Price per night from

$422

“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!!

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Staffed property, Car not required

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Price per night from

$143

Living the Dream - Pink Flamingo: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Staffed property, Car not required

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Price per night from

$319

Palm Bay Club - 303: By Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Staffed property, Car not required

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Price per night from

$341

Sun and Sea: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Staffed property, Car not required

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Price per night from

$284

Crescent Beach Villas - La Perlita: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Staffed property, Car not required

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Price per night from

$273

Ten35 Seaside - Island View: Residence 404

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, Car not required

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Price per night from

$547

Ten35 Seaside - Direct Gulf View: Residence 501

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, Car not required

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Price per night from

$946

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, Car not required, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$114

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, Car not required, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$742

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, Car not required

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Price per night from

$408

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, Car not required

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Price per night from

$239

Island Village Hideaway! Steps to Sand

Longboat Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 4 match: Staffed property, Golf course on site or within 15 min walk, Rental types, Car not required

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Price per night from

$192

2 of 4 match: Rental types, Car not required, Golf course on site or within 15 min walk, Staffed property

2 of 4 filters match

Price per night from

$283

Ten35 Seaside - Direct Gulf View: Residence 301

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, Car not required

2 of 4 filters match

Price per night from

$855

Jamaica Royale - Beachfront Tower: By Beachside Management

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, Car not required

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Price per night from

$376

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, Car not required

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Price per night from

$775

Gulf Holiday: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Staffed property, Car not required

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Price per night from

$170

Ten35 Seaside - South Water View: Residence 302

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, Car not required

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Price per night from

$604

Ten35 Seaside - Direct Gulf View: Residence 307

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, Car not required

2 of 4 filters match

Price per night from

$855

Ten35 Seaside - North Water View: Residence 410

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, Car not required

2 of 4 filters match

Price per night from

$627

Crescent Beach Villas - La Estrella: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Staffed property, Car not required

2 of 4 filters match

Price per night from

$273

Ten35 Seaside - Direct Gulf View: Residence 405

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Staffed property, Car not required

2 of 4 filters match

Price per night from

$855

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, Car not required

2 of 4 filters match

Price per night from

$547

BEACH RESIDENCES on Siesta, aka The Hyatt – 3 Bed/3 Bath Luxury Penthouse

Siesta Key hotel apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Staffed property, Car not required

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Price per night from

$513

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, Car not required

2 of 4 filters match

Price per night from

$558

Living the Dream - Starfish: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Staffed property, Car not required

2 of 4 filters match

Price per night from

$341

Ten35 Seaside - North Water View: Residence 310

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, Car not required

2 of 4 filters match

Price per night from

$627

Viewing 38 of 653
rentals in Longboat Key

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