Houses Longboat Key

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895 houses

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Rental types Freezer Staffed property 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

3 of 4 match: Rental types, Walking trips, Freezer, Staffed property

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Price per night from

$430

3 of 4 match: Rental types, Walking trips, Freezer, Staffed property

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Price per night from

$284

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, Walking trips, Freezer, Staffed property

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Price per night from

$114

Responds fast! avg. 12 minutes

3 of 4 match: Rental types, Walking trips, Freezer, Staffed property

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Price per night from

$144

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

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Rental types, Walking trips, Freezer

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Price per night from

$344

“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, Freezer, Walking trips, Staffed property

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Price per night from

$144

2 of 4 match: Rental types, Freezer, Walking trips, Staffed property

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Price per night from

$144

3 of 4 match: Staffed property, Rental types, Walking trips, Freezer

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Price per night from

$297

The Pink Riverhouse-

Ellenton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Rental types, Walking trips, Freezer

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Price per night from

$693

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Freezer, Walking trips, Staffed property

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Price per night from

$271

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, Walking trips, Freezer

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Price per night from

$288

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Rental types, Walking trips, Freezer

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Price per night from

$1,260

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

3 of 4 match: Walking trips, Rental types, Freezer, Staffed property

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Price per night from

$2,298

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Walking trips, Rental types, Freezer, Staffed property

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Price per night from

$344

2 of 4 match: Rental types, Staffed property, Walking trips, Freezer

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Price per night from

$139

🏝Paradise on the Sarasota Bay, Close to Gulf Beaches🏝 (Sarasota)

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Rental types, Walking trips, Freezer, Staffed property

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Price per night from

$195

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 46 minutes

2 of 4 match: Rental types, Walking trips, Freezer, Staffed property

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Price per night from

$194

Buttonwood 442

Gulf Gate Estates condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Walking trips, Freezer, Staffed property

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Price per night from

$290

2 of 4 match: Rental types, Staffed property, Walking trips, Freezer

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Price per night from

$138

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.

2 of 4 match: Rental types, Staffed property, Walking trips, Freezer

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Price per night from

$509

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

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Rental types, Walking trips, Freezer, Staffed property

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Price per night from

$482

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Rental types, Walking trips, Freezer, Staffed property

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Price per night from

$234

Banana Cabana: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Walking trips, Freezer, Staffed property

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Price per night from

$240

Palm Bay Club - 343: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Walking trips, Freezer, Staffed property

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Price per night from

$286

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Rental types, Walking trips, Freezer, Staffed property

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Price per night from

$229

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: Freezer, Staffed property, Rental types, Walking trips

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Price per night from

$252

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: Freezer, Staffed property, Rental types, Walking trips

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Price per night from

$227

Close to Siesta key with hot tub, fire pit and butterfly garden

Gulf Gate Estates guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Rental types, Staffed property, Walking trips, Freezer

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Price per night from

$193

Ideal Retreat next to USA's #1 Beach—Siesta Key

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 4 match: Rental types, Staffed property, Walking trips, Freezer

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Price per night from

$161

3BR/4BA TOWNHOUSE - POOL VIEW PARADISE - PRIVATE BEACH ACCESS

Siesta Key townhouse

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 38 minutes

2 of 4 match: Rental types, Staffed property, Walking trips, Freezer

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Price per night from

$430

Ten35 Seaside - Island View: Residence 308

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Walking trips, Freezer, Staffed property

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Price per night from

$551

Ten35 Seaside - South Water View: Residence 302

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Walking trips, Freezer, Staffed property

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Price per night from

$608

Ten35 Seaside - Direct Gulf View: Residence 301

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Walking trips, Freezer, Staffed property

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Price per night from

$861

Ten35 Seaside - North Water View: Residence 410

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Walking trips, Freezer, Staffed property

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Price per night from

$631

Ten35 Seaside - Direct Gulf View: Residence 303

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Walking trips, Freezer, Staffed property

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Price per night from

$861

Ten35 Seaside - Island View: Residence 404

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

2 of 4 match: Rental types, Walking trips, Freezer, Staffed property

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Price per night from

$551

Ten35 Seaside - Island View: Residence 406

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Walking trips, Freezer, Staffed property

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Price per night from

$562

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rentals in Longboat Key

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