Houses Longboat Key

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827 houses

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Rental types Kettle Staffed property Pets allowed

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Price per night from

$149

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Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 46 minutes

3 of 4 match: Rental types, Kettle, Staffed property, Pets allowed

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Price per night from

$194

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Rental types, Kettle, 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

3 of 4 match: Rental types, Kettle, Staffed property, Pets allowed

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Price per night from

$482

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

3 of 4 match: Kettle, Rental types, Staffed property, Pets allowed

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Price per night from

$2,289

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, Kettle, Staffed property, Pets allowed

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Price per night from

$115

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, Kettle, Staffed property, Pets allowed

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Price per night from

$448

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Pets allowed, Rental types, Kettle, Staffed property

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Price per night from

$345

Banana Cabana: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Kettle, Staffed property, Pets allowed

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Price per night from

$240

Living the Dream - Pink Flamingo: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Rental types, Kettle, Staffed property, Pets allowed

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Price per night from

$320

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Rental types, Pets allowed, Kettle, Staffed property

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Price per night from

$230

Downtown Sarasota Historic Burns Court Adorable Bungalow

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Rental types, Kettle, Pets allowed

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Price per night from

$295

Living the Dream - Starfish: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Rental types, Kettle, Staffed property, Pets allowed

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Price per night from

$343

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Rental types, Pets allowed, Kettle, Staffed property

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Price per night from

$431

“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, Pets allowed, Kettle, Staffed property

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Price per night from

$144

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, Pets allowed, Kettle, Staffed property

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Price per night from

$338

Gulf and Bay Club 3bdrm “E” Luxury END CORNER Unit - RIGHT ON BEACH

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 4 match: Rental types, Pets allowed, Kettle, Staffed property

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Price per night from

$904

Zilli Ocean Front 201 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

2 of 4 match: Rental types, Pets allowed, Kettle, Staffed property

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Price per night from

$298

Zilli Ocean Front 202 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

2 of 4 match: Rental types, Pets allowed, Kettle, Staffed property

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Price per night from

$309

2 of 4 match: Rental types, Pets allowed, Kettle, Staffed property

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Price per night from

$285

Zilli Tower 503

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

2 of 4 match: Rental types, Pets allowed, Kettle, Staffed property

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Price per night from

$343

2 of 4 match: Rental types, Pets allowed, Kettle, Staffed property

2 of 4 filters match

Price per night from

$144

Lido Beach Villa, 1.2k sf, 1 block to the beach

Lido Key villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Rental types, Pets allowed, Kettle, Staffed property

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Price per night from

$184

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, Kettle, Staffed property

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Price per night from

$114

+++ 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, Kettle, Staffed property

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Price per night from

$178

Remodeled Exquisite Home. 10 min from the Beaches of Anna Maria Island. 7min IMG

South Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

3 of 4 match: Staffed property, Rental types, Kettle, Pets allowed

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Price per night from

$343

3 of 4 match: Staffed property, Rental types, Kettle, Pets allowed

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Price per night from

$108

3 of 4 match: Staffed property, Rental types, Kettle, Pets allowed

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Price per night from

$183

Flip Flops Forever

Holmes Beach house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

3 of 4 match: Staffed property, Rental types, Kettle, Pets allowed

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Price per night from

$419

Jacaranda Artist Retreat

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Rental types, Kettle, Pets allowed

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Price per night from

$218

Luxury Modern Oasis in Heart of Sarasota

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Staffed property, Rental types, Kettle, Pets allowed

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Price per night from

$1,032

From Dusk 'Til Dune

Anna Maria house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Rental types, Kettle, Pets allowed

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Price per night from

$742

On The Rocks

Bradenton Beach house

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 18

3 of 4 match: Staffed property, Rental types, Kettle, Pets allowed

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Price per night from

$953

Anna Maria Beach House

Anna Maria house

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Rental types, Kettle, Pets allowed

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Price per night from

$662

Tripletail

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Rental types, Kettle, Pets allowed

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Price per night from

$1,718

New Rental Sleek Modern Private Home, WiFi, Lanai

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 4 minutes

3 of 4 match: Staffed property, Rental types, Kettle, Pets allowed

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Price per night from

$287

Winding Waves

Anna Maria house

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Rental types, Kettle, Pets allowed

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Price per night from

$1,060

Rum Dog

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Rental types, Kettle, Pets allowed

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Price per night from

$173

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rentals in Longboat Key

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