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 Garden Kettle Staffed property

All filters match

Price per night from

$149

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Rental types Garden Kettle Staffed property

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Price per night from

$344

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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, Garden, Kettle, Staffed property

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Price per night from

$184

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, Garden, Kettle, Staffed property

2 of 4 filters match

Price per night from

$194

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Rental types, Garden, Kettle, Staffed property

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Price per night from

$229

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Rental types, Garden, Kettle, Staffed property

2 of 4 filters match

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, Garden, Kettle, Staffed property

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Price per night from

$482

2 of 4 match: Rental types, Garden, Kettle, Staffed property

2 of 4 filters match

Price per night from

$144

“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, Garden, Kettle, Staffed property

2 of 4 filters match

Price per night from

$144

2 of 4 match: Rental types, Garden, Kettle, Staffed property

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Price per night from

$284

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, Garden, Kettle, Staffed property

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Price per night from

$337

Zilli Tower 503

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

2 of 4 match: Rental types, Garden, Kettle, Staffed property

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Price per night from

$343

Zilli Ocean Front 201 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

2 of 4 match: Rental types, Garden, Kettle, Staffed property

2 of 4 filters match

Price per night from

$297

Zilli Ocean Front 202 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

2 of 4 match: Rental types, Garden, Kettle, Staffed property

2 of 4 filters match

Price per night from

$308

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, Garden, Kettle, Staffed property

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Price per night from

$903

+++ 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, Garden, Kettle, Staffed property

2 of 4 filters match

Price per night from

$178

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Rental types, Garden, Kettle, Staffed property

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Price per night from

$430

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, Garden, Kettle, Staffed property

2 of 4 filters match

Price per night from

$114

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 4 match: Rental types, Garden, Kettle, Staffed property

1 of 4 filters match

Price per night from

$192

Hidden gem close to everything

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 14 minutes

1 of 4 match: Kettle, Garden, Staffed property, Rental types

1 of 4 filters match

Price per night from

$217

1 of 4 match: Kettle, Garden, Staffed property, Rental types

1 of 4 filters match

Price per night from

$125

Modern Home close to Beach & Downtown

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 4 match: Kettle, Garden, Staffed property, Rental types

1 of 4 filters match

Price per night from

$229

Beautiful Sunkst Cottage Bradenton Beach - AMI-Tropical Setting - Heated Pool

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

2 of 4 match: Garden, Staffed property, Rental types, Kettle

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Price per night from

$516

ISLAND TOWNHOUSE - 200 Steps to the BEACH

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 43 minutes

2 of 4 match: Garden, Staffed property, Rental types, Kettle

2 of 4 filters match

Price per night from

$206

Charming Lido Key Beach House 5 min Walk to Beach!

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 4 match: Garden, Staffed property, Rental types, Kettle

2 of 4 filters match

Price per night from

$409

Stunning 2,550 Sq.ft House, FL

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Garden, Staffed property, Rental types, Kettle

2 of 4 filters match

Price per night from

$286

2 of 4 match: Garden, Staffed property, Rental types, Kettle

2 of 4 filters match

Price per night from

$310

NEAR IMG ACADEMY AND SIESTA KEY BEACH PARADISE

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 9 minutes

2 of 4 match: Garden, Staffed property, Rental types, Kettle

2 of 4 filters match

Price per night from

$430

Coastal Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Garden, Staffed property, Rental types, Kettle

2 of 4 filters match

Price per night from

$172

Flamingo Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Garden, Staffed property, Rental types, Kettle

2 of 4 filters match

Price per night from

$172

Sea Shell Cottage

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Garden, Staffed property, Rental types, Kettle

2 of 4 filters match

Price per night from

$172

The Corner Retreat

Bradenton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Garden, Staffed property, Rental types, Kettle

2 of 4 filters match

Price per night from

$182

Five star Downtown Sarasota tropical garden Cottage

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Paradise Found in Downtown Sarasota” Absolutely charming, fully redone/ upgraded bungalow close to everything Sarasota has to offer. This was the third year running my wife & I have stayed at the wonderful home located minutes from Sarasota's best beaches, restaurants & shopping. We fully intend to return again next year! The two bedroom home is in pristine condition. Beautifully decorated, lovely hardwood flooring throughout with a fully stocked (appliances, crockery, pots/pans, cutlery, etc...) kitchen & renovated bathroom. Everything you need is provided, just arrive & settle-in. A huge projection screen in the living room, should you want to have an at-home movie night (rental Dvd's a 5-minute walk away @ Publix). There's also a regular flat-screen TV in the living room, as well as a wall-mounted TV in the bedroom. The backyard is, personally, my favourite part of the home. A screen-in lanai to eat in & a beautifully manicured backyard to relax in under the tiki hut or under the palm trees. There are a few seating areas throughout the backyard. Find the space you like the best, sit-back & relax with a cool cocktail- very civilized & very beautiful. You'll feel like you're in the Caribbean, not Florida in this backyard. Maureen & Pat, your hosts who, very conveniently, live right next door have provided everything you need, including all the beach chairs, umbrellas, beach towels, etc...to take along with you to Sarasota's beautiful beaches. Maureen has also provided tons of literature about the area in the house- restaurant menus, local mags, maps- everything. Maureen & Pat are always happy to suggest restaurants, beaches, shopping, golf, etc. They know Sarasota well, are friendly & happy to help in any way they can to ensure you have a wonderful stay. My wife & I can honestly say we love this property, have encountered no negatives about the place in three years of week-long stays & look-forward to our time there each year. We recommend this lovely home to everyone.

2 of 4 match: Garden, Staffed property, Rental types, Kettle

2 of 4 filters match

Price per night from

$189

Beachfront Paradise w/ Private Beach, Dogs Stay Free, Beach in Backyard

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Garden, Staffed property, Rental types, Kettle

2 of 4 filters match

Price per night from

$630

Stunning & Bright Sarasota Home

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Garden, Staffed property, Rental types, Kettle

2 of 4 filters match

Price per night from

$395

Heated pool home near Siesta Key

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Garden, Staffed property, Rental types, Kettle

2 of 4 filters match

Price per night from

$263

Responds fast! avg. 0 minutes

2 of 4 match: Garden, Staffed property, Rental types, Kettle

2 of 4 filters match

Price per night from

$229

2 of 4 match: Garden, Staffed property, Rental types, Kettle

2 of 4 filters match

Price per night from

$344

Viewing 38 of 809
rentals in Longboat Key

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