Houses Longboat Key

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628 houses

Oceanfront home

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Rental types Sea view Staffed property

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Price per night from

$684

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Buttonwood 442

Gulf Gate Estates condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$290

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$229

Amazing Beachfront Condo, Siesta Key,

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$343

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$270

2 of 3 match: Rental types, Sea view, Staffed property

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$143

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$283

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$434

Zilli Ocean Front 201 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$296

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

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$899

“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 3 match: Rental types, Sea view, Staffed property

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Price per night from

$143

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$428

Zilli Ocean Front 202 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$307

Ten35 Seaside - Direct Gulf View: Residence 301

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$855

Ten35 Seaside - North Water View: Residence 506

Siesta Key condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$775

Ten35 Seaside - South Water View: Residence 302

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Sea view, Staffed property

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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 3 match: Rental types, Sea view, Staffed property

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Price per night from

$855

Ten35 Seaside - North Water View: Residence 410

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$627

Ten35 Seaside - Direct Gulf View: Residence 405

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$855

Ten35 Seaside - North Water View: Residence 310

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$627

Ten35 Seaside - Direct Gulf View: Residence 303

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$855

Ten35 Seaside - North Water View: Residence 606

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$775

Ten35 Seaside - South Water View: Residence 602

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$684

Ten35 Seaside - Direct Gulf View: Residence 501

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$946

Ten35 Seaside - South Water View: Residence 502

Siesta Key condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$752

Ten35 Seaside - Direct Gulf View: Residence 403

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$855

Beachfront Condo Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$451

4 Bedroom with Gulf View Siesta Key FL Beach Fun

Siesta Key apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Fantastic Location and Beautiful Accomodations” Our daughters and their families stayed here in February. The condo was everything we expected and more. It has a breathtaking view of the Gulf from the screened in lani which runs the width of the unit. The four bedrooms were perfect for our group of nine and the kitchen / dining area was well stocked with appliances , pots & pans , dishes , glassware , etc. Condo has easy access to heated pool and ample parking. Owner made the rental process smooth as silk , and we all felt right at home as soon as we had checked in. Right across street from world famous Siesta Beach. Would highly recommend.

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$512

Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 1 minutes

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$265

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$109

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$191

March 23-March 30, 2024 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Sea view, Staffed property

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Price per night from

$742

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Sea view, Rental types, Staffed property

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Price per night from

$343

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

2 of 3 match: Sea view, Rental types, Staffed property

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Price per night from

$2,281

Riverfront Tropical Paradise W/ Private Island-Newly Updated Listing

Braden River house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Sea view, Rental types, Staffed property

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Price per night from

$250

Doveplum 221 at Midnight Cove Siesta Key, FL.

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Sea view, Rental types, Staffed property

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Price per night from

$256

Chinaberry 924 at Midnight Cove Siesta Key, FL.

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Sea view, Rental types, Staffed property

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Price per night from

$171

Firethorn 830 at Midnight Cove Siesta Key

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Sea view, Rental types, Staffed property

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Price per night from

$142

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