Houses Longboat Key

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966 houses

Chinaberry 924 at Midnight Cove Siesta Key, FL.

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$171

Firethorn 830 at Midnight Cove Siesta Key

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$142

Doveplum 221 at Midnight Cove Siesta Key, FL.

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$256

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$2,295

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$149

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$345

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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

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Price per night from

$194

Tiny House Siesta - Sand Dollar – A private master loft and open living space

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$448

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

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$194

Sarasota Waterfront and Marina Community with Tikki Bar and Grill

North Sarasota condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$103

Buttonwood 442

Gulf Gate Estates condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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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

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Price per night from

$230

Palm Bay Club - 343: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$286

Banana Cabana: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$240

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

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$484

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$235

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$272

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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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!!

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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

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Price per night from

$338

Runaway Bay - Bradenton Beach - Bay View Unit 193

Anna Maria Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Home away from home” This place is an incredible value. It's spacious and comfortable, and we felt right at home. Sarasota Bay is just steps from the back patio, and it's so lovely to sit outside and watch water--so many fish, dolphins, and birds right there. Everything was in good working order and clean upon our arrival. The beach is a quick walk across the street from the complex, and we spent a lot of time at the heated pool. We would love to rent this unit again! PERFECT LOCATION.

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$209

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$437

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

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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$905

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

Lido Key villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$184

Zilli Ocean Front 201 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$298

+++ Clean & Bright +++ Minutes to Anna Maria Island

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

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Price per night from

$178

Zilli Ocean Front 202 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$309

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Price per night from

$285

Zilli Tower 503

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$344

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

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Price per night from

$114

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Price per night from

$144

Private Beach Access - Home away from Home - 2 BR 2 BA - Furnished Condo

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$178

Sun and Sea: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$286

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

Siesta Key hotel apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$516

Gulf Holiday: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$171

Ten35 Seaside - South Water View: Residence 302

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$607

Living the Dream - Pink Flamingo: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$321

Ten35 Seaside - Direct Gulf View: Residence 307

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$860

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rentals in Longboat Key

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