Vacation Rentals & Barns in Pinecraft

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306 barns

Oceanfront home w/sunset views of Sarasota Bay

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$629

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

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$267

Walk to Crescent Beach, Wifi, Bay Views From Lanai, Heated Pool, YTube TV, On T

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 4 minutes

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$139

Across the street from SK Beach, New Renovations!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$204

SK Beach Across the Street, WiFi, Overlooks Pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

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$131

Walk to Beaches, Bay Complex, Heated Pool,1st Flr

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$138

Last Minute Availability. Private Beach Access, Pool, Amenities, Dock View

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Beautiful condo” Great location with beach access and walking access to great restaurants. Only downside it was listed as 2 bathrooms when there were only 1 and 1/2

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$179

New Owners & Superbly Renovated, Walk to Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$161

Holiday House 1

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$91

Mid Century Modern Canal Home, Pool, King Master

Siesta Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

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$303

Walk to Siesta Beach, Heated Pool w/BBQ, Parking

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$133

Sea Club II

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$166

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$234

Beautifully Renovated & Modern in Harbor Towers

Siesta Key apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 4 minutes

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$206

Crescent Beach resort, Heated Pool, Jacuzzi, Tennis, Barbeques

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$315

Siesta Heron 1 / Antigua

Gulf Gate Branch condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$91

LuLu Kemp Ridley, Walk to Beach, Heated Pool, BBQ

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$213

Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.

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$190

Beachfront, Private Beach, Full Ocean Views, Pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$263

Coastal Reflections

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$103

Responds fast! avg. 4 minutes

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$163

LuLu's Leatherback Walk to Beach/Village, Pool/BBQ

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$225

Heated pool home near Siesta Key

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$263

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.

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$115

Little Palms Villa. A lakeside home with style.

Bradenton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Excellent” Our stay at 4638 Runabout way was amazing. We loved that the house was very nice, spacious, and clean for my family and I. We loved swimming in the pool everyday. The service was excellent all around. We would definitely stay there again.

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$195

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 57 minutes

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$194

Water Views Overlooking a Small Private Marina

Sarasota apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 4 minutes

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$197

Walk to Beach, Fishing Pier, Tennis, W/D in-Unit

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 4 minutes

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$138

Beach Across the Street, Partial Gulf Views, Pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$172

Luxury Village Townhouse w/ Gulf and Beach Views

Siesta Key townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“A wonderful home in an equally wonderful location.” The home provides a truly enjoyable family situation. The quality of the furnishings is very nice, the living space is very well maintained and clean and my interaction with the owner was always timely and courteous. My wife and I shared the home with our 14 year old granddaughter during our stay and the quiet enjoyment of the pool and the easy 1-2 minute walk to the Gulf of Mexico and the 5 minute walk to the heart of Siesta Key Village made the location hard to beat. Except for our day trips no car was needed. This is our second stay in the home and we will look to reserving it for our next visit. There were absolutely no disappointments only wonderful experiences.

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$659

~ SUPER SPECIAL from $99/night ~ OCEAN FRONT DLX STUDIO

Longboat Key studio

  • Studio
  • 1 bathroom
  • sleeps 3

“Nice Beachfront Location” We stayed there in late June and found it very suitable for our needs. The beach was very accessible. View was awesome. The unit was clean and comfortable for 2 adults.

Responds fast! avg. 1 hour 56 minutes

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$194

Luxurious 2 BR Condo-Short Walk to Siesta Beach/1 Small Dog (25 lbs Max) Allowed

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“a fine 2 weeks in Siesta” charming property, that was comfortable for four. The unit was very clean and fresh upon arrival. The neighbours were friendly and the overall property well kept. Siesta Key is a quiet community with usual shopping amenities over the causeway. This property was a brief 10 minute walk to the beach. Would we stay again, yes.

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$166

Luxury Sarasota Golf Home

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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$369

LuLu’s Green in the Heart of Siesta Key Village

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 4 minutes

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$213

Jamaica Royale #104! Completely renovated, Gulf side, beautiful 2b/2b Condo!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$338

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.

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$189

Lakefront Oasis 3 Bdrm House with Heated Pool minutes from village and beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$689

Charming Lido Key Beach House 5 min Walk to Beach!

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$410

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