Sweet Pineapple-Sarasota, FL

08/28/2026

🍍 Sweet Pineapple – Sarasota, FL
Looking for a clean, peaceful Sarasota getaway this fall, winter, or next year? Sweet Pineapple has open availability for November, December, and April through December 2027 — and it’s the perfect spot to relax, explore, and enjoy Florida sunshine! (30-day minimum required by county laws)

Guests love:
• A sparkling clean home with a beautiful pool and enclosed pool deck
• A quiet, safe neighborhood ideal for morning walks and evening swims
*Local Preserve only 3 blocks away
• Quick access to Pinecraft and Downtown Sarasota
• Only 7 miles to Siesta Key, Lido Beach, and Longboat Key
• Close to restaurants, Amish cooking, shopping, and all the best Sarasota attractions
*Dog friendly to responsible dog owners

Whether you’re planning a holiday escape, a spring retreat, or a long summer stay, Sweet Pineapple is ready to welcome you.

Book direct for best pricing:
https://www.gcvacationrentals.com/vacation-rentals/sweet-pineapple/

Gulf Coast Vacation Rentals: Sweet Pineapple in Sarasota Vacation Rentals. Gorgeous 2 BR / 2 BA Private Pool Home Near Siesta Key

08/28/2026

🍍 Sweet Pineapple – Sarasota, FL
Looking for a clean, peaceful Sarasota getaway this fall, winter, or next year? Sweet Pineapple has open availability for November, December, and April through December 2027 — and it’s the perfect spot to relax, explore, and enjoy Florida sunshine! (30-day minimum required by county laws)

Guests love:
• A sparkling clean home with a beautiful pool and enclosed pool deck
• A quiet, safe neighborhood ideal for morning walks and evening swims
*Local Preserve only 3 blocks away
• Quick access to Pinecraft and Downtown Sarasota
• Only 7 miles to Siesta Key, Lido Beach, and Longboat Key
• Close to restaurants, Amish cooking, shopping, and all the best Sarasota attractions
*Dog friendly to responsible dog owners

Whether you’re planning a holiday escape, a spring retreat, or a long summer stay, Sweet Pineapple is ready to welcome you.

Book direct for best pricing:
https://www.gcvacationrentals.com/vacation-rentals/sweet-pineapple/

08/20/2026

***Sweet Pineapple (Nov 1–Dec 19 Availability)***
Website: https://bit.ly/3U4Gwix
Escape to sunny Sarasota this holiday season at Sweet Pineapple, our bright and cozy vacation rental just minutes from the Gulf beaches.

We have openings from November 1 through December 19 — perfect for snowbirds, remote workers, or anyone wanting a warm Florida getaway.
30‑day minimum stay.

Enjoy peaceful mornings on the lanai, nearby beaches, walkable dining, and the relaxed coastal vibe Sarasota is known for.

Best price is always when you book direct through Gulf Coast Vacation Rentals. https://bit.ly/3U4Gwix
Your winter escape is waiting.

07/19/2026

🐾🌴 Sweet Pineapple is now DOG‑FRIENDLY! 🌴🐾
We’re so excited to welcome pups to stay with their responsible pet owners — because vacations are better with wagging tails and sandy paws! 🐕💦

And guess what? We’ve got a local gal right here in Tamaron who offers amazing pet care services! 💛

She's experienced, reliable, caring, and right here in the Tamaron Subdivision serving our community! 🌳🐾

We are on all the STR Channels- Airbnb, VRBO, Home Away, Booking.com, etc but the best price will be direct thru our property management company: https://www.gcvacationrentals.com/vacation-rentals/sweet-pineapple/

30 night minimum, contact us directly if you run into any problems or special situations.

04/07/2026

Hi Snowbirds! We host a monthly rental 2/2 sleeps 6, in Sarasota and love welcoming long‑term guests! It has a private pool, sunroom/great workspace, and is in a peaceful neighborhood close to everything- beaches, restaurants, and entertainment! If you want photos or availability, I’m happy to send them over. We are originally from the U.P. of Michigan and know how long those winters get! ~Deana

04/01/2026

🍍🤣 APRIL FOOLS’… but also NOT REALLY! 🤣🍍

We almost announced a brand‑new “30‑minute minimum stay” at Sweet Pineapple so people could swing by, cannonball into the pool, grab a selfie, and be home before their coffee cooled.

But apparently Sarasota, physics, and common sense all said:
“Yeah… no.”

So here’s the real update:
✨ Sweet Pineapple is now offering discounts on a 30‑DAY OR MORE stay! ✨

Perfect for:

❄️ Snowbirds who aren’t ready to fly north

🛠️ Locals living through renovations, insurance repairs, or contractor chaos

🌴 Anyone craving a month of sunshine, pool time, and peace

And the location? The Best!
We’re minutes from Shopping, downtown Sarasota, loads of entertainment, and......

🏖️ Siesta Key Beach

🏖️ Lido Beach

🏖️ Longboat Key

🥧 Less than a mile----Pinecraft Amish Mennonite Village — home of Yoder’s pie, Dutch‑Heritage comfort food, and the friendliest community vibes around!

If you know someone who needs a comfy, quiet, fully stocked home for 30+ days, please share — it truly helps small hosts like us. 💛

📍 Book direct & save:
https://www.gcvacationrentals.com/vacation-rentals/sweet-pineapple/

Gulf Coast Vacation Rentals: Sweet Pineapple in Sarasota Vacation Rentals. Gorgeous 2 BR / 2 BA Private Pool Home Near Siesta Key

03/31/2026

If you haven't gone bioluminescent kayaking in Florida, you're missing out! Experience the magic as the dark water lights up around you!

03/30/2026

🌴☀️ Snowbird Escape in Sunny Sarasota – “Sweet Pineapple” 🍍

Looking to trade snow boots for flip flops this winter? Welcome to Sweet Pineapple, your cozy Florida retreat in beautiful Sarasota!

✨ The Highlights:
• Bright, fully furnished 2BR/2BA home
• Peaceful neighborhood with a relaxing, tropical vibe
• Spacious lanai – perfect for morning coffee or sunset cocktails
• Fully equipped kitchen + comfortable living space
• Fast WiFi + in-unit laundry
• Private driveway & plenty of parking

📍 Location, Location, Location:
Just a short drive to world-famous beaches like Siesta Key, Lido Key and Longboat key, or jaunt down to Venice Beach to go shark tooth hunting! Plus easy access to shopping, dining, golf, and all that Sarasota has to offer.

🌞 Perfect for Snowbirds
Available for 30+ day stays (ideal for seasonal renters!)
Enjoy warm weather, sunshine, and a slower pace all winter long.

📅 Seasonal Availability:
Winter months are filling fast! Available year-round!

🔗 Direct Booking (Best Rates):
https://www.gcvacationrentals.com/vacation-rentals/sweet-pineapple/

💬 DM for pricing, availability, and more details. Your slice of sunshine is waiting!

🍍 Come relax, unwind, and make Sweet Pineapple your home away from home.

Gulf Coast Vacation Rentals: Sweet Pineapple in Sarasota Vacation Rentals. Gorgeous 2 BR / 2 BA Private Pool Home Near Siesta Key

03/30/2026

Beautiful Siesta Key!

Take advantage of fast, convenient beach equipment rentals during your next Siesta Beach day! Leave your bulky beach equipment at home while you sit back and relax. Rent beach chairs, umbrellas and more via the Boucher Brothers. Single items and combo packages are available daily from 9 AM to 5 PM, weather-permitting.

Learn more here: www.siestabeacheats.com/rentals

03/18/2026

🍍 Your Month-Long SARASOTA ESCAPE Awaits at Sweet Pineapple! 🍍

Ready to settle into sunshine for 30 days or more? Sweet Pineapple offers the perfect extended-stay retreat — spacious, private, and close to everything Sarasota is known for.
☀️ Private heated pool with a 45 ft Pineapple 🍍Garden
🌴 Quiet, friendly neighborhood
🏡 Bright, open layout that sleeps 6
⛱️ Minutes to Siesta Key, Lido, and Longboat beaches
🔥 Sunroom, firepit, garage, basketball hoop — plenty of space to unwind

Whether you're escaping winter, working remotely, or just craving a long, peaceful getaway, Sweet Pineapple feels like home from the moment you arrive.

📅 Best rates are always direct: 👉 https://www.gcvacationrentals.com/vacation-rentals/sweet-pineapple/ (Also listed on Airbnb, VRBO, Booking, Marriott & all major vacation rental channels if you prefer to book there)


T/W/TH and Sunday Evening