Once Upon a Vacay

09/19/2026

🍂 October Magic Awaits at Once Upon A Vacay! 🎃

Windsor Hills Resort • Kissimmee, Florida
October is the perfect time for a magical getaway! ✨ Whether you're planning a family vacation, a Halloween adventure, or a fall escape, come enjoy everything Central Florida has to offer.

🎃 October is full of fun!

Mickey’s Not-So-Scary Halloween Party
Halloween fun at the theme parks
Epcot International Food & W**e Festival
Fall decorations, festive treats & seasonal events

🏡 Make yourself at home!

Our remodeled 3-bedroom condo at Windsor Hills Resort is the perfect place to relax after a day of adventure. With room for the whole family, you'll have space to unwind and make unforgettable memories.

📅 Thinking about an October getaway?

Now is the time to plan your stay! Check out our listing and find your dates for a little October magic.

✨ Book your stay at Once Upon A Vacay and make this October one to remember!

09/11/2026

09/10/2026

🏝️✨ NEW POOLSIDE CABANAS AT WINDSOR HILLS! ✨🏝️

Planning your next Orlando vacation? 🌴☀️ Windsor Hills has a NEW way to relax by the pool!

🏖️ POOLside CABANAS ARE COMING! 🏖️

Enjoy a shaded private space with family and friends while you take a break from the Florida sunshine. 💦☀️

✨ CABANA PRICING DEPENDS ON THE DATE:

🌴 NON-PEAK DATES
• Half-Day — $125
• Full-Day — $175

✨ PEAK DATES
• Half-Day — $175
• Full-Day — $250

📅 BOOKING OPENS FRIDAY, SEPTEMBER 11!

👉 Book your cabana directly through Windsor Hills:
🌴 Book Your Cabana Online⁠

⚠️ Prices depend on the date and are subject to change without notice. Please check Windsor Hills for current pricing and availability.

🏰✨ Once Upon A Vacay
Your Home Away From the Magic!

📍 Windsor Hills Resort • Kissimmee, FL

08/27/2026

🌴 NEW AT WINDSOR HILLS! 🌴

Something exciting is coming! 👀✨

New poolside cabanas are currently being added at Windsor Hills Resort! 🏖️☀️

Imagine relaxing in the shade between swims, taking a break from the Florida sunshine, and enjoying even more time outside with your family. 💦🌴

We can’t wait to see the finished cabanas — and we can’t wait for our guests to enjoy them! ❤️

🏡 Stay at Once Upon a Vacay
🏰 Minutes from Disney
🌴 Windsor Hills Resort
✨ More resort fun coming soon!

What do you think of the new cabanas? 👇

08/27/2026

✈️ Flying into Orlando for your next Disney vacation? 🏰✨

One of the best things about staying at Windsor Hills Resort is how convenient it is!

📍 Just a short drive from Orlando International Airport (MCO)
🚗 Easy access to Disney World & all the magic
🏡 A spacious 3-bedroom condo that sleeps up to 8
✨ The perfect place to relax after a busy day in the parks

Whether you’re coming for the rides, the food, the sunshine, or all of it — your magical getaway starts here! 💙

📅 Now accepting bookings for 2026/2027!

Message me for availability and booking information. 🏰🌴

08/25/2026

🏡✨ STAYING AT ONCE UPON A VACAY? SAVE THIS POST! ✨🏡

Because sometimes the unexpected happens while you’re on vacation! 🩺❤️

If you or someone in your family needs medical care during your stay, it’s good to know there’s an urgent care just minutes from the condo.

📍 AFC Urgent Care Kissimmee
⏰ Open 7 days a week
🚗 Just minutes from Windsor Hills Resort
🩹 Walk-ins welcome
💙 Illnesses • Injuries • X-rays • Lab Testing & More

Hopefully you won’t need it—but having this information handy can give you one less thing to worry about while you’re enjoying your Disney vacation! ✨🏰

📌 Save this post for later & share it with anyone staying with you!

🏠 Once Upon A Vacay
✨ Your home away from home near Disney!
📍 Windsor Hills Resort | Kissimmee, FL

08/24/2026

✨🎃 FALL MAGIC IS WAITING AT DISNEY! 🎃✨

There’s nothing quite like a fall getaway to Walt Disney World! 🍂🏰 From Halloween fun and festive treats to EPCOT’s Food & W**e Festival and all the cozy fall vibes, there’s so much to experience this season. 🎃🍁

🏡 Make Once Upon A Vacay your home base!
📍 Windsor Hills Resort • Kissimmee, FL
✨ Just minutes from Walt Disney World
🛏️ Perfect for families looking for a comfortable place to relax after a magical day in the parks!

Whether you’re planning a quick fall escape or a full Disney vacation, now is the perfect time to start planning! 🧡

🎟️ Halloween
🍷 Food & W**e
🍂 Fall at Disney
🎃 Seasonal fun & entertainment
🏰 And plenty of Disney magic!

https://www.airbnb.com/h/onceuponavacay

**e

08/23/2026

✨ Stay at Windsor Hills and enjoy it all! 🏰🌴

Planning your next Disney vacation? Make Once Upon A Vacay your home away from home! 🏡✨

Our remodeled 3-bedroom, 2-bath condo comfortably sleeps up to 8 guests and is just minutes from Walt Disney World. Enjoy the space, comfort, and convenience of having a vacation home while enjoying everything Windsor Hills has to offer. ❤️

💦 And the best part? Resort amenities are FREE for our guests!

📅 Check availability & book your stay:
Once Upon A Vacay on Airbnb⁠

✨ More space. More fun. Minutes from the magic! ✨

08/21/2026

🏀🏓 SPORTS EQUIPMENT RENTALS ARE NOW AVAILABLE AT WINDSOR HILLS! 🎾🏐

Make the most of your stay and get outside, have some fun, and enjoy all that Windsor Hills has to offer! 🌴☀️

🎱 Billiards – 1 hour
🏓 Ping Pong – 1 hour
🏀🏐 Basketball & Volleyball – 3 hours
🎾🏌️ Tennis & Golf – 3 hours
🏓 Pickleball – 3 hours

💵 CASH ONLY
A refundable deposit is required and returned when the equipment is brought back on time and in good condition.

📍 Windsor Hills Resort
⏰ Equipment must be returned by the agreed-upon time. Late returns may result in loss of deposit.

Whether you’re cooling off by the pool or enjoying a little friendly competition, there’s something for everyone! ❤️

Play More. Relax More. Make Memories. ✨🌴

📲 Save this post for your next Windsor Hills stay!