Happy Days Orlando

12/02/2025

👀 🛝 🤩 🌴

11/01/2025

🍂 November might just be the best time to visit Orlando.
The summer heat fades, the crowds thin, and the parks — and pools — are pure magic. ☀️✨

At Happy Days Orlando, November days mean:
🌞 Warm sunshine and pool weather
🎢 Shorter lines at Disney and Universal
🎨 Fun fall activities right here at Windsor Island Resort

Whether it’s poolside games, crafts, or evening movie nights at the clubhouse — it’s the perfect time to unwind, explore, and make memories. 🌴💛

📅 Book your November or December stay now and enjoy FREE pool heat!
Available Dates:
Nov 5-15
Dec 13-26

10/12/2025

🏈 Game Day, Vacation Way 🏡🔥
Whether it’s cheering on your team or just soaking in the sunshine, Happy Days Orlando gives you the perfect spot to relax, grill, and enjoy every moment.

💦 FREE Pool Heat for October bookings
📺 Patio TV + grill
🍔 Backyard tailgate vibes

Fall Break dates are still open — grab your last-minute getaway now!

License #: DWE6316811

10/11/2025

✨ Last-minute Fall Break Escape ✨ AVAILABLE OCT. 15-24
🎃✨ Halloween Magic Awaits Just Minutes Away ✨🎃
Spooky season at Disney is pure magic — from Mickey’s Not-So-Scary Halloween Party to glowing pumpkins on Main Street. 🏰🍂

📍 Happy Days Orlando — your home base for the magic!
💦 FREE Pool Heat all October
☀️ Resort-style pool & lazy river
🚗 Just minutes from Disney
🎢 Perfect for families & groups

Book your fall getaway direct on our website for our best pricing and to save on Airbnb Fees: www.happydaysorlando.com

12/15/2024

Dec. 20-25 available due to a cancellation. DM me or book direct on our website and beat the core Christmas rush.

FREE POOL/SPA HEAT AND BBQ GRILL

www.happydaysorlando.com

🏠 Windsor Island Resort
🛏 6 bedrooms 9 beds, sleeps 12
🚽 4.5 bathrooms
🎮 game room 🦖 🎱
👙 Heated pool & spa
💦 water park with lazy river, slides, pool
👩‍🍳 kitchen with everything you need
🍹clubhouse (restaurant, poolside bar, cafe, FREE gameroom, water park , volleyball, basketball & putt putt golf)
🏰 8 miles to Disney World
🏝 1 hour to Tampa & Clearwater beach area

Check out our website to request your free instant quotes or DM me with any questions.

License #: DWE6316811

Happy Days Orlando

09/28/2024

Tell us your favorite in the comments! Is it the amazing Disney World 🏰... or the fantastic Universal Studios 🌎?

09/16/2024

Shopping trip, anyone? 🛍️ Visit Park Avenue for a lovely day of boutique shopping and local eats! Enjoy the scenic streets and gorgeous landscaping 🌷 between checking out shops!

09/12/2024

Here's a look at our lovely upstairs primary bath! Who doesn't love a private bathroom on a busy family trip? We know having space to yourself can be a lifesaver when traveling with a large group, but you don't have to stress with Happy Days Orlando!

08/28/2024

Calling all air hockey 🏒 fans! Windsor Island Resort has got it all! Become a high-speed motorcycle racer 🏍️ or a basketball star 🏀 with this spectacular arcade!

08/20/2024

🦖 JURASSIC GAME ROOM 🎮 or 🦸🏻‍♀️ MARVEL
MOVIE ROOM 🎥
Let us know what you're choosing in the comments below! Happy Days Orlando really has it all! Check out all our amazing themed rooms at happydaysorlando.com!

08/14/2024

From now until Halloween night, Disney World is setting off 🎃 spooky season 👻 with Mickey's Not-So-Scary Halloween Party. This bash is jam-packed with frights for the whole family! Happy Days Orlando is only 20 minutes away from the Halloween of a lifetime! ✨🧙🏽‍♀️🎃

🎃