Happy Days Orlando

05/24/2026

The kids finally crashed.
The pool is still warm.
And for the first time all day… it’s quiet. ☀️🌴

One of our favorite things about staying at a vacation home instead of a hotel is getting space to actually relax after the parks.

Slow mornings.
Pool afternoons.
Sunset swims.
Late night movies outside.

That’s the kind of vacation we wanted Happy Days Orlando to feel like.

www.HappyDaysOrlando.com

License # DWE6316811

05/24/2026

The kids finally crashed.
The pool is still warm.
And for the first time all day… it’s quiet. ☀️🌴

One of our favorite things about staying at a vacation home instead of a hotel is getting space to actually relax after the parks.

Slow mornings.
Pool afternoons.
Sunset swims.
Late night movies outside.

That’s the kind of vacation we wanted Happy Days Orlando to feel like.

www.HappyDaysOrlando.com

License # DWE6316811

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!