Is Windsor Hills Worth It? Why This Resort Near Disney Stands Out
Planning a trip to Disney World and searching for a place to stay nearby? You’ve probably come across Windsor Hills Resort in Kissimmee. It’s one of the most talked-about gated communities near Orlando’s theme parks. But is Windsor Hills worth it?
Short answer: Yes. And here’s why.
In this blog, we’ll break down what makes Windsor Hills a favorite for families, couples, and groups looking for short-term rentals near Disney. We’ll also help you decide if it’s the right fit for your trip, with insights from a local property manager who knows the area inside and out.
What Is Windsor Hills Resort?
Windsor Hills is a gated vacation rental community just 2 miles from Walt Disney World. Located in Kissimmee, Florida, it’s one of the closest non-Disney accommodations you can find. The neighborhood is filled with townhomes, condos, and large vacation homes, many of which feature private pools.
It’s not a hotel. It’s not a theme park resort. However, it offers space, privacy, and perks that make it a solid choice for travelers seeking something more flexible than a hotel room.
Why Windsor Hills Keeps Popping Up in Your Search
If you’re in the early planning stage and searching for:
- “Best places to stay near Disney World”
- “Short-term rentals near Disney parks”
- “Family vacation rentals in Kissimmee with pool”
Windsor Hills shows up over and over again — and for good reason.
Location:
Just 10 minutes from the Magic Kingdom parking lot, it’s one of the closest gated vacation communities to Walt Disney World.
Security:
24/7 guarded gate entry with resort staff on-site. That means peace of mind while you’re out enjoying the parks.
Variety of Properties:
Choose from affordable 2-bedroom condos to luxury 6-bedroom villas. Many come with private pools, game rooms, and themed kids’ bedrooms.
Resort Amenities:
You’ll have access to:
- Lagoon-style pool with zero-entry
- Kids’ splash pad and waterslide
- Clubhouse with arcade, movie theater, and shop
- Fitness center, tennis, and basketball courts
Many vacationers say it feels like a mini-resort, just without the crowds or price tag of a hotel.
Comparing Options? Here’s What to Know
If you’re weighing Windsor Hills against other resorts or hotels in the Orlando area, consider these frequently asked questions:
How Close Is Windsor Hills to Disney World?
It’s just 2 miles away. On a good day, you’ll be inside the Disney gates in under 15 minutes. That’s even closer than some official Disney hotels.
Is It Family Friendly?
Absolutely. With splash pads, playgrounds, a game room, and kid-focused amenities, it’s built for families. Most rentals include full kitchens, laundry rooms, and multiple bedrooms — features that make life easier when traveling with little ones.
What’s Nearby?
Within a 10-minute drive, you’ll find:
- Publix, Walmart, and Target for groceries
- Dozens of restaurants like Ford’s Garage, Flippers Pizzeria, and Island Grove Wine Company
- Medical facilities and gas stations
You’re also near Celebration, Sunset Walk, and Old Town, perfect for casual strolls or low-key evenings.
Is It Budget Friendly?
Often, yes. For the price of two hotel rooms, you could rent a 3- to 5-bedroom Windsor Hills vacation home. You also save money by eating in and using the washer/dryer rather than doing laundry services.
Ready to Book? Here’s How to Choose the Right Rental
Not all Windsor Hills properties are created equal. Some are older or managed from afar. Others are professionally maintained, modernized, and ready for guests, like Chillax Inn.
When you book Chillax Inn at Windsor Hills, you get:
- A private screened-in pool
- 3 bedrooms and 2 bathrooms, ideal for families or small groups
- High-speed Wi-Fi and smart TVs for streaming
- A fully stocked kitchen for home-cooked meals
- Free parking and laundry on-site
- Direct access to all resort amenities
Want to skip third-party booking fees? You can book direct at chillaxinn.com for the best rates and faster support from local hosts.
What Sets Windsor Hills Apart From Other Vacation Communities?
You might also be comparing Windsor Hills to other popular Orlando vacation neighborhoods like:
- Storey Lake– newer and stylish, but farther from Disney and often more expensive
- Encore Resort– comes with a waterpark, but usually geared toward large groups with a higher price tag
- Emerald Island– similar layout and feel, but slightly older and farther out
Windsor Hills is known for being the best mix of value, amenities, and proximity to the theme parks. For travelers searching terms like:
- “vacation rental near Disney with private pool”
- “resort-style short-term rental in Orlando”
- “best gated communities near Disney World”
Windsor Hills is consistently a top result for a reason.
Day-to-Day Life at Windsor Hills
Want a peek at what staying here is really like?
Wake up and enjoy coffee on your private patio. Take a walk through the landscaped paths or get a morning workout in the gym. The kids head straight to the splash pad while you prep lunch in your own kitchen. Later, head out to Disney Springs or enjoy dinner at a restaurant just five minutes away.
It’s vacation on your terms. No shuttle schedules. No elevator waits. No crowded lobbies.
Who Is Windsor Hills For?
Windsor Hills is perfect for:
- Families with young kids
- Multi-gen trips with grandparents
- Friend groups going to Universal and Disney
- Snowbirds escaping winter for a month
- Remote workers looking for extended stays with great amenities
With flexible short-term rental options and all the comforts of home, you get more space, more privacy, and a more relaxed trip overall.
So, Is Windsor Hills Worth It?
Yes. If you’re looking for a quiet, secure, and well-located community near the Disney parks, Windsor Hills checks every box. It has the space you need, the amenities you’ll use, and the location that makes your Orlando stay easier.
And if you want to book one of the best vacation homes in Windsor Hills? Chillax Inn is ready for your next getaway.
Check availability and book direct today!
Make your Disney trip more comfortable, more affordable, and more memorable, all from a short-term rental that feels like home.
