Windsor Hills Vacation Rentals: What I Wish Every First-Time Guest Knew
After more than five years of hosting families at Windsor Hills Resort, I’ve learned that the questions guests ask before booking are often very different from the questions they ask once they arrive.
How far is Disney really?
Do you need a car?
What is the clubhouse like?
Is the pool actually private?
Do you have to pay resort fees?
And perhaps most importantly, how do you choose the right Windsor Hills vacation rental for your family?
We’ve hosted many wonderful guests at Windsor Hills over the years, and in 2026 we added a second home to our little corner of the resort.
So whether you’re considering Windsor Hills for your first Disney vacation or you’ve stayed here before, here are some of the things I think are actually worth knowing before you book.
What is Windsor Hills Resort?
If you’re searching for Windsor Hills vacation rentals near Disney World, you’ll quickly discover that Windsor Hills Resort is one of the most popular vacation-home communities in the Kissimmee area.
It’s a gated resort community located just off Highway 192, extremely close to Walt Disney World.
But Windsor Hills isn't a hotel.
You’re staying in an actual vacation home.
Depending on the home you choose, that can mean multiple bedrooms and bathrooms, a full kitchen, a living room, dining space, your own private pool and much more room to spread out than you would typically have in a hotel room.
For families, that can make a huge difference.
Instead of everyone sharing one hotel room, the kids can have their own bedrooms, adults can have some privacy, and you can come back from a long day at the parks and actually relax.
And yes, you can still be at Disney incredibly quickly.
How close is Windsor Hills to Disney World?
You’ll often see Windsor Hills vacation homes advertised as being 2 miles from Disney World.
That sounds almost too good to be true, but Windsor Hills really is that close to Disney property.
Of course, there’s an important distinction between being two miles from Disney property and being two miles from the front gate of Magic Kingdom.
Walt Disney World is enormous.
Your actual drive time depends on which park you're visiting, traffic, and exactly where you're going once you enter Disney property.
From Windsor Hills, though, you're starting from a very convenient location. That's one of the biggest reasons we chose to buy here in the first place.
For our guests, being close enough that you can head back to the house for an afternoon swim, a break, or a quick lunch can make a Disney day feel much less exhausting.
Do you need a car when staying at Windsor Hills?
This is one of those questions where the answer is: not necessarily.
We’ve had many guests stay with us without renting a car, and for some families, skipping the rental car can save a surprising amount of money.
Because Windsor Hills is so close to Disney World, Uber and other rideshare services can be a really convenient option, particularly for guests who are planning to spend most of their vacation at the Disney parks.
You can also have groceries delivered directly to the house, so you don't necessarily need a car just to stock the kitchen.
Of course, having a car can still be convenient if you're planning to visit Universal, explore further afield, go shopping frequently or simply prefer having your own transportation.
But I wouldn't assume you need one.
For a family spending most of their time at Disney, staying in a Windsor Hills vacation rental and using rideshare when you need it can be a very practical—and potentially much less expensive—way to do Orlando.
And that's another advantage of Windsor Hills' location. You're close enough to Disney that you have choices.
Yes, the private pool really is private
This is one of the things I think families sometimes don't fully understand when comparing Windsor Hills vacation rentals with private pools.
Many of the homes have their own screened-in private pool.
That means you aren't sharing it with everyone staying at the resort.
You can come back from the parks, change into your swimsuit and let the kids have some pool time without packing everyone up and heading to another resort pool.
For many families, especially those travelling with younger children, the private pool ends up being just as important as the proximity to Disney.
There is also a large resort pool and clubhouse, so you get both options.
One thing worth knowing when you're comparing homes is that private pools vary from house to house. Look carefully at the listing and don't assume every home has exactly the same pool setup.
If pool time is an important part of your vacation, it's also worth checking whether pool heat is available and what the additional cost is.
The Windsor Hills clubhouse is a big part of the resort experience
Windsor Hills isn't simply a neighbourhood full of rental houses.
The resort has a clubhouse and resort amenities that give you somewhere to go when you want a change of scenery.
The main pool area includes a large resort pool and waterslide, along with other amenities around the clubhouse.
One thing I always tell our guests is that the clubhouse isn't necessarily something you'll use every single day.
And that's okay.
Some days you'll spend the entire day at Disney.
Other days you may never leave your private pool.
That's one of the things I love about staying in a vacation home—you aren't locked into one way of vacationing.
Just remember that Windsor Hills is a resort community, so there are resort rules to follow. For example, guests using the clubhouse amenities need the appropriate resort wristbands.
Not all Windsor Hills vacation rentals are the same
This is probably the biggest piece of advice I can give someone booking their first Windsor Hills vacation rental.
Don't choose a home based solely on the photos or the nightly price.
There are a lot of homes in the community, and they can be very different.
When comparing Windsor Hills rentals, look at:
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The number of bedrooms and bathrooms
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Whether the pool is private
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Whether pool heat is available
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How close the home is to the clubhouse
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Whether there are rear neighbours
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The home's recent reviews
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How the home is maintained
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The quality of the beds and furniture
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What is actually included
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Cleaning and other fees
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Whether you're dealing directly with the owner or a management company
And don't be afraid to ask questions.
A good owner should be happy to tell you exactly what you're booking.
Why we have two Windsor Hills vacation homes
We originally purchased Belle's with our own family in mind.
It's a three-bedroom, three-bathroom townhome, and over the years it became something we were proud to share with other families visiting Orlando.
After hosting for several years, we eventually bought a second home in Windsor Hills: Motunui Villa.
Motunui is a five-bedroom, five-bathroom home that sleeps up to 11 guests, making it a great option for larger families and groups who want plenty of room to spread out.
The two homes are different, but our approach to both is the same.
We want guests to walk through the door and feel like the home has been prepared for an actual family vacation—not simply turned over for the next booking.
That means paying attention to the little things.
Comfortable beds.
A well-equipped kitchen.
Clean, well-maintained spaces.
Things for the kids to do.
A pool that's ready to be enjoyed.
And an owner who is actually available when you have a question.
How do you choose the right Windsor Hills rental?
This is where I think it helps to look beyond the number of bedrooms.
If you're a family of four, for example, a five-bedroom home might be more space than you need.
On the other hand, if you're travelling with grandparents, another family, or a larger group, having five bedrooms and five bathrooms can make a huge difference.
Think about how you actually vacation.
Do you want to spend a lot of time at the pool?
Is being close to the clubhouse important?
Do you want a quiet home with no rear neighbours?
Will you be cooking?
Do you need multiple bathrooms?
Will the kids want their own space?
These details can matter much more than saving $20 or $30 a night on the cheapest home you find.
What about resort fees and other costs?
This is another thing I recommend checking carefully before booking any Orlando vacation rental.
The advertised nightly rate isn't necessarily the amount you'll ultimately pay.
Look at the total cost of the stay, including cleaning fees, taxes, pool heat if applicable, and any resort or parking fees.
At our homes, we try to make the pricing as straightforward as possible, because nobody likes getting to the final booking screen and discovering a collection of unexpected charges.
If you have a question about what's included in either of our homes, [contact us directly →]. We're happy to explain it before you book.
Read the reviews—but actually read them
Don't just look at the star rating.
Read the reviews.
Look for recent reviews and pay attention to what guests repeatedly mention.
Are people talking about how clean the home was?
Did they sleep well?
Was the home accurately represented?
Did the owner respond quickly?
Were there surprises when they arrived?
Those details tell you much more than a beautiful listing photo ever can.
We've been incredibly fortunate to have wonderful guests leave us hundreds of reviews over the years, and honestly, those reviews mean more to us than any marketing description we could write ourselves.
Is Windsor Hills worth it?
For us, absolutely.
We've stayed in Orlando in different ways over the years, but Windsor Hills is where we chose to invest—not once, but twice.
It's close to Disney, the homes give families significantly more space than a traditional hotel room, and you have the flexibility of a private pool and full kitchen while still having resort amenities available.
But more than anything, I think Windsor Hills works because it gives families options.
You can spend the entire day at Disney.
You can spend the afternoon floating in your own pool.
You can cook dinner at home.
You can head to the clubhouse.
You can use Uber instead of renting a car.
You can do absolutely nothing.
And after a busy day in Orlando, that last one can be pretty wonderful.
Ready to find your Windsor Hills vacation rental?
If you're planning a Disney vacation and think Windsor Hills might be the right fit for your family, we'd love to have you stay with us.
Belle's
Our three-bedroom, three-bathroom Windsor Hills townhome is a great choice for families looking for a comfortable home close to Disney.
Motunui Villa
Our five-bedroom, five-bathroom Windsor Hills home sleeps up to 11 guests and gives larger families and groups plenty of room to spread out.
Both are homes we genuinely love, in a community we've chosen to invest in ourselves.
And if you're not sure which one is the better fit, just ask.
We're happy to help you figure that out.