Welcome to Orlando! As your local guide from Global Vacation Rentals, my job is to help you put together an unforgettable trip, and that always starts with finding the perfect home base. Let’s talk about Windsor Hills Resort, a premier gated community that gives you the privacy and comfort of a vacation home plus all the fun of a full-scale resort.
Best of all? It’s located just two miles from Walt Disney World's main gate.
So, why isn't Windsor Hills just another place to sleep? It's where the heart of your vacation truly begins. Imagine a secure, beautiful community packed with resort-style fun, but instead of a cramped hotel room, you have the keys to your own spacious rental.
This place was literally built for families and groups who need more than a standard hotel can deliver. It’s that unique mix of community amenities and personal space that really sets the stage for an incredible trip.
Here’s the simplest way I can put it: you get all the perks of a top-tier resort without giving up the comforts of home. You can spend the morning splashing around in a massive community water park and then head back for a quiet afternoon nap or a swim in your own private pool.
It's this unique combination that has so many families coming back year after year. In this guide, I'll give you the complete picture of the resort's welcoming atmosphere and show you exactly why its layout and prime location make it the go-to choice for creating those lasting memories.
For families, the ability to switch between high-energy resort fun and quiet, private downtime is a game-changer. It transforms a hectic theme park trip into a truly relaxing vacation.
One of the biggest wins for Windsor Hills is its unbeatable proximity to the magic. Being just 5-10 minutes from the main Walt Disney World entrance means you can easily pop back to your rental for a midday break—a lifesaver for families with young kids. Less time stuck in traffic means more time actually enjoying your vacation.
Choosing the right time to visit can make a great trip even better. For a deep dive into visiting when crowds are low and the weather is perfect, check out our guide on Orlando's sweet spot from November through mid-December.
By the time you finish this guide, you’ll see exactly why Windsor Hills is the perfect launchpad for your entire Orlando adventure.
Alright, let's talk about the fun stuff—what you actually get to do at Windsor Hills when you’re not trekking through the theme parks. Think of the resort as your own private playground, loaded with amenities that transform a simple place to stay into a full-blown vacation experience. Honestly, your "rest days" here might end up being some of your favorites.
The heart of it all is the massive, 140,000-gallon lagoon-style pool. It's way more than just a place to swim. This is the community's social hub, where families kick back, soak up that famous Florida sun, and let the kids burn off whatever energy they have left. Thanks to its zero-entry access, it's perfect for toddlers to splash around safely.
Right next to the main pool is the star attraction for kids (and, let's be real, most adults): the Sir Windsor AquaVenture water park. This isn’t some dinky hotel splash pad. We're talking two thrilling dueling water slides that will have your kids racing each other down again and again for hours.
I’ve had so many guests tell me their children had just as much fun here as they did at the big Orlando water parks. And the best part? It's completely included with your stay. No extra tickets, no long lines—just pure, simple fun a few steps from your front door. It’s an incredible value that really makes Windsor Hills stand out.
The resort’s clubhouse is basically central command for all on-site entertainment and relaxation. It’s where you’ll find everything you need to keep the entire family happy, no matter their age or mood.
As someone who lives and breathes Orlando, I always tell families to schedule at least one full "resort day." Don't just pack your itinerary with theme parks from sunup to sundown. A day spent just enjoying the free amenities at Windsor Hills is often one of the most relaxing and memorable parts of the entire trip.
For anyone who likes to keep moving, Windsor Hills has a fantastic lineup of sports facilities. You don’t have to press pause on your fitness routine just because you’re on vacation. The modern, state-of-the-art fitness center has everything you need for a solid workout.
Outside the gym, you’ll find well-maintained courts for just about everyone. Challenge the family to a game of tennis or basketball, or get a sand-between-your-toes workout at the sand volleyball court. There’s even a putting green to practice your short game before hitting one of the local championship courses.
Most importantly, all this fun happens inside a secure, protected bubble. The 24/7 guarded and gated entrance provides genuine peace of mind. Only registered guests and authorized visitors are allowed in, ensuring the community remains a safe sanctuary for your family. This level of security is a huge reason why families, especially those with little ones, choose Windsor Hills year after year. It just lets everyone relax and enjoy their vacation without a single worry.
You've seen all the amazing things to do at the resort, so now let's find the perfect home base for your crew. My goal here is to be your personal vacation home matchmaker—to help you sift through the options and land on a rental that feels like it was built just for you.
Windsor Hills was designed with different kinds of families and travel styles in mind. We'll break down the three main accommodation types so you can pick the right one with total confidence.
This little visual guide is a fun way to think about how you'll spend your resort days, whether the plan is to hit the waterpark hard, chill by the pool, or enjoy some indoor fun.
As you can see, the resort offers distinct paths for pure relaxation, high-energy play, and indoor entertainment, catering to whatever mood strikes.
For larger families, multi-generational getaways, or a few families vacationing together, the 4 to 6-bedroom private pool homes are the absolute gold standard. Think of them less as houses and more as your own private, self-contained vacation hubs.
Imagine having your own screened-in pool and spa just a few steps from your living room. The kids can splash around for hours while the adults kick back on the patio. Inside, you get multiple master suites, big common areas, and often a game room, giving everyone plenty of room to spread out and find their own corner.
These homes are the ultimate choice for groups who really value both togetherness and personal space. And if your party is even bigger, you're in luck. Check out our guide on 10-bedroom Orlando villas for large groups to see just how big you can go.
The townhomes at Windsor Hills are a fantastic middle ground, hitting that perfect sweet spot between space and value. They typically offer 3 bedrooms, which is ideal for a single family or a smaller group that just wants a bit more room.
Each townhome comes with its own private, screened-in splash pool—just the thing for a quick, refreshing dip after a long day at the parks. You get far more space and privacy than a condo without the full footprint of a large single-family home. It’s a smart, comfortable, and incredibly popular choice.
For couples, small families, or a few friends traveling together, the 2 and 3-bedroom condos deliver incredible convenience and value. They're located in buildings with elevators, which makes access a breeze, and they are often the closest rentals to the main clubhouse and resort pool.
Don't mistake these for standard hotel rooms. Each condo has a full kitchen, a comfortable living area, and private bedrooms, giving you all the essentials of a real home away from home. Best of all, you get full access to every single resort amenity, making it a budget-friendly way to get the complete Windsor Hills experience.
To help you decide at a glance, here's a quick breakdown of what each rental type offers.
Use this quick comparison to find the perfect rental type for your travel party's size and vacation style.
| Accommodation Type | Bedrooms | Best For | Key Feature |
|---|---|---|---|
| Private Pool Home | 4 to 6 | Multi-gen groups, multiple families | Large private pool, spa, and game room |
| Townhome | 3 | Single families, smaller groups | Private splash pool, great value |
| Condo | 2 to 3 | Couples, small families, budget-conscious | Proximity to clubhouse, affordability |
Ultimately, there's no "wrong" choice here—just the one that's right for your trip.
When you start browsing different listings, it helps to know what to look for in a description to ensure you’re getting a clear picture of the property. Having some background on what makes for effective property description examples can help you read between the lines and pick a winner.
Let's be honest, you're coming to Orlando for the world-class attractions. I've been doing this for years, and I can tell you that location is everything. This is where Windsor Hills Resort really sets itself apart, and I want to give you the real-world drive times, not just what a map app might guess.
The resort's proximity to Walt Disney World isn't just a convenient bullet point—it's a genuine game-changer for your entire vacation. Windsor Hills is just two miles from the main gate, which means you can get from your front door to a Disney parking lot in as little as 5 to 10 minutes.
That's often faster than the bus ride from some of Disney's own value resorts! This means you can easily pop back to your rental for a midday swim, a nap for the little ones, or just a quiet lunch away from the chaos. It's the secret to preventing that all-too-common theme park burnout.
Having that flexibility makes your days so much more enjoyable and relaxing. Here’s a quick breakdown of what to expect for drive times to the major parks:
So, what’s the best way to get from the resort to the parks? You've got a couple of great options, and the right one really just depends on your group’s budget and vacation style.
The Freedom of a Rental Car
Having your own car gives you the ultimate freedom. You can leave for the parks on your schedule, make a spontaneous Target run, or explore beyond the main tourist corridor. A huge perk is that parking is completely free at your Windsor Hills rental. After a long park day, having a car means you can easily go check out some of the cult-favorite restaurants near Disney that locals love.
The Simplicity of Ridesharing
Services like Uber and Lyft are super convenient and always available at Windsor Hills. A standard ride to a Disney park usually costs between $10-$20, depending on the time of day and demand. This is a fantastic choice if you want to skip the theme park parking fees (which are often $30+ per day) and the long walk from the parking lot to the entrance.
My Insider Tip: When you're heading to Universal, try to avoid the infamous I-4 traffic by using local backroads like Turkey Lake Road or Apopka-Vineland Road. Your GPS will often suggest these routes during peak hours, and listening to it can easily save you 20 minutes of sitting in a standstill.
Ultimately, whether you rent a car for total control or use rideshare services for door-to-park simplicity, getting around from Windsor Hills is refreshingly easy. The resort’s strategic location is designed to make sure your journey to the magic is always quick and hassle-free, giving you more time to actually enjoy your vacation.
Alright, let's get you booked. The goal here is to make reserving your Windsor Hills home as simple and stress-free as the vacation itself. I want to give you the insider strategies to not only lock in the perfect rental but to do it smartly, sidestepping the common mistakes and hidden fees.
If I can give you one single piece of advice, it's this: book directly with a trusted management company like us at Global Vacation Rentals. When you book on those giant third-party travel sites, you're almost always paying hidden service fees that can seriously inflate the cost. Booking direct cuts out that middleman, which means you get access to the best possible rates.
Even better, it gives you a direct line to a local team that actually knows these homes. We manage them, we're in them, and we know them inside and out. That means you get a genuine guarantee of quality and a real person to call if you have a question or need anything during your stay.
Timing your trip can make a massive difference, both for your wallet and your overall experience. Orlando is fantastic year-round, but a few specific windows offer that perfect blend of great weather and lighter crowds. We locals call them the "shoulder seasons," and they're my personal favorite times to enjoy the parks.
Now, for major holidays like Christmas, Easter, or Thanksgiving, all the normal rules go out the window. These are peak travel times, and the best homes get snatched up incredibly fast. As a rule of thumb, you should plan to book your holiday stay at least 9 to 12 months in advance to have the best selection. That said, it's not impossible to find a great last-minute spot, as we cover in our guide for a last-minute Thanksgiving trip to Orlando.
Here's something I always tell friends: booking a vacation home isn't like booking a hotel. You're reserving a specific, one-of-a-kind property, not just one of a hundred identical rooms. Once it's gone, it’s gone for good.
We want your arrival day to be completely seamless, with no nasty surprises. Our check-in process is designed to be as simple as possible. Before you even leave home, you'll receive your door access codes and all the specific details for your rental. This lets you drive straight to your vacation home and get your vacation started immediately—no front desk, no lines, no hassle.
It's also important to know about the optional costs upfront so you can budget perfectly. Unlike hotels that often hit you with mandatory "resort fees," the only potential extra charges at Windsor Hills are for services you actually choose to add.
The most common ones are:
By planning ahead and booking smart, you can get every detail sorted out ahead of time. All that’s left for you to do is count down the days until your Orlando adventure begins.
As we wrap up our little tour of Windsor Hills, I want to tackle some of the questions I hear all the time from families just like yours. After years of helping people plan their perfect Orlando vacation, you start to notice the same things come up again and again.
Think of this as our final chat before you start packing. My goal is to clear up any lingering questions so you can feel totally confident and just plain excited for the trip ahead. Let's get right to it.
Yes, and honestly, this is the mic-drop feature of the resort. It's the number one reason families choose Windsor Hills. The main gate is just two miles from Walt Disney World property.
What does that mean in real-world time? A 5 to 10-minute drive to Disney's main entrance. I'm not kidding when I say that's often faster than waiting for and riding a bus from some of Disney's own value resorts. The ability to pop back to your own place for a midday nap or a swim without a huge travel ordeal is an absolute game-changer, especially with little ones.
You absolutely can, and you absolutely should. It's one of my top tips for starting your vacation off right. Services like Instacart, Amazon Fresh, and Shipt all deliver right to your front door.
The security team at the gate is completely used to seeing them and will wave them right through. You can even time your delivery for shortly after you arrive, so you walk into a fully stocked kitchen. It saves you from wasting a precious vacation afternoon navigating a crowded supermarket.
There's no better feeling than walking into your rental, grabbing a cold drink from a fridge you didn't have to stock, and jumping straight into the pool. It’s the ultimate vacation kickoff.
This is a great question because it highlights one of the best things about Windsor Hills. Unlike hotels that tack on a surprise $25-$45 (or more!) daily "resort fee," here, there is no mandatory daily resort fee.
When you book your stay, your access to all the community amenities is included. That means unlimited trips to the lagoon-style pool, the Sir Windsor AquaVenture water park, the movie theater, the gym, and all the sports courts are part of your stay. The only extra costs you might run into are optional things specific to your rental, like paying to heat a private pool or renting a BBQ grill for the week.
Your family's safety is a huge deal, and it's taken very seriously here. Windsor Hills is a fully gated community with a professional security guard on duty at the main entrance 24 hours a day, 7 days a week.
No one gets in without being a registered guest or an authorized visitor. This tight control creates a secure, peaceful bubble where you can truly relax and let the kids have a little freedom. It’s one of those intangible benefits that really sets the community apart from other Orlando-area rental options.
Ready to lock in the perfect home base for your family's Orlando adventure? The team here at Global Vacation Rentals is ready to help you find the Windsor Hills property that checks all your boxes. Booking directly with us means you skip the extra fees and always get the best possible rate.
