Vacation Homes Near Disney World Orlando
Orlando is famous for its world-class theme parks, shopping, dining, and outdoor activities. But when it comes to choosing where to stay, travelers want more than just a place to sleep. They want space, amenities, and a location that puts them close to the action while still giving them room to relax.
That’s where Windsor at Westside Resort comes in. Located in Kissimmee, this gated community has become a favorite among families, groups, and visitors to the Disney and Universal parks. Paired with the vacation rentals available through Chillax Inn, Windsor at Westside offers the perfect balance of fun, relaxation, and convenience.
In this guide, we’ll cover everything you need to know about Windsor at Westside Resort, what makes it unique, nearby attractions you shouldn’t miss, and tips for planning your Orlando getaway.
What Is Windsor at Westside Resort?
Windsor at Westside is a newer vacation rental community designed with resort-style amenities and spacious homes. Unlike traditional hotels, you’re not limited to one or two rooms. Instead, you can stay in large vacation homes with multiple bedrooms, private pools, and full kitchens — perfect for families or groups traveling together.
The resort itself feels like a destination. Guests enjoy:
- A massive resort-style pool with slides and a lazy river.
- A clubhouse with a fitness center, arcade, and lounge areas.
- Sports courts for basketball, volleyball, and soccer.
- On-site dining options, including a tiki bar.
- Walking paths and landscaped spaces for relaxation.
It’s a family-friendly community that blends the privacy of a vacation home with the perks of a resort stay.
Location: How Close Is Windsor at Westside to Orlando’s Attractions?
One of Windsor at Westside’s biggest advantages is its location. It’s in Kissimmee, just off Highway 192 and close to I-4, which makes reaching the area’s top attractions simple.
- Walt Disney World – About 15–20 minutes away.
- Universal Orlando & Epic Universe – Around 30–35 minutes.
- SeaWorld Orlando – About 25 minutes.
- Orlando International Airport (MCO) – Roughly 40 minutes by car.
This central location gives you access to all of Orlando’s theme parks without being stuck in crowded hotel zones.
Why Choose Windsor at Westside Over a Hotel?
Hotels near Disney are popular, but they often come with drawbacks: small rooms, limited amenities, and higher costs when traveling with groups. Windsor at Westside solves these issues by offering:
- Space for Groups – Vacation rentals can sleep 8 to 16 guests, making them perfect for large families or group trips.
- Private Pools – Most homes include screened-in pools and patios.
- Full Kitchens – Save money and time by preparing meals in your rental.
- Resort Amenities – Lazy river, fitness center, arcade, and more.
It’s a smarter option for travelers who want flexibility and value without sacrificing quality.
A Closer Look at Windsor at Westside Amenities
The resort is packed with activities for all ages. Here’s a breakdown:
- The Pool Area – The heart of the resort, featuring a lagoon-style pool, water slide, and lazy river. It’s the perfect spot for downtime after long theme park days.
- Clubhouse – Inside, you’ll find a gym, kids’ game room, and lounge areas for relaxing.
- Sports & Play – Volleyball courts, soccer fields, and basketball courts make it easy to stay active.
- Dining & Drinks – The on-site tiki bar offers snacks and refreshing drinks, so you don’t have to leave the resort when you need a bite.
These amenities add value to your stay, giving you more than just a rental home — you’re getting a complete resort experience.
Top Attractions Near Windsor at Westside Resort
While Disney is the big draw, there’s so much more to do near Windsor at Westside. Here are some must-visit spots:
Walt Disney World Resort
Magic Kingdom, EPCOT, Hollywood Studios, and Animal Kingdom are just minutes away. Staying at Windsor at Westside makes it easy to plan multiple park days while still having a home base nearby.
Universal Orlando & Epic Universe
Universal Studios, Islands of Adventure, and the soon-to-open Epic Universe are all within a 30–35 minute drive. For thrill-seekers, this is a must.
SeaWorld Orlando
Families love SeaWorld for its mix of marine life, rides, and shows.
Disney Springs
Not just for shopping, Disney Springs offers live entertainment and restaurants like The Boathouse and Wine Bar George.
Local Golf Courses
Providence Golf Club and ChampionsGate are both close by, offering championship courses for golf lovers.
Crystal River
If you’re up for a day trip, head to Crystal River to swim with manatees in their natural habitat. It’s an experience you won’t forget.
Dining Highlights
Guests often enjoy casual dining at Rock N Brews or exploring the many restaurants along Highway 192. From local BBQ to international cuisines, the area has something for everyone.
Tips for Families Staying at Windsor at Westside
Traveling with kids? Here are some ideas to make your trip easier:
- Plan downtime days at the resort to balance out theme park visits.
- Use your rental’s kitchen for quick breakfasts before heading out.
- Pack snacks and drinks for long park days.
- Take advantage of the game room and pool to keep kids entertained without leaving the resort.
When Is the Best Time to Visit?
Choosing the right season can shape your experience:
- Spring & Fall – Lower crowds and pleasant weather.
- Summer – Great for families with school-aged children, though expect hotter weather and more visitors.
- Winter Holidays – Orlando is magical this time of year, but book early as demand is high.
A Sample 5-Day Itinerary from Windsor at Westside
To help you picture your stay, here’s a simple itinerary:
- Day 1 – Arrive at Windsor at Westside, unpack, and relax by your private pool.
- Day 2 – Spend the day at Magic Kingdom. Return for an evening swim.
- Day 3 – Enjoy Universal Studios or Epic Universe.
- Day 4 – Take a break at the resort. Float along the lazy river, play volleyball, and dine at the tiki bar.
- Day 5 – Explore Disney Springs or visit Crystal River before heading home.
This mix of high-energy attractions and resort relaxation helps you get the most out of your trip.
Why Book with Chillax Inn?
When you choose Windsor at Westside through Chillax Inn, you’re not just booking a house. You’re getting a vacation experience tailored for groups and families. Chillax Inn properties are well-maintained, designed for comfort, and located in prime resort communities.
You’ll enjoy:
- Clean, spacious homes with modern amenities.
- Access to all Windsor at Westside resort features.
- The privacy of a vacation rental with the perks of a resort.
Booking through Chillax Inn means peace of mind, so you can focus on making memories.
Final Thoughts
Windsor at Westside Resort is more than a place to stay; it’s a destination that enhances your Orlando vacation. With its combination of private vacation homes, resort-style amenities, and unbeatable location near Disney and Universal, it’s a top choice for families and groups.
Pair your stay with a property from Chillax Inn, and you’ll have the perfect balance of relaxation and adventure. From poolside afternoons to theme park thrills, Windsor at Westside puts you in the heart of it all.
Ready to start planning? Book your Windsor at Westside stay today and discover why so many guests call it their favorite Orlando retreat.
