Windsor Hills Resort – A Top Choice for Orlando Vacation Homes with Private Pools
Planning a trip to the Orlando area and wondering where to stay? If you’re looking for resorts near Disney World that offer comfort, convenience, and exceptional value, Windsor Hills Resort deserves a spot on your radar. Often overshadowed by larger, more commercialized properties, Windsor Hills Resort is a gated community in Kissimmee that delivers big on family-friendly vacation experiences.
Located just 5 minutes from the gates of Walt Disney World, Windsor Hills Resort offers short term rentals near Magic Kingdom that blend privacy with resort-style amenities. Think spacious condos, townhomes, and pool homes near Disney World—all in a secure, beautifully maintained setting.
Why consider Windsor Hills Resort over traditional hotels or crowded resorts? It’s ideal for families or groups looking for more space and flexibility. Instead of squeezing into a hotel room, imagine having your kitchen, living area, and even a private pool. These family-friendly Orlando rentals are perfect for relaxing after a day of theme park adventures.
The community’s amenities rival many larger resorts. Guests enjoy a lagoon-style pool with water slides, a splash pad for kids, an on-site movie theater, and a modern fitness center. There are also tennis courts, a playground, and even a convenience shop within the gates.
From gated security to beautiful landscaping and family-focused amenities, Windsor Hills Resort truly is one of the best places to stay in Kissimmee. Its proximity to Universal Studios, SeaWorld, and other attractions makes it a hub for Florida vacationers.
Whether you’re searching for Kissimmee vacation communities or gated communities near Disney, Windsor Hills checks all the boxes.
Ready to discover more? Download our free Disney packing list and sample itinerary to help plan your perfect vacation, and explore everything Windsor Hills Resort has to offer.
5 Reasons Our Windsor Hills Vacation Home Is Perfect for Large Families
When traveling with a big family or group, finding the right place to stay can make or break your trip. Our 5-bedroom villa in Windsor Hills Resort is tailored to meet the needs of families who want both space and convenience near the magic of Disney.
- Room for Everyone: Our spacious vacation home rental in Windsor Hills comfortably sleeps up to 12 guests, with multiple bedrooms, full bathrooms, and generous common areas. It’s ideal for multigenerational trips or groups of friends.
- Private Pool & Outdoor Space: Enjoy your own Windsor Hills villa with a private pool—perfect for afternoon breaks between park visits or relaxing family dinners. You won’t need to fight for pool chairs like at large resorts.
- Family-Focused Amenities: From high chairs to strollers, board games to game consoles, we provide thoughtful extras that help families feel right at home. These small touches make a big difference for traveling families.
- Proximity to Disney: Located in the Windsor Hills gated community, we’re just 2 miles from Disney’s front gates. You won’t waste precious vacation time stuck in traffic, and early park access becomes much easier.
- Resort Perks Without Resort Prices: Get access to the Windsor Hills clubhouse, water park, fitness center, and more—all included with your stay, without the hefty resort fees you’d find elsewhere.
If you’re comparing Orlando resort options, our villa stands out as a top value-for-money choice. Guests consistently mention our home’s comfort, cleanliness, and unbeatable location in their Windsor Hills reviews.
Still not sure where to stay near Disney parks? Visit our Why Chillax Inn page to explore testimonials, a full list of amenities, high-quality images, and a proximity map showing just how close we are to the magic.
Packing Tips + Local Attractions Near Windsor Hills Resort
You’ve narrowed it down and are ready to book Windsor Hills Resort for your upcoming trip. Here are a few last-minute tips and nearby highlights to make your stay at Chillax Inn seamless and unforgettable.
Packing Tips:
- Bring swimsuits and sunscreen—you’ll want to enjoy your villa’s private pool and the community splash pad.
- Take advantage of the in-home washer/dryer and pack light.
- Don’t forget theme park essentials like portable chargers, reusable water bottles, comfortable shoes, and ponchos for those Florida showers.
- Include your favorite coffee and snacks—our fully equipped kitchen makes breakfast easy and affordable.
- For a complete guide on what to pack for your Disney World trip, check out our What to Pack for Disney World in Orlando blog.
Nearby Attractions:
- Walt Disney World: Just 2 miles away. You can be at the park gates in minutes.
- Island H2O Live! Water Park: A fun water experience close by that’s ideal for both adults and kids.
- Old Town Kissimmee: A classic boardwalk-style attraction featuring shops, rides, and weekly car shows.
- Margaritaville Resort & Sunset Walk: Great dining and entertainment options only a short drive from Windsor Hills.
- Shops & Dining on Highway 192: Everything from grocery stores to themed restaurants is right nearby, making meal planning easy.
Looking to finalize your plans? Check Chillax Inn availability and book direct to get the best rates and avoid third-party fees. Our affordable Kissimmee vacation rental is family-friendly, highly rated, and ready to host your magical getaway.
If you’re searching for a direct booking Windsor Hills rental or hoping to save on an affordable Kissimmee vacation rental, Chillax Inn offers a combination of comfort, location, and value that’s hard to beat.
Don’t just visit Orlando—Chillax like a local. Book your stay today!
