Your Guide to Family-Friendly Restaurants Near Windsor Hills Resort
Planning a family getaway to Windsor Hills Resort in Kissimmee, Florida? You’re in for sunshine, theme parks, lazy mornings by the pool, and some starving kids after a day of fun. One of the top perks of staying in a Windsor Hills vacation rental is having plenty of nearby dining options. But where should you eat?
Whether you’re craving pancakes, deep-dish pizza, tropical flavors, or classic burgers, this guide will take you through the best family-friendly restaurants near Windsor Hills Resort, all of which are set to open in 2025 and are perfect for both dine-in and takeout.
Why Families Love Windsor Hills Resort
Windsor Hills is one of the most sought-after short-term rental communities near Disney World. It’s just 2 miles from the entrance to Walt Disney World, making it a convenient and popular choice for families wanting space, privacy, and proximity to Orlando’s top attractions.
Why it’s ideal for families:
- Spacious vacation homes with full kitchens and laundry
- Gated resort community with 24/7 security
- On-site amenities: lagoon-style pool, splash zone, movie theater, fitness center, and game room
- Easy access to local restaurants, grocery stores, and delivery services
Having your rental means flexibility, you can cook meals, eat out, or do a bit of both. And when you do eat out, these local spots make feeding your crew stress-free.
Top Family Restaurants Near Windsor Hills Resort
Here are some of the most popular restaurants near Windsor Hills Resort that families love. These are perfect for when you want a break from cooking or want to enjoy local eats together.
1. Flippers Pizzeria – 5 Minutes Away
A go-to for brick oven pizza near Windsor Hills, Flippers offers handcrafted dough, high-quality toppings, and fast service. The family combo meals are great for groups, and the menu also includes salads, pasta, and chicken wings.
Best for: Pizza night at the rental or a casual dine-in meal nearby.
2. Giordano’s – 10 Minutes Away
Known for authentic deep-dish pizza, Giordano’s delivers cheesy, satisfying pies that are perfect for families. The wait for a deep-dish pizza can be approximately 40 minutes, so it’s recommended to call ahead.
Kid tip: Ask for extra napkins—the cheese pull is real.
3. IHOP – 6 Minutes Away
Serving breakfast all day, IHOP is a reliable choice for families, especially those with younger children who love pancakes and waffles. The kids’ menu offers fun options, such as smiley-face pancakes, while adults can enjoy a variety of dishes, including omelets and burgers.
Pro tip: Visit on weekdays for possible “Kids Eat Free” offers.
4. Ford’s Garage – 12 Minutes Away
A unique, themed dining experience that looks like a retro garage, complete with vintage cars and gas station décor. The food matches the flair with stacked burgers, creamy mac and cheese, chicken tenders, and frothy milkshakes.
Fun factor: Great for Instagram-worthy family photos.
5. Bahama Breeze – 15 Minutes Away
Want something different? Bahama Breeze brings a tropical twist to your family vacation with Caribbean-inspired dishes like jerk chicken, coconut shrimp, and plantains. There’s also a kids’ menu and outdoor patio seating with live music.
Note: This location is confirmed to be open in 2025, although some others have closed.
6. The Cheesecake Factory – 20 Minutes Away
With an enormous menu, this is a great place when no one in the family can agree on what to eat. From flatbreads to tacos, pasta to salads, there’s something for everyone. And yes, the cheesecake selection is a must-try.
Popular pick: Oreo Dream Extreme Cheesecake.
7. Cracker Barrel Old Country Store – 15 Minutes Away
Southern comfort food and a general store rolled into one. Menu highlights include fried chicken, meatloaf, and hearty breakfasts—all available all day. Before or after your meal, browse the shop for nostalgic candy and toys.
Best for: A cozy, homestyle breakfast or lunch.
8. Sickies Garage Burgers & Brews – 15 Minutes Away
Famous for wild burger creations, this is the spot for adventurous eaters. The casual atmosphere, big TV screens, and arcade-style entertainment make it easy to keep kids occupied while waiting for food.
Must-try: Over-the-top milkshakes and unique dipping sauces.
9. El Tenampa Mexican Restaurant – 12 Minutes Away
A local gem serving authentic Mexican dishes like enchiladas, street tacos, and burritos. The portions are large, the service is friendly, and the colorful interior is welcoming for families.
Family tip: Great for affordable, flavorful dinners after a day at the theme park.
Need a Place to Recharge Between Meals & Parks?
Make your family vacation even smoother by staying at Chillax Inn, a top-rated Windsor Hills vacation rental. You’re just minutes from Disney and even closer to these kid-friendly restaurants.
Check out our Windsor Hills rest day guide to plan the perfect break between park days.
Quick & Convenient Eats Near Windsor Hills
Sometimes, you want something fast, familiar, and kid-approved. These spots are perfect for grabbing takeout or a quick dine-in bite close to your Windsor Hills rental.
- Chick-fil-A– Always quick, clean, and family-friendly
- Culver’s– Classic American food with frozen custard that kids love
- Panera Bread– Lighter meals like soups, sandwiches, and mac and cheese
- Panda Express– Fast, flavorful Asian cuisine that’s a hit with teens and tweens
Tips for Dining with Kids Near Windsor Hills
Here are a few helpful tips to make family dining easier while staying near Windsor Hills:
- Go early:Restaurants can get crowded around dinner time, especially during holidays or weekends.
- Look for deals:Some spots have discounted kids’ meals or family bundles.
- Call ahead:Especially for places like Giordano’s or Ford’s Garage, where seating and prep times can be longer.
- Use delivery apps:Uber Eats, DoorDash, and Grubhub offer access to many of these local spots. Perfect for tired evenings.
Make the Most of Your Windsor Hills Stay
One of the best aspects of staying in a Windsor Hills vacation rental is the freedom to mix in-home meals with restaurant nights. All rentals at Chillax Inn come with fully equipped kitchens, allowing families to balance their budgets and schedules.
Smart meal planning tips:
- Cook breakfast or lunch at home to save time before theme park days
- Schedule sit-down meals on your rest days or shorter park days
- Stock up on snacks and drinks at local grocery stores to keep kids fueled on the go
- Plan for a couple of fun restaurant nights to give everyone a break from cooking
Whether you dine out or dine in, the flexibility of short-term rentals gives you complete control over your family’s vacation experience.
Final Thoughts
When you stay at Windsor Hills Resort, you get the complete package: proximity to Disney, resort-style amenities, and access to the best family-friendly restaurants in Kissimmee. Whether you’re fueling up before a big park day or winding down after hours of adventure, these restaurants deliver convenience, quality, and variety.
Looking for the perfect place to stay?
Chillax Inn offers spacious, modern short-term rentals in Windsor Hills, ideal for families, groups, and anyone wanting a home base that feels just like home.
Browse and book our Windsor Hills vacation rentals now!
