Windsor Hills Rest Day Guide Near Disney for Families
Are you looking for the perfect break between Disney park days? Whether you’re traveling with kids, friends, or your partner, a day off from the crowds can recharge your energy and make your trip even better. If you’re staying at Windsor Hills Resort in Kissimmee, you don’t even have to leave the property to relax.
At Chillax Inn, our private, family-friendly vacation rental within Windsor Hills provides you with all the space and amenities you need to unwind and truly enjoy your downtime. It’s a popular choice for families looking for a short-term rental near Disney World that offers both comfort and flexibility.
Here’s how to make the most of a rest day between your Orlando theme park visits, while still staying close to the magic.
Why Take a Rest Day During Your Disney Trip?
Walt Disney World is exciting, but it’s also non-stop. You’re waking up early for Genie+ reservations, waiting in lines, walking 20,000+ steps a day, and staying up late for fireworks. After a day or two of that, you need a break, and your kids do, too.
That’s where a rest day comes in. It helps your family reset, recharge, and avoid burnout, especially during extended stays in Central Florida.
Spending your rest day at Windsor Hills Resort means you’re still immersed in the vacation experience, but without the pace of the parks. You’re just 2 miles from Walt Disney World’s main gate, yet it feels like your own peaceful escape. It’s one of the reasons why many travelers choose a vacation rental near Disney over a traditional hotel stay.
If you’ve been searching for things like:
- “Where to stay near Disney with kids”
- “How to plan a Disney rest day”
- “Best resorts near Disney World for families”
—You’re in the right place.
Start the Morning Slow
Begin your day at a relaxed pace. No alarms. No park rush. No lines.
Take your time enjoying the Florida sunshine, sipping coffee from your patio or pool deck. At Chillax Inn, you’ll have a fully equipped kitchen, ideal for cooking a full breakfast or just whipping up simple bites like toast, eggs, or fruit bowls.
Want to head out for breakfast? You’ll find local favorites just a few minutes away in Kissimmee and Celebration, including:
- Dunkin’
- Starbucks
- Perkins Restaurant & Bakery
- IHOP in Celebration
This kind of freedom is why travelers prefer vacation homes near Disney World. You can cook when you want, eat when you want, and skip the crowded hotel buffet lines altogether.
Late Morning
By mid-morning, the weather’s perfect for outdoor time. One of the top reasons families choose Windsor Hills short-term rentals is the resort-style lagoon pool with:
- Giant water slide
- Zero-entry pool
- Interactive splash pad for little ones
It feels like you’re still at a theme park, but with fewer people and more space.
If you’re staying at a Windsor Hills rental with a private pool, like Chillax Inn, you can enjoy an even more peaceful experience. Swim with the kids, read in a shaded lounger, or float around in the warm water. This is what a Disney vacation with balance looks like.
What to bring:
- Pool towels
- Refillable water bottles
- Sunscreen
- Pool floats or toys
Lunch
When lunchtime rolls around, you can go the simple route and eat at home. Your Chillax Inn rental has everything you need to make a quick and easy lunch — from sandwiches and wraps to salads or hot meals.
Nearby grocery stores, including Publix, Target, and Walmart, are all within a short drive, making it easy to stock up.
Prefer to dine out? You’ll find plenty of family-friendly restaurants near Windsor Hills, including:
- Island Grove Wine Company (farm-to-table)
- The Wharf at Sunset Walk
- Ford’s Garage
- Flippers Pizzeria (also great for delivery)
- Chick-fil-A and Panera Bread are just up the road
Choosing a vacation rental near Orlando’s top dining spots gives you more control over your trip and your budget.
Afternoon
After lunch, take it slow. A rest day isn’t about doing nothing — it’s about doing what feels good.
The Windsor Hills Resort clubhouse offers plenty of low-key activities, including:
- Multiple playgrounds
- Game room for kids and teens
- Mini movie theater
- Basketball and tennis courts
- Fitness center for active travelers
If you’re craving total downtime, your rental is the best place to be. Whether you’re traveling with toddlers, teens, or adults, there’s room to relax.
Popular indoor ideas:
- Nap in a private bedroom
- Family movie marathon
- Streaming shows on smart TVs
- Board games or puzzles
- Reading time by the pool
It’s this mix of fun and quiet that makes Windsor Hills rentals with private amenities perfect for recharging.
Optional Mini Outing (If You Want to Get Out)
If you’re feeling a little restless, there are some low-key places to explore near Windsor Hills that won’t take up your whole day.
Easy outings include:
- Old Town Kissimmee– Vintage rides, snack stands, and family shops
- Downtown Celebration– Beautiful walking paths and lakeside cafes
- Disney Springs– Great for shopping, cupcakes, and people-watching
You’re still on vacation, but without the hustle. This balance is why many families search for relaxing vacation ideas near Disney World when planning longer stays.
Dinner and Wind Down
The evening is when your short-term rental truly shines. You can make dinner your way, whether that’s grilling by the pool, ordering takeout, or heating leftovers.
Want to make it memorable?
- Eat outside on the patio as the sun sets
- Let the kids enjoy a twilight swim
- Watch a movie to get excited for the next park day
No waitlists. No noise. Just your family and the rhythm of your schedule.
Why Book Your Windsor Hills Stay at Chillax Inn?
If you’re browsing vacation rentals in Windsor Hills, here’s why Chillax Inn stands out among other family-friendly Disney-area rentals:
- Private screened-in pool and outdoor lounge
- Smart TVs, fast Wi-Fi, and family-sized dining areas
- Fully equipped kitchen and laundry
- Multiple bedrooms for space and privacy
- Access to Windsor Hills Resort’s top-tier amenities
- 24/7 gated entry and security
- Located just 2 miles from Walt Disney World
It’s not just a place to sleep, it’s a place to live during your trip. Many families who book direct vacation rentals near Disney World say it’s the key to a smoother, more affordable vacation.
Your Windsor Hills Rest Day Itinerary
Here’s your no-pressure plan for a non-park day:
Morning: Sleep in, enjoy a relaxed breakfast
Late Morning: Head to the resort pool or swim in your private one
Lunch: Eat at home or nearby
Afternoon: Explore the resort, take a nap, or stream a movie
Evening: Dinner, night swim, or wind down early
It’s a perfect day that helps you feel refreshed and ready for your next Disney adventure.
Book Direct for the Best Value
Looking for a Windsor Hills vacation home near Disney World? Avoid third-party booking fees and book direct at chillaxinn.com
When you book direct:
- You get the best available rate
- No hidden fees or surprises
- Instant confirmation
- Personalized service from the owner
Many guests come back year after year because they love the balance of Disney excitement and resort relaxation. Join them and make Chillax Inn your go-to Disney-area vacation rental.
