Disney World in winter with young kids can be easy and fun if you plan around three things: layers, naps and pool time. Mornings and evenings can feel cool while afternoons are often mild or warm, so dress kids in easy-to-peel layers, build a rest into the middle of the day, and use your rental's pool for a gentle afternoon reset. Staying at Windsor Hills makes that rhythm simple, because Disney property is about 5 to 10 minutes away by car.
Layers that work from morning to afternoon
Central Florida winter weather swings, so check the forecast before you pack and again the night before each park day. Think in layers rather than heavy coats:
- A short-sleeve shirt as the base layer, since afternoons can be warm.
- A light long-sleeve top or zip-up sweatshirt for early mornings and evenings.
- A light rain jacket that folds small, because showers can pop up.
- Comfortable sneakers and an extra pair of socks for each child.
- Swimsuits packed in the carry-on, so pool time is ready when you are.
Our packing list for fall and winter weather has a full checklist to work from.
Protect nap time on Disney days
Little kids melt down faster when they're tired, and winter days end earlier than you'd think. A simple plan helps:
- Go early, when lines and temperatures are gentler, and head out around lunchtime.
- Let toddlers nap in the stroller in a shady spot, or drive back for a real nap in a real bed.
- Keep one park day per two or three days a lighter one, with a short visit or no park at all.
Because the drive is usually under 15 minutes, a midday trip back to your rental is realistic. There is no resort shuttle, so plan on driving or a rideshare. If your kids are about five, our guide to Disney with a 5-year-old covers naps and rides in more detail, and our car seat and stroller guide helps you decide what to bring.
Pool time on cooler days
Pool time is a great way to burn off energy between park days. The Windsor Hills lagoon resort pool is heated, which takes the edge off cooler days. Most Windsor Hills owners now include private pool heat at no charge for homes with their own pool, but confirm with the owner before booking. Read why the heated pool matters in winter for more. The Sir Windsor AquaVenture water park and the splash areas are also on site, and our playground and splash pad guide shows what little ones can do there. Check current availability before you count on them, and keep towels and dry clothes handy.
Easy evenings at the rental
A full kitchen means you can make simple dinners, warm milk and hot chocolate on your own schedule instead of waiting for a table with a tired toddler. Condos, townhouses and private-pool homes at Windsor Hills offer room for big families, and the gated resort adds a calm feel. Clubhouse, games room, gym and courts give older siblings something to do while little ones wind down.
Plan Disney World in winter with young kids
Winter crowds, hours and special events change from year to year, so check Disney's website for current details. Book direct with an owner and ask about pool heat for your specific rental. When you're ready, browse Windsor Hills rentals.
