Winter at Windsor Hills is mild and sunny most days, with cooler mornings and evenings that make the resort feel relaxed rather than hot. Central Florida weather can vary, so pack layers, check the forecast before you travel, and plan a mix of park days and easy days at the resort.
What winter weather feels like
Days are often pleasant, while mornings and nights can turn chilly. Bring light layers for early starts and evenings, plus swimwear for warmer afternoons. Our packing list for fall and winter weather has a full checklist.
Winter at Windsor Hills: pool days
The 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. See why the heated pool matters in winter for more. The Sir Windsor AquaVenture water park and splash areas are there too; check current availability before you count on them.
Easy outdoor activities
- Putting green: a quick, low-effort game for all ages.
- Tennis, basketball and volleyball courts: see our courts guide.
- Playgrounds and walking paths around the grounds for kids who need to burn off energy.
- Picnic spots and grills for a casual outdoor meal.
Indoor options when it's chilly
On a cooler or rainy day, head to the games room and arcade. Our games room guide covers what kids can play. The gym and clubhouse are good for a change of pace, and your rental's full kitchen is made for hot chocolate and a movie night.
Parks and the resort in one trip
Disney property is about 5 to 10 minutes away by car, and Magic Kingdom is around 10 to 12, so it's easy to go out for a morning and come back for lunch and a rest. There is no resort shuttle, so plan on driving or a rideshare. Winter crowds and hours vary, so check Disney's website for current details.
Book your winter stay
Windsor Hills is a gated resort with condos, townhouses and private-pool homes, with room for big families. Book direct with an owner and ask about pool heat for your specific rental. When you're ready, browse Windsor Hills rentals.
