Disney World Christmas week is the hardest time of the year to find a vacation home, because families fill the best rentals months ahead. If you want a private pool, a full kitchen and plenty of bedrooms near the parks, book early and be ready to choose quickly. This guide covers when to book and what to check first.
Why Christmas week sells out
Schools are on break, extended families travel together, and everyone wants the same dates. Larger homes for big groups go first, because there are fewer of them. If your group is large, our guide to vacation rentals that sleep 10 or more shows what is possible.
When to book a vacation home for Christmas
As a rule, the earlier the better. Many families book many months ahead, and popular homes can be gone well before the fall. If your dates are firm, reserve now and check the cancellation terms rather than waiting for a better deal. Our when to book Windsor Hills for the best rates article has more on timing.
What to look for in a Christmas rental
- A full kitchen for a holiday breakfast or dinner at home.
- Enough bedrooms and beds so nobody is sleeping on a couch.
- A private pool, which is great for the mild Florida days.
- A washer and dryer to keep luggage light.
- A gated resort with amenities for downtime.

Why Windsor Hills works for the holidays
Windsor Hills Resort sits about 10 minutes from Disney property, and Magic Kingdom is usually 10 to 12 minutes away depending on traffic. The gated resort has a heated lagoon pool, plus the Sir Windsor AquaVenture water park and splash areas. There is also a clubhouse, games room, gym and courts. Homes range from condos and townhouses to private-pool villas and large houses, so there is a fit for most groups.
Book direct and save the hassle
Booking directly with an owner gives you a clear contact and clear terms. Read about why booking direct is worth it before you decide. Remember there is no resort shuttle to Disney, so plan on a rental car or rideshare for park days.
Secure your Christmas week at Windsor Hills
If Christmas week is on your calendar, do not wait. Browse Windsor Hills rentals, compare homes by size and pool, and book the one that fits your family before it is gone.




