Windsor Hills Resort is a gated vacation rental community in Kissimmee, Florida, right on the southwest edge of Walt Disney World. This 2026 guide covers everything families ask about: location, drive times, amenities, rental types and how to book, with links to our detailed guides on each topic.
Location and Drive Times
Windsor Hills sits at 2600 N Old Lake Wilson Road, Kissimmee. Disney property is about 5 to 10 minutes away and Magic Kingdom about 10 to 12 minutes, depending on traffic. Orlando International Airport (MCO) is about 35 minutes. Read how close Windsor Hills is to Disney, driving to Magic Kingdom and the MCO guide.
Resort Amenities
- Heated lagoon pool, hot tub and toddler pool: see pool hours.
- Sir Windsor's AquaVenture water park with dueling racer slides and a giant splash pad (not heated).
- Clubhouse with a movie theater, games room, fitness center and Marketplace & Grille: see the clubhouse guide and gym guide.
- Playgrounds and splash pad: see the parents' guide.
- Sports: tennis, basketball, sand volleyball, pickleball and a putting green; see things to do at Windsor Hills.
- Security: a registered-guest-only gated community with a 24-hour staffed gatehouse.
Rentals: Condos, Townhouses and Villas
- 2-bedroom condos and 3-bedroom condos, some with pool views.
- 3-bedroom townhouses with private splash pools.
- 4-bedroom, 5-bedroom and 6-bedroom homes with private pools.
Not sure which fits? Read how to choose the right Windsor Hills rental.
Planning Your Stay
- 25 things to know before you arrive
- When to book for the best rates
- Is Windsor Hills worth it?
- Can you see Disney fireworks from Windsor Hills?
- Closest grocery stores and restaurants nearby
- Windsor Hills for UK families
Booking Windsor Hills
Most homes at Windsor Hills are privately owned. Booking directly with an owner can help you avoid platform fees and gives you a direct line to the person who knows the home best. See why families book direct with a Windsor Hills owner, and use the search below to find your rental.
