Windsor Hills vs Windsor at Westside is really a question of established vs new. Windsor at Westside is a newer Kissimmee vacation-home community, and Windsor Hills is a long-established resort right beside Walt Disney World. Despite the similar names, they are separate communities with different strengths.
Windsor at Westside's strengths
Westside's appeal is newness. Homes tend to have fresh finishes, and the resort has a large clubhouse, a pool with a lazy river and a water slide, a kids' splash area, a bar and lounge, a market and an arcade. For families who value the newest build above all, that's a real draw. Depending on the home and rental program, Westside may charge a separate fee for amenity access.
Location: Windsor Hills is next to Disney
Windsor Hills sits off Old Lake Wilson Road on the southwest edge of Disney property. Disney property is roughly 5 to 10 minutes away, and Magic Kingdom is usually about 10 to 12 minutes, depending on traffic. Westside is generally a bit farther from the Disney gates, so park mornings start with a longer drive. See how close Windsor Hills is to Disney for details.
Why an established resort is an advantage
- Mature landscaping and shade. Established palms and oaks make the streets and paths feel settled rather than new.
- A proven track record. Windsor Hills has hosted Disney families for years, and many owners have refined their homes over many stays.
- Room to choose. Condos, 3-bedroom townhouses with private splash pools, and houses and villas with private pools.
Water fun: water park vs lazy river
Westside has a lazy river, which some families love. Windsor Hills answers with Sir Windsor's AquaVenture water park: dueling racer slides, more slides and a giant splash pad, right next to the heated lagoon pool and hot tub. For kids who want speed and splashing, the water park usually wins. The clubhouse adds a movie theater, games room, fitness center and the Marketplace & Grill.
Which one fits your family?
Windsor Hills fits families who want the shortest practical drive to Disney, a real water park and plenty of home sizes. Windsor at Westside fits families who put a brand-new home first and don't mind a longer drive.
The verdict
Westside is a good newer option. For a Disney-first vacation, Windsor Hills offers what matters most on park days: location, a water park, and a settled resort that feels like a neighborhood. See Windsor Hills' location or book direct with a Windsor Hills owner.
