Windsor Hills is a beautiful, family-friendly, gated resort community in Kissimmee, Florida (south of Orlando). Situated only two miles from Walt Disney World® Resort, it’s located within easy reach of most of Orlando's top attractions. The Windsor Hills villas each have private, screened-in pools in addition to the fabulous community pool and kids’ water park. This secure, 24/7 guarded community has everything and more for your family vacation.

View our Featured Windsor Hills Private Vacation Rentals at the bottom of this page.

Some of Windsor Hills’ notable features include a luxurious zero-entry pool, water park with fountains and water slides, a hot tub/spa, and a toddler splash pad. There are plenty of recreational areas, including tennis, basketball, and volleyball courts for everyone. There’s even a putting green! Windsor Hills also features multiple playgrounds for the children, including a large castle-style playground.

The enormous Windsor Hills clubhouse overlooks the double Olympic-sized swimming pool and houses billiards tables, a video game area, a marketplace with grill, a fitness room with top of the line fitness equipment, a high definition surround sound movie theater, and other outdoor recreational activities. It’s a relaxing, playful atmosphere for the entire family!

No other private vacation home rental community in this area has what Windsor Hills has to offer, which is why it is the number one resort for many visitors. The facilities are as good as anywhere in the Orlando/Disney area, and you won't have to break the bank to enjoy them.

All Windsor Hills vacation rentals are located less than 10 minutes from Walt Disney World, just one mile from the attraction-packed Highway 192, less than a mile from a Walmart Supercenter and gas station, about 2.5 miles from I-4, and 10 minutes from Celebration, the community designed and built by Disney. There are plenty of dining and shopping options nearby.

Universal Orlando Resort is about 21 minutes away, and Sea World about 19 minutes, traffic permitting. Kennedy Space Center at Cape Canaveral is just over an hour away. In the other direction, Clearwater Beach is about an hour and a half drive.

There are several golf courses within easy reach, including Mystic Dunes, a 72-par public course designed by Champions Tour Player and NBC Golf Analyst Gary Koch. It’s literally a five minute walk away. Legends course at Orange Lake (5 minute drive) and the beautiful course at Celebration (15 minute drive) are also nearby.

The Windsor Hills resort is home to approximately 320 condos, 210 townhomes, and 470 single-family homes spread across a beautifully maintained and landscaped community. Their 24 hour manned gates and computerized security system track every guest, visitor, and delivery that enters the community, providing a safe and secure environment for your family vacation.

Windsor Hills Resort Amenities

• Lagoon-style swimming pool and waterpark complex
• State-of-the-art fitness center
• Marketplace with groceries, sundries, and grill
• Welcome center and guest services
• Game room with billiards and ping pong
• Clubhouse with cyber café and video arcade
• Private high-def surround sound movie theater
• Tennis, basketball, and volleyball courts
• Children's playground
• Putting green for golfers
• Picnic and BBQ area
• 24-hour gated, guarded entrance
• DVD rentals
• ATM

There is no denying the reputation this resort has earned is well deserved and will ensure that the Windsor Hills private villas remain one of the top destinations for Orlando family vacations for many years to come.

Windsor Hills Resort Address

2600 N Old Lake Wilson Rd.
Kissimmee, FL 34747