Windsor Hills Resort vacation rental guide

Windsor Hills is a vacation-rental community in Kissimmee, Florida, on North Old Lake Wilson Road. Its pool, water park and clubhouse give guests options for days away from the theme parks. Check the home’s location within the community alongside its bedrooms and private facilities.

Pool, water park and shared facilities

The community lists a swimming pool, hot tub and water park, along with a fitness center, sports courts, playgrounds, game room and movie theatre. The Welcome Center is the place to ask about equipment and the activities available during your stay.

Compare shared amenities with what the home itself provides. A clubhouse pool is separate from a private pool, and a community movie theatre does not mean a rental has its own cinema room.

Registration and pool wristbands

The community’s guest resources require visitors to be registered in its access system before arrival. Drivers need the identification specified by the community, and guests should have reservation paperwork showing the property address ready for review.

Pool and water park wristbands are obtained through the clubhouse Welcome Center. Confirm how your host will register the group and what to bring when collecting them. Check current opening times before heading over.

Parking and arrivals

Ask how many vehicles are permitted for your reservation and which spaces you can use. The community prohibits parking on streets, grass or across sidewalks. Extra or oversized vehicles need their arrangements checked in advance.

Registration at the gate and access to the home are separate steps. Arriving at the community early does not confirm that the rental will be ready early. Follow the check-in time and instructions supplied for your booking.

Questions to settle before booking

• Is the guest list complete, including everyone arriving separately?
• Which bed arrangements, bathrooms and ground-floor rooms will your group need?
• Does the home have a private pool, and is heating available at an extra charge?
• How far is the home from the clubhouse, and will everyone be comfortable with that route?
• What parking, visitor and delivery arrangements apply during your stay?

Planning days around Kissimmee

Check driving routes from the actual home to the park entrances and other places on your itinerary. Traffic and parking can change the journey, so treat resort-wide estimates as a starting point.

Windsor Hills and Windsor Island are different communities. Check the full resort name and address before comparing a home’s location or the amenities shown in its photos.

Current community information

Use the community amenities page and guest-entry and parking rules, along with the Welcome Center’s amenity-access information. Your rental provider remains the contact for home-specific questions and reservation changes.

Plan your stay with Book Villas

Send your travel dates, group size and the facilities that matter to you. We can help you check the details of the options you are considering.

Read our Orlando planning guide and resort-access checklist before choosing a home.

Resort information checked October 30, 2026. Facilities and operating rules can change; confirm the terms for your home before booking. This is a Book Villas planning guide, not the resort operator’s website.