If you have been researching where to stay for an Orlando trip, the name Windsor Hills comes up consistently in travel forums, family groups and recommendations from Latin American families who have already made the trip. It is not coincidence. Windsor Hills has a combination of location, amenities and property types that is hard to match in the area. This guide covers everything you need to decide if it is the right community for your family in 2026.
Windsor Hills is a vacation rental residential community located in Kissimmee, about 8 minutes by car from the main entrance to Walt Disney World. It is in Osceola County, surrounded by other vacation rental communities, and has controlled access with private security at the entrance.
What sets it apart from other communities in the area is the combination of three factors that few zones offer simultaneously: real proximity to Disney, its own water park inside the community and a variety of homes ranging from two-bedroom condos to nine or ten-bedroom mansions.
For international families traveling with kids of different ages, with grandparents or in large groups, that combination simplifies the trip logistics considerably.
All Windsor Hills properties include access to the community clubhouse, which has a level of facilities that exceeds many hotels in the area.
The most distinctive feature of Windsor Hills is its water park inside the community. It includes water slides, a lazy river, a main pool with a splash zone for young kids and seating areas with chairs and umbrellas around it. For families staying at Windsor Hills, having a water park steps from the house without buying additional tickets is a concrete advantage that reduces both cost and logistics.
On days the group decides to rest from the theme parks, the community water park handles entertainment without leaving the resort.
Beyond the water park, the clubhouse has additional pools, tennis courts, a children’s playground and a barbecue area. For groups spending several days, the variety of spaces keeps everyone busy on rest days.
The clubhouse has a game room with billiard tables, ping-pong and arcade games. Several home models inside Windsor Hills also have their own private game room within the property. For families with teenagers, this significantly changes the experience of free days.
Properties in Windsor Hills are independent vacation homes or townhouses, with private pools in most cases. Standard features include:
Properties range in size from 2 bedrooms for smaller groups up to 8 or 9-bedroom homes for large groups. Top Stay has several properties within Windsor Hills with different configurations, and the booking process is handled in Spanish with direct support.
The distance between Windsor Hills and Disney World is not just a marketing number. It has concrete implications for how the trip feels day to day.
Early arrival without heroics: leave the house at 7:30 am and be at the Magic Kingdom entrance by 8 am when the park opens. Families who achieve this have a one-hour advantage over those coming from more distant hotels.
Real midday return: the 12 pm to 3 pm block in summer or peak season is the hardest time in the parks. From Windsor Hills, going back to the house for lunch, eating comfortably and letting the kids rest for an hour is completely viable. From a hotel 30 or 40 minutes away, that return trip does not make logistical sense.
Total flexibility: if the group decides one day that they do not feel like the parks, they prefer the community water park or an afternoon of shopping, the proximity to Disney does not create pressure to “make it worth the distance.”
| Property type | Mid season | Peak season (summer, December) |
|---|---|---|
| 3-bed townhouse, shared pool | $130 – $180 per night | $180 – $260 per night |
| 4-bed home, private pool | $180 – $250 per night | $260 – $380 per night |
| 5-bed home, private pool | $220 – $310 per night | $310 – $460 per night |
| 6-8 bed home, private pool | $280 – $420 per night | $420 – $650 per night |
Booking directly with Top Stay rather than through third-party platforms eliminates additional commissions and allows direct communication in Spanish for any question or adjustment to the process.
Windsor Hills is not the only option in the area and not the right one for every situation.
Windsor Hills makes sense when:
Other communities may make more sense when:
Windsor Hills is a mixed-use community, with permanent resident homeowners and homeowners who rent their properties as vacation rentals. Both profiles coexist normally and the community is designed to manage this.
Yes. Windsor Hills does not have public transport connected to the parks or to downtown Orlando. A rental car is practically necessary for comfortable mobility.
Yes. Access to the clubhouse and the community water park is included in the vacation rental price. There is no additional charge for using those facilities.
For peak season (July, August, Christmas, Spring Break), 4 to 6 months in advance is ideal. Properties of 5 or more bedrooms are the first to sell out. For mid season (May, October, November), availability with 4 to 8 weeks’ notice is common in many cases.
It depends on the specific property. Some homes in Windsor Hills accept pets with additional charges and specific conditions. Top Stay can advise on which community properties have a pet-friendly policy.
After years of being the preferred community for international families in Orlando, Windsor Hills holds that position because the combination of location, in-community water park and property variety is hard to replicate. For a trip centered on Disney, with kids of different ages and a genuine intention to rest between park days, it remains the first option worth considering.
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