Windsor Hills Resort
Windsor Hills is a gated community of 999 individually owned condos, townhouses and houses near Kissimmee in Central Florida, typically a 10 to 15 minute drive from the Walt Disney World parks. Rather than a hotel, it’s a spread of self-catering holiday homes, let by many different owners, that share a zero-entry lagoon pool, a small water park and a clubhouse with a cinema and games room. Families come for the space and a kitchen of their own, often with a private pool, close to the parks.
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Is it worth it?
Windsor Hills suits families who want the space of a whole home near the parks and are happy to drive and cook.
Windsor Hills isn’t a hotel. It’s a gated community of 999 individually owned condos, townhouses and houses near Kissimmee, typically a 10 to 15 minute drive from the Walt Disney World parks and closer still to Disney’s Animal Kingdom. The draw for families is space and a kitchen, often with a private pool of your own, plus a shared zero-entry lagoon pool and a small water park. What you give up is hotel service, so you cook and clean up yourself, there’s no crèche, and because every home is owned and let separately, the standard of any one home and its booking terms vary from owner to owner.
Best for
You want the space and kitchen of a self-catering condo, townhouse or private-pool house close to the Disney parks, and you’re happy to drive.
Maybe not for
You want a hotel room with daily housekeeping, an airport transfer and no car, or supervised childcare for a baby or a younger toddler.
Best ages
Works across the ages, with the zero-entry pool, splash pad and toddler pool for little ones and a games room, cinema and playgrounds for older children. Nothing is laid on for babies specifically.
What stands out
Being among the closest gated communities to the Disney parks, with a zero-entry lagoon pool and a small water park inside the gates.
What to check
Because each home is individually owned and managed, confirm the exact terms, fees and any baby kit with your own owner or manager before you pay.
Where is it?
A gated community off US-192 in Kissimmee, Central Florida, typically 10 to 15 minutes from the Disney parks and about 30 to 35 minutes from Orlando airport.
Quick facts for families
A gated community near the parks
Windsor Hills sits close to Disney, and its homes are owned and let one by one, not booked from a single desk.
Windsor Hills sits on the west side of the Walt Disney World area, off US-192 in Kissimmee, in the same villa belt covered in our Orlando guide. It’s a gated community of 999 homes built from 2005, a mix of 320 condos in low-rise and mid-rise buildings, 210 townhouses and 469 detached houses, wrapped around a clubhouse, a lagoon pool and a water park. A homeowners’ association runs the shared clubhouse, pools and grounds and staffs the gate; it doesn’t run the bookings.
For distances, it’s among the closest such communities to the parks. It’s typically a 10 to 15 minute drive to any of the four Disney parks, and closer still, around 5 to 10 minutes, to Disney’s Animal Kingdom. Orlando International Airport (MCO) is about 30 to 35 minutes away, and Universal Orlando and SeaWorld are each roughly 20 to 25 minutes. There’s no resort shuttle to any of it, so a hire car is essential.
No single booking deskHow booking works
Windsor Hills has no single reservations desk. Every home is owned separately, and owners let their own out short-term, some through their own small booking sites, many through one of the dozens of Orlando holiday-home management companies, others through Airbnb, Vrbo or Booking.com. There is no central call centre for the community as a whole; the clubhouse phone number reaches the association’s side, not a bookings line.
What this means for a family is that the home itself, its decor, how well it’s kept and how quickly a maintenance problem gets sorted, varies from owner to owner, even between two condos in the same building. The booking terms vary too. The minimum stay, the check-in day (some homes are Saturday to Saturday only), the cancellation terms and whether a cot, high chair or pool fence comes with the home are all set by the individual owner, not the resort, so there’s no community-wide policy to quote. Read the specific home’s own terms, and if something matters for a baby or toddler, a stairgate, a fenced pool, a travel cot, ask that owner or manager directly before you book. Many owners set a minimum age of 25 to rent, so check the specific home’s terms. Because several management companies each list their own homes, the same community turns up on review sites under several different names with separate scores, though it’s all one place.
Check it’s Windsor Hills, not Windsor Island
Windsor Hills and Windsor Island Resort are two separate communities that share the Windsor name and a similar set-up, a gate, a clubhouse, pools and waterslides, which is a well-known source of booking mix-ups. Windsor Island sits in Davenport, in a different county and a good bit further from the parks, where guests report 30 minutes to an hour or more to Disney parking in traffic, against Windsor Hills’ much shorter run. Check the home’s address and community name before you pay, so you get the one you mean.
Condos, townhouses and houses
The three home types are lift-served condos by the pool, townhouses with a small plunge pool, and detached houses with their own pool and room for a big group.
There’s no hotel room at Windsor Hills. The smallest thing you can book is a condo, and it scales up through townhouses to detached houses, all self-catering with a full kitchen, which is the practical heart of the appeal for a family cooking most meals in. There’s no single official size sheet, since every home is owned separately, so exact floor areas vary home to home and the home’s own details are the place to check what you’re getting.
| Home type | Layout | Private water | Good to know |
|---|---|---|---|
| Condos (320) | 2 or 3 bedrooms, 2 bathrooms, on one level | Shared pools only | Closest to the clubhouse and pools, with lift access and wide doorways, the easiest type for a pushchair |
| Townhouses (210) | 3 bedrooms, 3 bathrooms over two floors | A small private splash plunge pool | A short walk from the clubhouse, stairs only, sleeps up to eight |
| Houses (469) | 4 to 6 bedrooms, occasionally 7 | A private screened pool, plus a spa on larger homes | Spread around the community, room for a big group, some with a games room |
The step-free options, and the private pools
Condos are the most step-free type. All eight condo buildings have both stairs and a lift, with extra-wide doorways, so a pushchair goes straight up, and each condo is on one level with a full kitchen, a washing machine in the condo and a balcony or patio. They’re 2 or 3 bedroom, 2 bathroom, and sit closest to the clubhouse and pools; there’s no private pool, so you use the shared lagoon pool and water park a short walk away.
Townhouses are all 3 bedroom, 3 bathroom over two floors, one bedroom and bathroom downstairs and two bedrooms up, sleeping up to eight, a short walk south of the clubhouse. Each has its own small private splash plunge pool in a screened porch, or lanai, smaller and shallower than a full swimming pool, which can usually be heated for an owner-set extra charge in the cooler months. Being on two floors with stairs only, they’re less convenient than a condo for a pushchair, though fine for a toddler who can take the stairs with a hand held.
Houses run from 4 to 6 bedrooms, occasionally 7, each with its own private screened pool and, on the larger homes, a spa, plus a lanai for eating outside; the largest sleep 12 to 14. Layouts vary. The 4 bedroom single-storey villa is the one house style on a single level, which makes it the most step-free for a pushchair or anyone with reduced mobility, while the 5 and 6 bedroom homes put one or two bedrooms downstairs and the rest upstairs. Bigger houses often add a private games room, and some owners fit out themed children’s bedrooms with Disney characters, princesses, superheroes or racing cars. Both are an individual owner’s choice on a minority of homes, so treat them as a bonus of a particular house rather than something every one has.
If you book a townhouse or house with a private pool and you’re travelling with a baby or toddler, ask the owner what pool safety is fitted. Florida law has required a safety barrier, a fence, a self-latching gate, a door or pool alarm or a cover, on pools built since 2000, but that’s a building rule rather than a promise that a removable child fence is up and ready, and extra measures like that are often only there if you ask for them ahead of arrival.
The pools and water park
The shared pool and water park are the reason a lot of families pick Windsor Hills over a plain villa rental.
The main pool is a zero-entry lagoon pool, so it slopes in from the edge like a beach with no steps, which is easier for a toddler or a nervous swimmer to walk into. It holds 140,000 gallons, is heated year-round and opens 8am to 10pm every day, with a large hot tub alongside. Everyone needs a wristband, free from the Welcome Center in the clubhouse, for the pool and water park.
Sir Windsor’s AquaVenture is the small water park next to it. It has two large body slides that run side by side, two smaller slides and a splash pad, the shallow water-play area for younger children, and opens 10am to 8pm daily. Alongside the main pool and splash pad there’s a separate toddler pool for the youngest. Pool and water park hours can change for weather.
Eating in and nearby
Windsor Hills is self-catering, so most meals happen in your own kitchen, with the US-192 restaurant strip a short drive away.
Every condo, townhouse and house has a full kitchen, and the community is built around families cooking at least some meals in. The only food on site is the Marketplace & Grill in the clubhouse, a small convenience shop and a casual grill counter, open 10am to 8pm; there are no sit-down restaurants inside the gates.
For everything else you drive. The US-192 corridor and the Formosa Gardens area a mile or two away have a wide spread of casual and chain restaurants, Outback Steakhouse, Red Lobster, Buffalo Wild Wings and Island Grove among them, with over a hundred within a ten-minute drive. For groceries there’s a Walmart at the corner of US-192 and Old Lake Wilson Road under a mile away, a Winn-Dixie at Formosa Gardens Plaza, and Publix, Target and Costco within a short drive. With no shuttle, a hire car is what makes any of this reachable.
For the little onesBabies and toddlers
Windsor Hills is a self-catering community rather than a staffed resort, so parents look after their own children throughout, as at home, at the pools especially. There’s no crèche, kids’ club or childcare of any kind.
For water play with little ones, the splash pad and the separate toddler pool give shallow water away from the bigger slides, and three fenced playgrounds around the community have tunnels and small slides that suit toddlers as well as older children. Baby kit, a cot, high chair, stairgate or car seat, isn’t provided as standard, and whether a given home has any depends on the owner. The usual answer across this part of Kissimmee is a local baby-equipment rental company that delivers a travel cot, high chair, pushchair or stairgate to the door and collects it at the end; several serve the area. The self-catering kitchen is the real advantage with a baby, since you can make up bottles, sterilise and cook plain food rather than eat out every night, and the supermarkets nearby stock nappies, wipes and baby food.
Wherever you stay in Florida, never let a child near standing fresh water on their own, retention ponds, lakes and canals included, since alligators live in fresh water across the state. In the wet season, roughly June to September, the rain tends to come as a short sharp afternoon thunderstorm rather than an all-day washout, which is easy to plan pool time around.
On the resortThings to do
The clubhouse is a 10,000 sq ft building less than a five-minute walk from most of the community, open 8am to 10pm, with the Welcome Center, a fitness centre, a games room, a 48-seat cinema and shower and changing rooms. The games room has arcade games, pool tables, air hockey and table tennis, the cinema shows films in plush seats, and the fitness centre opens from 6:30am.
Outside there’s a sports complex with lit tennis and pickleball courts, a lit sand volleyball court, a lit basketball court, a nine-hole putting green and a barbecue area with charcoal grills and picnic tables. You can borrow equipment, tennis and golf gear, pickleball, basketball and volleyball, table tennis, bean-bag toss and billiards, from the Welcome Center against a small refundable deposit and a small hire fee. Three fenced playgrounds are dotted around the community, with slides, tunnels and a giant outdoor chess set, and the gatehouse is staffed around the clock.
Off the resortThe area and days out
Most families stay here for the parks, a short drive from the gate. How the parks work with young children, tickets, transport and the rest, is covered in our Disney parks section, with the wider Florida practicalities in the Orlando guide. Universal Orlando and SeaWorld are each roughly 20 to 25 minutes away.
Closer to home, the US-192 and Formosa Gardens area has the restaurants and supermarkets already covered. For shopping there’s Rolling Oaks Commons and Sunset Walk a couple of miles away on US-192, Posner Park, an open-air mall, around 15 to 20 minutes off, and the Orlando Vineland Premium Outlets under 20 minutes. Old Town Kissimmee, a strip of rides, shops and a weekly classic-car cruise, makes a family evening out. The nearest hospital is AdventHealth Celebration, minutes away, which has a children’s emergency department.
Loves and gripes
Families rate the pool and the space of a whole home, and flag that upkeep and the walk to the pool vary from one home to the next.
What families love
- The zero-entry lagoon pool, splash pad and water park, a hit with younger children.
- The space of a whole townhouse or house, often with a private pool of your own.
- The games room and cinema in the clubhouse for a rainy or rest day.
- Being close to the Disney parks.
Common gripes
- Standards vary home to home, since each is individually owned and managed.
- The odd private pool reported left dirty or slow to be cleaned.
- The same community listed under several management-company names, confusing to book.
- Homes in the outer parts are a longer walk or short drive from the clubhouse and pool.
- No crèche or childcare, and a hire car is unavoidable.
The gripes follow from the way Windsor Hills is run rather than from the grounds or amenities themselves. Many owners and many management companies mean the standard of any one home varies, and which home you pick decides both how close you are to the pool and what condition a private pool is in when you arrive. It’s why reading a specific home’s recent reviews and confirming what it includes matters more here than the community’s overall name.
Against the newer communities and a Disney hotelHow it compares
Windsor Hills is one of a cluster of gated holiday-home communities along the US-192 and Four Corners corridor southwest of Walt Disney World, alongside the likes of Champions Gate, Storey Lake and Solterra. Its strengths are position and range. It’s one of the closest such communities to the Disney parks, where many newer alternatives sit further out in Davenport or down US-27 with longer drives, and it’s unusual in offering condos, townhouses and full houses inside one gated community, which covers a wider spread of group sizes and budgets than a single-type resort. Being established since 2005, it also has mature landscaping that newer builds lack.
The trade-off is that its shared amenities are more modest than some newer resorts nearby. Storey Lake, built mostly from 2017, and Champions Gate both have larger amenity packages, a lazy river and a bigger resort-style pool at Storey Lake, a similarly large pool and an 18-hole golf course at Champions Gate. Windsor Hills’ pool and water park are well liked but simpler than those. Against a Disney resort hotel, the trade is the usual villa-community one. You give up park transport and a car-free stay for a kitchen, more space and often a private pool, at the cost of driving everywhere and doing your own cooking and cleaning.
The car, the airport and the gateGetting there and around
Fly into Orlando International (MCO), about 30 to 35 minutes’ drive away, and pick up a hire car there, since there’s no airport or theme-park shuttle and a car is the only practical way to reach the resort and get around. Windsor Hills sits just off US-192 with easy access to Interstate 4 for the parks and the wider Orlando area. Sanford airport (SFB) is around an hour away and Tampa (TPA) around an hour and a half.
Inside the gates it’s an ordinary residential street layout, not a golf-buggy or land-train community, so you drive or walk between your home and the clubhouse. Condos and some townhouses are under a five-minute walk from the clubhouse and pool; houses spread further round the community, so the walk varies by which home you book, worth checking the specific home if being close matters. Whoever you book through registers your party with the gatehouse ahead of arrival, generally about a week before, through the Proptia visitor system, so bring a driver’s licence and your booking paperwork showing the address for the gate. There’s a limit of three vehicles per home, and community-wide quiet hours run from 11pm to 7am.
When to goWeather
Windsor Hills sits inland in Central Florida, in the same climate as the rest of the Orlando parks, with hot humid summers and mild drier winters. The pool is heated year-round, so there’s no closed season, and the easiest window with little ones is late February to April and late October to November, cooler and drier and clear of the hottest, wettest months, the same steer as the wider Orlando guide. Hurricane season runs from June to November, and while a direct hit this far inland is rare, a big storm can close attractions for a day or two.
| Month | Daytime high | Overnight low | Rain | Wet days |
|---|---|---|---|---|
| January | 22° | 10.5° | 55 mm | 5 |
| February | 24° | 12.5° | 43 mm | 5 |
| March | 26.5° | 14.5° | 64 mm | 5 |
| April | 29° | 17.5° | 64 mm | 5 |
| May | 31.5° | 20.5° | 98 mm | 7 |
| June | 33° | 23° | 205 mm | 14 |
| July | 33.5° | 24° | 201 mm | 14 |
| August | 33.5° | 24.5° | 206 mm | 15 |
| September | 32° | 23.5° | 185 mm | 12 |
| October | 29.5° | 20° | 70 mm | 6 |
| November | 25.5° | 15.5° | 51 mm | 5 |
| December | 23° | 13° | 55 mm | 5 |
Typical monthly averages from weather-station records.
Questions
How do we actually book a home here?
You book the specific home rather than the resort, through its owner, an Orlando management company or a platform like Airbnb, Vrbo or Booking.com; there’s no central reservations line. Terms are set home by home, so if you want a private pool kept warm in the cooler months, check whether the owner charges to heat it, as many do.
Is this the same as Windsor Island Resort?
No. Windsor Island Resort is a separate community in Davenport, further out and in a different county, and it’s easy to book by mistake because the names and layouts are so alike. The clearest tell is the street: Windsor Hills is on Old Lake Wilson Road in Kissimmee, so check that the home you’re booking says Kissimmee before you pay.
Which type of home is easiest with a pushchair?
A condo. All the condo buildings have a lift and wide doorways, where the townhouses and most houses have stairs. If you want a house on one level, the 4-bedroom single-storey villa is the step-free one, so ask for that layout specifically.
Will our home come with a cot and high chair?
Only if your owner happens to provide them, which many don’t, so ask before you book. If a home doesn’t include them, hiring is straightforward: local Orlando companies deliver baby kit to the door and collect it, so you needn’t fly out with a travel cot.
We have booked a house with a private pool. Is it safe for a toddler?
Not on its own. Treat a private pool as unfenced unless you’ve checked, because the safety features Florida law requires are not the same as a toddler-proof barrier. If you want a removable child fence, ask the owner when you book rather than on arrival, since it’s theirs to supply and not always available.
Do we need a car?
Yes. There is no shuttle, and nothing beyond the gate is walkable, not even the supermarket, so plan on collecting a hire car at the airport and using it for the parks and every meal out.
Is there anything for a baby or a younger toddler?
Yes for free play, no for anything run for you. Little ones have shallow water and fenced playgrounds, but there’s no crèche, kids’ club or scheduled activity of any kind, so nothing is laid on to occupy a toddler while you sit down.
See more Windsor Hills Resort photos
Open the Windsor Hills Resort photo gallery →
Useful links
- Windsor Hills Resort community site: the homeowners’ association site for the clubhouse, pools and gate registration.
- GOV.UK USA travel advice: entry rules, ESTA guidance and safety updates before you travel.
- Florida with little ones: our guide to villas, the parks, hire cars, the ESTA and the Gulf beaches.
- The Disney parks: how Walt Disney World works with young children.
Last updated 30 July 2026.
