Windsor Hills Resort Orlando
About 2 miles from Disney's gates, with a 40-seat cinema and a water park at the clubhouse.
Windsor Hills Resort Vacation Rentals
An established gated villa community in Kissimmee, with condos, townhomes and villas from 3 to 7 bedrooms.
Not sure which villa suits your group in Windsor Hills Resort, Orlando, Florida?
Every enquiry is handled by a single villa specialist. They'll match you to the right property based on your group, dates and priorities.
From first conversation to checkout, the same person stays with you.
- Personalised shortlist (usually 2–3 options)
- Pre-arrival planning & local tips
- 24/7 support during your stay
Where are the villas within Windsor Hills Resort, Orlando, Florida?
There are around a thousand rental homes behind the gates, condos, townhomes and detached villas, all arranged around the central clubhouse and water park. The map shows where each one sits. Planning the rest of the trip? Our Orlando villa holidays guide covers the area.
How many bedrooms do Windsor Hills villas have?
Windsor Hills villas run 3 to 7 bedrooms. A townhome suits two families, and a 6 or 7-bed estate villa gives a big group a private pool and more indoor space than most will use.
Do Windsor Hills Resort villas have a games room?
Most 5-bedroom and larger villas have a games room, with a pool table, football and a console. Smaller villas and townhomes usually don't, so confirm it at enquiry.
Does Windsor Hills have a resort pool and water park?
Yes. A zero-entry lagoon pool, a children's water park with slides and a splash pad sit inside the clubhouse. Collect wristbands at check-in and it's yours for the stay.
Is Windsor Hills Resort gated?
Yes, fully gated with a 24-hour staffed gatehouse. Every guest and vehicle is registered before the barrier lifts, and the streets inside stay quiet enough for children to roam.
How does check-in work at Windsor Hills?
Self check-in throughout. Door codes and access details come through before you fly, and the villa's ready before the group lands.
How far are the theme parks from Windsor Hills?
Disney 5 minutes, SeaWorld 20, ICON Park 20, Universal 25. Close enough that a pool break between two park sessions actually works.
Are there restaurants and supermarkets nearby?
Publix, Walmart and the US-192 restaurants are five minutes from the gate. Most groups do one shop on arrival day and that's it.
How far is Windsor Hills from Orlando airport?
Orlando International (MCO) is 30 to 35 minutes out, pretty much one road the whole way.
What are the key facts about Windsor Hills Resort?
| Feature | Details |
|---|---|
| Distance to Walt Disney World | ~2 miles to the western gate, 5–7 minutes |
| Distance to Universal Studios | ~20 miles, 25 minutes |
| Bedroom options | 3 to 7 bedrooms (condos, townhomes and villas) |
| Pool | Private pool, every villa |
| Clubhouse | Zero-entry lagoon pool, water park, sports courts, 40-seat cinema |
| Games room | Most 5-bedroom and larger villas |
| Check-in | Self check-in, no front-desk queue |
| Security | 24-hour gated community |
| Airport (MCO) | ~25 miles, 30–35 minutes via FL-417 |
| Nearest supermarket | Publix, ~5 minutes on US-192 |
Inside Windsor Hills Resort
Windsor Hills is one of the longest-running and most popular gated resorts near Disney, and it still turns up among the best Orlando resorts. Here's what's actually inside the gates that you must know before booking a villa rental here -
How far is Windsor Hills Resort to Disney?
Properly close. Two miles to Disney's western gate, five to seven minutes, which is about as near as a gated resort gets. Mind you, that two miles is the Animal Kingdom side. Magic Kingdom, EPCOT and Hollywood Studios are more like ten to twenty.
- Two miles to the western gate. Five to seven minutes on a good run.
- Morning park rush? Allow ten to fifteen.
- The other parks, ten to twenty minutes, Magic Kingdom included.
- Near enough to nip back for a pool break mid-day. Few resorts manage that.
- You'll hear the Disney fireworks across the whole resort, and catch them from the west-facing decks. No ticket.
- Get a hire car. Ride-share over a week stings.
Does Windsor Hills Resort have a water park?
Yes, and it's a proper one. There's the big zero-entry lagoon pool, then a separate kids' water park alongside it, both in with every booking.
- The main pool's a big zero-entry, lagoon-style thing. No steps, you just walk in.
- The kids' water park is its own splash-and-slide bit. Jets, bucket dumps, ground sprays. Roughly ages 2 to 12.
- A slide for the bigger ones. A splash pad for the tiddlers.
- Shared hot tub at the clubhouse, open to all.
- Wristbands at check-in and it's all included. No day pass.
- Hours shift by season, and the water park can shut before the main pool, so check on arrival.
What sports facilities does Windsor Hills Resort have?
Plenty, and none of it costs extra. Tennis, basketball, sand volleyball, a putting green and a gym, all on the villa booking.
- Full-size tennis courts. Daylight only, and bring your own kit.
- A basketball court. The teenagers take it over after dark.
- Sand volleyball as well. And a putting green if you fancy a quiet half-hour.
- The gym's got cardio, free weights and the resistance machines. Clubhouse hours, not round the clock.
- Early morning's the time, before it gets too hot.
Does Windsor Hills Resort have a movie theatre?
It does, and it's the thing people remember. A 40-seat cinema in the clubhouse, an actual screening room, which almost no other villa resort has. In with your booking.
- Forty proper cinema seats. Family films on a timetable.
- No ticket, no charge. Part of the clubhouse.
- Brilliant on a rest day, or when a storm wrecks the pool plan.
- Set times, not on-demand, so grab the schedule at check-in.
- Seats are limited. Get there early in peak weeks.
- A few of the bigger villas have their own cinema too, if you'd sooner stay in.
What's included with the Windsor Hills clubhouse?
Pretty much everything with your villa booking, and it's all in the price. No daily fee, no signing up at a desk. Only a few bits cost extra.
- In: the lagoon pool, water park, hot tub, the courts, putting green, gym, the 40-seat cinema, arcade, billiards, the playgrounds.
- There's a castle-style playground the kids bolt straight for.
- The Marketplace and Grill, middle of the clubhouse, does food and drink. That bit's paid.
- A little shop for odds and ends. Publix is five minutes for a proper shop.
- Arcade's free to walk into. The machines take coin or card.
- What you'll pay for: poolside food, kit hire, the odd activity.
What size villas does Windsor Hills have?
Anywhere from 3 to 7 bedrooms, and across three types: condos, townhomes and proper detached homes. The 4 and 5-beds get booked the most.
- A 3-bed sleeps six, with its own pool. Townhome versions get a splash pool.
- The 4-bed's the workhorse. Sleeps eight, good value for a standard group.
- 5-beds for the bigger families, and a games room's common at that size.
- 6 and 7-beds take two families or a multi-gen lot. Four or five bathrooms, a bigger deck.
- It's a sizeable resort, mind: roughly 320 condos, 210 townhomes, 469 homes behind the gates.
- Floor plans differ owner to owner, so the 5 Star Villa Holidays team runs you through the specifics first.
For the very largest, see our Orlando estate mansions. Prefer something off-resort? Browse private homes to rent in Orlando.
Do Windsor Hills villas have a heated pool?
Every villa's got its own pool. Heating, though, is a paid extra, and it really only earns its keep October to March.
- The private pool's standard. Size depends on the place.
- Heating's a chargeable add-on, per night or a flat fee, depends on the management company.
- Roughly $40 to $65 a night. Pin it down at booking.
- October to March, an unheated pool drops to 65–70°F, so it's worth it.
- Summer? Don't bother. The sun sorts it.
- Townhome splash pools heat quicker, and the price can differ, so check that on its own.
Do Windsor Hills villas have a hot tub?
Two ways here. Some villas have a private jacuzzi on the deck, and there's a shared one at the clubhouse for everyone else.
- A private jacuzzi's on select villas only, out on the pool deck.
- Good for the grown-ups, a quieter soak after a park day.
- The communal hot tub at the clubhouse is open to all.
- Heating's usually in the rate, but confirm at booking.
- The private-spa villas go early in peak season, so shout early.
- Mention it when you enquire and we'll check the setup before we recommend.
Do Windsor Hills villas have private games room?
Lots do, not all. It comes down to the owner, and it's the 5-bed-and-up villas where you'll usually find one.
- Most 5-beds and bigger have one. The 3-beds and townhomes, rarely.
- Usual kit: pool table, foosball, air hockey, big screen, a console.
- Two 5-beds can feel worlds apart, one done up with a proper games room and a west-facing deck, another tired. A filter won't tell you that, so we check first.
- Some throw in themed bedrooms or a private cinema.
- The clubhouse arcade's there too, coin-operated, open to all.
Is Windsor Hills good for large groups?
It works for a big group. Villas to 7 bedrooms, sleeping around 14, and a clubhouse that gives everyone somewhere to be off the villa.
- The 6 and 7-beds sleep twelve to fourteen in one house, own pool included.
- Villas next door to each other are sometimes doable for bigger parties. Needs planning early, and no promises.
- Every villa's got its own pool, so there's space apart from the clubhouse.
- The clubhouse, pool, water park, courts, cinema, that's the shared bit.
- Fancy a meal in? The 5 Star Villa Holidays team can line up a private chef.
- Peak-season big villas go nine to twelve months out. Book early.
Need more than one property? Browse our wider Orlando vacation rental collection. Still weighing resorts? Windsor Hills sits among Orlando's most sought-after resorts in our guide.
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