Windsor Hills Villas in Florida 2026 & 2027
For water thrills, all-day entertainment, and on-site dining and sports facilities, Windsor Hills Resort in Orlando is where you’ll want to stay. Secure and safe, this 24/7 gated community is also one of the closest villa communities to Walt Disney World Resort, just 3 miles away. Families of all sizes can find a home that fits. Groups of up to 6 will love the 3-bedroom condos near the clubhouse and resort pool, while families of up to 8 can enjoy 3-bedroom townhomes with a private splash pool for extra downtime fun. Larger families of up to 12 can spread out in the spacious 4- to 6-bedroom villas, each with a private swimming pool. So no matter your travel style, party size, or budget, Windsor Hills Resort Orlando offers a convenient home base for your family holiday.
For water thrills, all-day entertainment, and on-site dining and sports facilities, Windsor Hills Resort in Orlando is where you’ll want to stay. Secure and safe, this 24/7 gated community is also one of the closest villa communities to Walt Disney World Resort, just 3 miles away. Families of all sizes can find a home that fits. Groups of up to 6 will love the 3-bedroom condos near the clubhouse and resort pool, while families of up to 8 can enjoy 3-bedroom townhomes with a private splash pool for extra downtime fun. Larger families of up to 12 can spread out in the spacious 4- to 6-bedroom villas, each with a private swimming pool. So no matter your travel style, party size, or budget, Windsor Hills Resort Orlando offers a convenient home base for your family holiday.
- Family-friendly resort packed with top-notch amenities
- All-ages fun with a waterpark, movie theatre, and sports courts
- Just 3 miles from Walt Disney World
Windsor Hills Resort Villas
Kissimmee, Windsor Hills - 3-bedroom town house
- Private splash pool
- Close to Disney
8 Guests 
3 Bedrooms 
3 Bathrooms
Kissimmee, Windsor Hills - 3-bedroom condo
- TV's in every bedroom
- Close to Disney
- 6 Guests
- 3 Bedrooms
- 2 Bathrooms
Kissimmee, Windsor Hills - 3-bedroom condo
- Themed kids’ bedroom
- Close to Disney
- 6 Guests
- 3 Bedrooms
- 2 Bathrooms
Windsor Hills Resort Facilities
-
Children's Pool -
Cinema Room -
Close to Disney (under 10 miles) -
Close to shops -
Clubhouse -
Fitness Centre -
Games Room/Arcade -
Gated Community -
Kid's Playground -
Mini Market -
Resort Pool -
Restaurant onsite -
Sports Facilities -
Tennis Courts -
Water Park
Windsor Hills Resort Location
You’ll love Windsor Hill Resort’s ideal location – just 3 miles from Walt Disney World Resort. Situated on North Old Lake Wilson Road, the Most Magical Place on Earth is a 10-minute drive away, plus you’re close to other world-class attractions and thrilling theme parks.
-
Airport:- Orlando International Airport (24 miles)
- Tampa International Airport (72 miles)
Flight Times- 9 hours from London (Approximately)
Transfer Time- 32 mins by car from Orlando International Airport
Time Difference:- GMT -5 hours
- Walt Disney World Resort (9 miles)
- Universal Orlando Resort (16 miles)
- SeaWorld Orlando (14 miles)
- International Drive (11 miles)
- Legoland Florida Resort (30 miles)
- Peppa Pig Theme Park Florida (33 miles)
- Busch Gardens Tampa Bay (65 miles)
- Clearwater Beach (89 miles)
- Children's Pool
- Cinema Room
- Close to Disney (under 10 miles)
- Close to shops
- Clubhouse
- Fitness Centre
- Games Room/Arcade
- Gated Community
- Kid's Playground
- Mini Market
- Resort Pool
- Restaurant onsite
- Sports Facilities
- Tennis Courts
- Water Park
Amenities in Windsor Hills
From action-packed days to laid-back moments by your own private pool, Windsor Hills Resort makes it easy to do as much - or as little - as you like. Start your morning with a dip in the zero-entry resort pool, add a splash of excitement on the water slides, challenge the family in the games room, then wind down at the movie theatre. With a children’s playground, sports courts, and a daily schedule of activities, every day brings a new way to make holiday memories.
Cinema Room
For a perfect movie night without leaving the resort, settle into Windsor Hills’ high-definition movie theatre. With seating for 48 guests in plush, comfortable chairs and three showtimes daily, it’s easy to fit a film into your plans. The weekly schedule features everything from timeless classics like The Wizard of Oz to Disney favourites like Frozen and Encanto, as well as recent hits like Dune: Part Two.
Water Park
Whether you’re looking to cool down or have thrilling water fun, the Windsor Hills water park has something for everyone. Adventure lovers can race down the two large duelling water slides, while younger guests enjoy their own fun on the smaller slides and at the giant splash pad. Meanwhile, the heated and zero-entry lagoon pool invites you to soak up the sunshine all day long. When it’s time to truly unwind, slip into the 10-person hot tub and let the relaxation begin.
Games Room/Arcade
Feeling competitive, or just in the mood for some light-hearted fun? Head to the Windsor Hills games room. Line up a shot at the pool table, face off at air hockey, sharpen your skills at ping pong, or enjoy a variety of modern arcade games. Open from morning to night, it’s a favourite hangout for all ages and an especially great spot for keeping the fun going on rainy days.
Windsor Hills Leisure
Sports Facilities
For those who like to stay active, Windsor Hills offers plenty of ways to play. Enjoy a friendly match of tennis, volleyball, basketball, or pickleball, all open daily for your enjoyment. There’s even a putting green where you can practise your golf swing. And if you’ve left your sports gear at home, the Welcome Centre has everything you need to join in the fun.
For those who like to stay active, Windsor Hills offers plenty of ways to play. Enjoy a friendly match of tennis, volleyball, basketball, or pickleball, all open daily for your enjoyment. There’s even a putting green where you can practise your golf swing. And if you’ve left your sports gear at...
For those who like to stay active, Windsor Hills offers plenty of ways to play. Enjoy a friendly match of tennis, volleyball, basketball, or pickleball, all open daily for your enjoyment. There’s even a putting green where you can practise your golf swing. And if you’ve left your sports gear at home, the Welcome Centre has everything you need to join in the fun.
Clubhouse Events
Alongside the resort’s facilities, Windsor Hills runs a full schedule of daily activities for all ages. Children can enjoy hands-on fun such as sand art, glitter tattoos, Lego building, and mini-robots, while adults can join in with events like Wine Wednesday, ceramics, paint-and-sip sessions, and mosaic coaster-making. Activities change weekly, so be sure to check the schedule during your stay.
Alongside the resort’s facilities, Windsor Hills runs a full schedule of daily activities for all ages. Children can enjoy hands-on fun such as sand art, glitter tattoos, Lego building, and mini-robots, while adults can join in with events like Wine Wednesday, ceramics, paint-and-sip sessions, and...
Alongside the resort’s facilities, Windsor Hills runs a full schedule of daily activities for all ages. Children can enjoy hands-on fun such as sand art, glitter tattoos, Lego building, and mini-robots, while adults can join in with events like Wine Wednesday, ceramics, paint-and-sip sessions, and mosaic coaster-making. Activities change weekly, so be sure to check the schedule during your stay.
The Marketplace & Grill
The Marketplace & Grill is your go-to for easy holiday convenience. Pick up made-to-order favourites like burgers and sandwiches, stock up on groceries and drinks, or grab pool essentials such as sunscreen, hats, and toys. Open daily, it also offers online ordering with pickup or delivery for nights when you’d rather relax than cook.
The Marketplace & Grill is your go-to for easy holiday convenience. Pick up made-to-order favourites like burgers and sandwiches, stock up on groceries and drinks, or grab pool essentials such as sunscreen, hats, and toys. Open daily, it also offers online ordering with pickup or delivery for...
The Marketplace & Grill is your go-to for easy holiday convenience. Pick up made-to-order favourites like burgers and sandwiches, stock up on groceries and drinks, or grab pool essentials such as sunscreen, hats, and toys. Open daily, it also offers online ordering with pickup or delivery for nights when you’d rather relax than cook.
Florida 24/7 Support Team
- Friendly and helpful Florida team of locals
- Available 24/7 to assist Ocean Florida holidaymakers
- Providing expert knowledge on Florida's attractions, dining scene, and entertainment
To ensure your holiday runs smoothly, we have a team based in Florida ready to offer their assistance. You can reach them by phone or email 24 hours a day, 7 days a week, to get recommendations and helpful advice during your stay in the Sunshine State.
To ensure your holiday runs smoothly, we have a team based in Florida ready to offer their assistance. You can reach them by phone or email 24 hours a day, 7 days a week, to get recommendations and helpful advice during your stay in the Sunshine State.
To ensure your holiday runs smoothly, we have a team based in Florida ready to offer their assistance. You can reach them by phone or email 24 hours a day, 7 days a week, to get recommendations and helpful advice during your stay in the Sunshine State.
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Windsor Hills FAQ's
Windsor Hills FAQ's
Windsor Hills FAQ's
Windsor Hills Resort is situated in the Orlando area, specifically in Kissimmee, and it couldn’t be more conveniently located. Just off North Old Lake Wilson Road and close to U.S. Highway 192, it’s one of the closest villa communities to Disney World - only 4 miles away - while Universal Orlando Resort is also within easy reach at around 16 miles. With Disney, Universal, and so many other attractions nearby, it’s no wonder Windsor Hills Resort is a favourite for families looking to make the most of their Orlando holiday.
Honestly, there’s almost too much to list. One of Windsor Hills Resort’s main priorities is to keep the whole family entertained. You’ve got a zero-entry swimming pool perfect for little ones, a water park with two duelling slides, and a splash pad for even more water fun. Both kids and adults will love the on-site movie theatre, games room, and sports courts, including tennis, basketball, volleyball, and even pickleball. If you fancy something a little more relaxed, hit the putting green, lounge in the clubhouse, or order a meal at the Marketplace & Grill. Daily clubhouse events keep the fun going, and there’s something for everyone, from playgrounds for kids to a fitness centre for adults.
Windsor Hills Resort is just four miles from Disney World, allowing you to get to the Happiest Place on Earth in just a 10-minute drive. That makes Windsor Hills Resort one of the closest villa communities to Disney and the journey there should be as stress free as your time exploring the parks.
The simplest route will take you via Old Lake Wilson Road and US-192 east. Along the way, just follow signs for whichever park you have your sights set on and voila! You’ll be there in no time. While car rental is the best option for making the most of your freedom on your Florida holiday, we understand that driving abroad may not be to everyone’s taste. If you prefer not to have to be the family chauffeur, your next best bet would be ride sharing services such as Uber and Lyft. At just 10 minutes away, this short trip certainly won’t break the bank and will allow for total peace of mind.
Unfortunately, at this point in time, Windsor Hills Resort has no shuttle bus to the parks. However, it’s always best to check the resort website in case of any changes. As there is no shuttle service available currently, car hire is a great option to allow you the freedom to get to Disney in your own time. And here at Ocean Florida, we can help you get set up.
We offer a range of car hire package options to suit your needs. Plus, all our car hire packages come with fully comprehensive insurance, meaning that’s one less thing to worry about. Having your own transport not only allows you easier access to Disney but you can also tick off all of Orlando’s best theme parks. SeaWorld, Universal Resort, and Legoland Florida are all under 30 miles from Windsor Hills. All that’s left to do is pick the perfect road trip song playlist and hit the open road.
Windsor Hills is just about 16 miles from Universal Orlando Resort. On a typical day, you can expect the drive to take around 25 minutes, though it may take a bit longer during peak traffic, especially on the I-4. The route is straightforward: take Old Lake Wilson Road to US-192 east, merge onto I-4 east, and follow the signs to Exit 75A for Universal Boulevard. From there, it’s easy to reach Universal’s parking and guest drop-off areas.
Windsor Hills is roughly 24 miles from Orlando International Airport. After landing, the easiest route is FL-528 west onto I-4 west, then take Exit 64 onto US-192 west, and finally a left onto North Old Lake Wilson Road. You’ll be unpacking and relaxing at your villa before you know it.
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