Windsor Hills Resort Villas
Located just minutes away from Walt Disney World, our Windsor Hills villas and resort rentals are perfect for magical family vacations in Orlando.
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Windsor Hills Villas and Resort Rentals
Located just moments away from Disney World, Windsor Hills Resort is the closest and most convenient Orlando resort for family vacations to the theme parks. Our stunning Windsor Hills villas and resort rentals are ideal for families or large groups, with space for up to 17 guests, plus all the amenities you could wish for.
One of Orlando’s premier gated resorts, Windsor Hills is a beautiful spot for a vacation and is as close to Disney World as you can get without physically being there. The resort is about 5 minutes drive from Disney and is situated close to Highway 192, making it ideal for exploring all of Orlando’s attractions. Windsor Hills also has fantastic amenities for guests of the resort, including health and fitness facilities and family activities.
With a fabulous selection of Windsor Hills villas and rentals for vacations in Orlando, you can book a fantastic stay with us. Perfect for families or large groups, our Windsor Hills villas have excellent features and facilities, as well as access to all of the resort’s amenities.
Popular Resort Villas
The best time to visit Windsor Hills Resort Orlando is March to May and September to November, when the weather is warm, crowds are lighter, and theme park wait times are generally shorter.
Orlando is busy year-round, but school holidays and festive periods are the peak times, bringing larger crowds and higher demand. If your schedule allows, visiting outside these windows offers a more relaxed experience. Winter is also an excellent option, with pleasant temperatures and plenty of sunshine, making it ideal for enjoying the resort’s outdoor amenities and nearby attractions without the intensity of summer crowds.
Yes, you can park one car in front of your vacation rental at Windsor Hills, with extra parking areas around the resort if you have more than one vehicle.
When you check in, you’ll be able to get a wristband that will allow you to access the pool and water park. Make sure you keep the wristband on for your entire stay or attach it somewhere safe and visible such as a hat, bag, or shoe. To get your wristband, head over to the Welcome Center at the Clubhouse.
Yes, the condo blocks all have elevators.
Universal Studios is 15.7 miles from Windsor Hills Resort, with an approximate drive time of around 25 minutes.
The address for Windsor Hills Resort is: 2600 Old Lake Wilson Road, Kissimmee, Florida 34747.
Windsor Hills Resort enjoys a convenient location close to Orlando’s major airports, making arrival simple for both domestic and international travellers. Whether you’re hiring a car or arranging private transportation, reaching the resort is smooth and stress-free.
From Orlando International Airport (MCO)
Orlando International Airport (MCO) is the most popular arrival point, located approximately 25 miles from Windsor Hills Resort, with an average drive time of 35-40 minutes, depending on traffic. MCO offers nonstop flights from major cities across the US, the UK, and Europe.
Once you land, you’ll find all major car hire companies conveniently located at the airport terminals, along with taxis and ride-share services. The most direct routes typically use FL-417 or FL-528, connecting easily to I-4 and local roads leading to the resort.
From Orlando Sanford International Airport (SFB)
Orlando Sanford International Airport (SFB) is a quieter alternative, often used by low-cost and select domestic carriers. It sits around 55 miles from Windsor Hills Resort, with a drive time of approximately 1 hour to 1 hour 10 minutes via I-4.
While slightly further away than MCO, Sanford can be a good option for travellers prioritising flight availability or value.
Private Car Hire & Transportation
For a seamless start to your vacation, our Concierge team can arrange private airport transfers, chauffeur-driven services, or pre-booked car hire delivered directly to your Windsor Hills vacation home.
If you're driving or looking to hire a car for your stay at Windsor Hills Resort, it's easily accessible from major highways.
The resort provides secure and gated access for guests, and once inside, you'll find well-maintained roads and clear signage to guide you to your accommodation.
Windsor Hills Resort is conveniently located near Walt Disney World in Orlando, Florida. There are several transportation options to get from the resort to Disney World:
Rental Car: Renting a car is a popular option for visitors who want the flexibility to explore other attractions in the area. There are several car rental agencies available in Orlando.
Taxi or Ride-Sharing: Taxis and ride-sharing services like Uber and Lyft are readily available in the area and can take you directly to Disney World.
Public Transportation: Lynx, the local public transportation system, operates buses that connect the area to Disney World. However, this option may be less convenient and time-consuming compared to other modes of transportation.
There is no official Windsor Hills Resort shuttle to Disney. However, private shuttle companies run daily services, and private ride services such as Uber and Lyft are available from the resort.
Distances from Windsor Hills Resort
| Attraction | Distance from Windsor Resort (miles) | Drivetime to attraction (mins) |
|---|---|---|
| Magic Kingdom | 10.5 | 22 |
| Epcot | 7.2 | 21 |
| Animal Kingdom | 9.5 | 22 |
| Disney Springs | 9.4 | 21 |
| Universal Studios | 15.7 | 25 |
| Legoland | 32.4 | 50 |
| Convention Center | 12.2 | 21 |
| Gatorland | 15.6 | 25 |
| International Drive | 14.5 | 25 |
What's on Resort?
Windsor Hills Resort offers a wide range of amenities designed to make your stay unforgettable. Start your day with a refreshing swim in the resort's lagoon-style pool, complete with a water slide and hot tub. The pool area is surrounded by lush tropical landscaping, creating a serene and relaxing atmosphere. Windsor Hills Orlando pool hours are generally 8am through 10pm.
For those looking to stay active, the resort features a fitness center, tennis courts, and a basketball court. Enjoy a friendly game with your family or challenge your friends to some friendly competition. There is also a putting green for golf enthusiasts to practice their swing.
The resort's clubhouse is the hub of entertainment and leisure activities. Inside, you'll find a movie theater where you can catch a film or enjoy a family movie night. There is also a games' room with arcade games, pool tables, and a ping pong table, ensuring there's something for everyone to enjoy.
If you prefer outdoor activities, take advantage of the resort's playgrounds and picnic areas. Let the kids run around and have fun on the playground while you relax and enjoy a picnic in the beautiful surroundings.
Windsor Hills Resort also offers convenient amenities such as a sundry shop, where you can find essential items and snacks, and a 24-hour gated entrance for added security and peace of mind.
Things to do nearby
Disney, Universal and other attractions
Windsor Hills vacation rentals are particularly popular because they are so close to Disney World (2-4 miles), Universal Studios (14-16 miles), and other Orlando theme parks. Spend the day with Mickey Mouse, enjoy some movie magic at Universal Studios or head a little further afield for fun at Legoland (30-31 miles) before returning to the peace and comfort of your Windsor Hills Resort vacation home.
Treetop climbing
If you’ve got a head for heights, why not test your mettle at Orlando Tree Trek Adventure Park, just 2.5 miles away? Suitable for kids, teens and adults, with treetop courses consisting of zip lines, rope elements, and obstacles. Orlando Tree Trek Adventure Park is open all year round and is located in Kissimmee, just a 6-minute drive from Windsor Hills Resort.
Golf
Florida is renowned for spectacular golfing, with the mild climate providing year-round opportunities to practice your swing. Windsor Hills Resort has many golf clubs nearby, including Mystic Dunes Golf Club (1.8 - 2 miles away), one of the best courses in Florida. It has courses designed by PGA professional Gary Koch and is a must-play for golf enthusiasts.
Sightseeing
Also nearby is the cute town of Celebration, under 6 miles away. If you think that it looks like something straight out of a classic Disney movie, that’s no coincidence, because Celebration was designed by the Walt Disney Company in the 1990s. If you’re there around the holidays, Celebration puts on a stunning Christmas event that draws people back year after year and is well worth a visit.
Seafood & American - $$ - 5690 W Irlo Bronson Memorial Hwy, Kissimmee, FL 34746.
Red Lobster is a popular seafood restaurant chain known for its fresh seafood dishes, including lobster, shrimp, crab, and various other seafood options. They also offer a variety of non-seafood items, making it a great dining option for groups with different preferences.
American & Bar Grill - $$ - 5034 W Irlo Bronson Memorial Hwy, Kissimmee, FL 34746.
At TGI Fridays, you can expect a diverse menu featuring classic American dishes, including burgers, steaks, ribs, chicken, seafood, and a variety of appetizers and desserts. They also offer a selection of cocktails, beers, and other beverages for guests to enjoy.
Pizza & Italian - $$ - 7866 W Irlo Bronson Memorial Hwy, Kissimmee, FL 34747.
The Kissimmee location of Giordano's offers a diverse menu featuring an array of deep-dish and thin-crust pizzas, appetizers, salads, sandwiches, and desserts. Their signature stuffed deep-dish pizza is a must-try, with layers of cheese, toppings, and tomato sauce, all encased in a buttery, flaky crust.
Japanese Steakhouse - $$$ - 2901 Parkway Blvd, Kissimmee, FL 34747.
Take Japanese offers a variety of traditional Japanese cuisine, including sushi, sashimi, tempura, teriyaki, and more. The restaurant provides a casual and relaxed dining atmosphere, making it a popular choice for locals and tourists alike.
American & Sports Bar - $$ - 7700 Westgate Blvd, Kissimmee, FL 34747.
Drafts Sports Bar and Grill serves a diverse menu featuring classic American fare, including burgers, sandwiches, salads, and appetizers. They also have a wide selection of draft beers, cocktails, and non-alcoholic beverages to complement your meal.
The restaurant is known for its multiple large-screen TVs, making it an ideal spot to catch live sports events and games. This adds to the lively ambiance, creating a fun and social dining experience for families, friends, and sports enthusiasts.
Family Restaurant & Diner - $$ - 5170 W Irlo Bronson Memorial Hwy, Kissimmee, FL 34746.
Perkins is a family-friendly restaurant known for its delicious breakfast, lunch, and dinner options. They serve a wide variety of American comfort food, including pancakes, omelets, sandwiches, burgers, and pies.
Dinner Theater & Entertainment - $$$$ - 4510 W Vine St, Kissimmee, FL 34746.
Medieval Times is a popular dinner and entertainment attraction located near Windsor Hills Resort in Orlando, Florida. The venue offers a unique and immersive experience that takes guests back in time to the age of chivalry and knights. Upon arrival, guests are assigned a specific section of the castle, each representing a different knight and color. They are then treated to a medieval feast, which includes a hearty meal served in traditional style, with no utensils, just like in the Middle Ages.
During the dinner, guests are entertained by a thrilling show featuring knights, jousting tournaments, sword fights, and equestrian performances. The knights compete in various challenges, and guests can cheer on their assigned knight in hopes of seeing them emerge as the champion.
Olympic-size resort Swimming poolThe focal point of the resort. Open daily, the resort pool is a great place to cool off in the Florida sunshine. During the winter months, the pool is heated to 82 degrees Fahrenheit.
Water ParkThis water park is a firm favorite with families. With multiple waterslides, splash pads, and pools. The water park is open daily, year-round (weather permitting).
Children's play areaWith slides, roundabouts, swings, and even a miniature castle to explore, there are enough attractions on offer to amuse and delight throughout your entire vacation.
Golf putting greenFlorida is renowned for its world-class golf courses. Visit the putting green where you can get in some practice before heading to one of the nearby courses.
Sports & recreationFrom tennis courts, a putting green and sand volleyball, to pickleball, basketball, ping pong and timeless cornhole, Windsor Hills offers a sporty distraction for all ages.
ClubhouseWindsor Hill’s clubhouse is the place to go if you have any requests or queries about the resort amenities. It is located right in the heart of Windsor Hills, and is open daily, year-round.
Fitness centerYour gym schedule doesn’t need to drop off because you’re on vacation, as Windsor Hills Resort has got a well-appointed fitness center for guests’ use. Open daily, there's no excuse!
Games roomFor those rare rainy days in Orlando, Windsor Hills Resort has got a fantastic games room, complete with video games, billiards, and table tennis to keep the whole family entertained.
ShopWhether you’re grabbing a snack or stocking up on supplies for your vacation rental kitchen, Windsor Hill’s onsite grocery store is a handy place to pick up supplies.
Movie theatreCatch the latest blockbuster or classic favorites at Windsor Hill Resort’s all-weather movie theatre. Equipped with cinema seating and surround-sound all you need do is bring the popcorn!
Windsor Hills vacation homes with Concierge
Here at Top Villas, we offer Windsor Hills vacation home rentals that are more than just a place to stay; we also have a range of Concierge Services to enhance your vacation experience. When you book your vacation home, you can take advantage of our amazing optional services and effortlessly create your perfect getaway.
From optional add-ons such as grocery delivery services, to private chefs, and baby gear rentals, including cribs, high chairs, and strollers, our Travel Planners can arrange whatever you need for a seamless vacation experience.
Windsor Hills rentals with pools
Enjoy a refreshing dip in your own private pool at our Windsor Hills vacation rentals. The villas have lanai-covered areas with swimming pools and hot tubs, meaning that you can make the most of this fun facility even when the sun isn’t shining.
You'll also find sun loungers, tables, chairs and optional BBQs set up around the pool, enabling you to catch some rays while keeping an eye on the kids in the water.
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Windsor Hills vacation rentals with themed bedrooms
From pirates to princesses, superheroes to space and everything in between, our Windsor Hills vacation rentals with themed bedrooms are ideal for stoking the imagination.
With spectacular features such as whimsical castle beds, wizard bunkbeds, and dino-discovery dens, these awesome themed rooms are sure to be the talk of your vacation and provide many happy memories to take home with you. Elevate your kids' stay further, with our optional surprise character meets, themed goodie bags, themed party decorations and more!
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Windsor Hills Orlando condos
Windsor Hills Orlando Condos offer a fantastic accommodation option for travelers seeking a comfortable and convenient stay near the area's top attractions. These condos provide spacious and well-appointed living spaces with multiple bedrooms, allowing families and groups to stay together and enjoy a home-away-from-home experience.
The condos at Windsor Hills are fully furnished and equipped with modern amenities, including a full kitchen, living area, and private bathrooms. You'll have everything you need to relax and unwind after a day of exploring the theme parks or shopping in Orlando.
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