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Windsor Hills Resort Vacation Rentals

Browse 115 of the best Windsor Hills Resort villas, condos and townhouses, from $104 per night

#1 in Windsor Hills Resort

Top Villas is Windsor Hills Resort's #1 vacation rental company, offering the best range of 2 to 7 bedroom homes

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Choose from carefully selected vacation homes in Windsor Hills Resort

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About our Windsor Hills Resort vacation homes

Looking for a vacation rental in Windsor Hills, Orlando? From spacious 2-bedroom condos to large 6-bedroom villas, we offer dozens of comfortable modern rentals to suit all tastes and budgets. Our villas in Windsor Hills offer amazing amenities such as private pools, hot tubs, game rooms and home theaters. Some even have beautiful themed bedrooms, perfect for little ones. What's more, all of our rentals are ideally located just minutes from Disney World. Not only is Windsor Hills home to a range of fantastic villas, it's also packed with lots of fun things to do. You can laze the days away by the huge resort pool, sip cocktails from the Tiki bar or watch movies at the family cinema. Golfers will love the on-site putting green, and sports buffs can work up a sweat at the tennis, sand and volleyball courts.

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Luxury villas in Windsor Hills Resort

Windsor Hills is a popular vacation community located in the heart of Kissimmee, Orlando. A private, gated resort, it offers a wide range of accommodation including townhomes that range in size from 2–3 bedrooms (all with a private splash pool) and villas with 4, 5 and 6 bedroom options, all with large private pools. The resort itself features a fantastic water park, along with a raft of other amazing leisure facilities to keep the whole family entertained.

Where is Windsor Hills Resort?

This resort is located in the beautiful area of Kissimmee, Orlando. Kissimmee is one of the largest regions in Orlando and is home to all of the Disney theme parks. Located just off Highway 192 along Old Lake Wilson Road, you’ll enjoy easy access to Interstate 4 which runs right through Orlando. Close by are several supermarkets including Publix and Walmart.

How far is Windsor Hills from Disney?

Windsor Hills Resort is one of the closest Orlando resorts to Disney World and even offers a quick back road to Animal Kingdom that is just a few minutes’ drive from the actual gate. Magic Kingdom is a little further away, however if you are looking for a vacation rental community that is close to Disney, this is the perfect choice.

Driving distances

Point of interest

Distance (miles)

Disney World


Disney Springs


Universal Studios






Downtown Orlando


Sunset Walk (Margaritaville)


International Drive


Orlando International


Premium Outlets (Vineland)


Publix Supermarket


Mystic Dunes Golf Club


Getting to Windsor Hills from Orlando Airport (MCO)

Windsor Hills is situated just 23 miles from Orlando International Airport and is a very easy drive via the 528 and I-4. Choose to book a rent-a-car that you can collect directly from the terminal, or let us arrange a private transfer directly to your villa. A popular choice is our car-on-the-drive service whereby we collect you from the airport, drive you to your villa and have your rent-a-car waiting for you on the drive.

All transport can be arranged for you by your dedicated guest experience manager who is assigned to you immediately after you book with Top Villas. For more extra services please take a look at our travel extras.

Things to do near Windsor Hills Resort

You could easily spend your vacation enjoying the amenities on-site, however if you want to venture out you’re in the perfect position to take advantage of everything Orlando has to offer.

Spend exciting days exploring the many incredible theme parks and water parks, see alligators up close at Gatorland, or head into Downtown Orlando to get your culture fix. Universal Studios, Seaworld and Legoland are all within easy reach, as is the buzzing Highway 192 area and Old Town Kissimmee.

There are myriad restaurants nearby including popular spots like Outback Steakhouse, TGI Fridays, Cracker Barrel, Chili’s, Thai Thani, Rock & Brews, plus many more. In addition, you’ll find myriad amazing restaurants at Disney World, Disney Springs, Sunset Walk (Margaritaville) and Old Town Kissimmee.

From Windsor Hills, you’ll enjoy easy access to Orlando’s best shopping malls such as the Premium Outlets, Florida Mall, the Mall at Millenia, and Pointe Orlando. You’ll also find great shopping at the Promenade at Sunset Walk, Disney Springs and Old Town Kissimmee.

If you’re looking for great golf you’ll find the popular Mystic Dunes Golf club close by. Highlands Reserve, Southern Dunes, Celebration Golf Club, Champions Gate, and the Disney golf courses are also within easy reach.

For stocking up, the closest grocery stores to Windsor Hills are Publix and Super Target, located west on 192 at the 492 toll road crossover. You’ll also find a Super Walmart around 10 minutes from the resort, plus the Marketplace store located onsite.

Other things to do nearby

Take a trip to Celebration, the town Disney created, located just a few miles away. Full of charming homes and a wonderful town center full of great restaurants, an ice cream parlour, bars, coffee shops and a beautiful chain of lakes with a walking trail. You can grab an ice cream and enjoy a gentle stroll around the lakes.

Also located just minutes away is the entertainment district Sunset Walk at Margaritaville. Here you will find stunning water park H2O Live, plus several incredible restaurants, a movie grill cinema, several shops and many bars. It’s a fun place to hang out!

What to do at Windsor Hills Resort

Windsor Hills was one of the first resort communities that catered for vacationers in the Disney area. Recently it has completely renovated its water park and has now introduced brand new slides and improved all the facilities on site.

Amenities include:

  • Huge resort-style pool
  • Waterpark with slides and water attractions
  • Hot tub
  • Clubhouse with billiards and gaming arcade
  • Restaurant & bar
  • 40-seat cinema
  • Sports courts
  • Putting green
  • Picnic and BBQ area
  • Castle-themed playground
  • Fitness center
  • 24-hour security
  • Shuttle bus service to all the parks and shops (fees apply)
  • DVD rental and ATM
  • RV and boat parking available

Kids’ activities at Windsor Hills Resort

When going on vacation it’s important to know the kids will be entertained. Book a stay at Windsor Hills and you can rest assured the children will have plenty to do. Everything is included with your stay so you and your entire group will have full and unlimited access to everything at the resort including use of the basketball, tennis courts, volleyball courts, putting green and onsite movie theater.

Other amenities at Windsor Hills Orlando

The huge resort-style pool is sure to please guests of all ages. This double olympic-sized lagoon features crystal clear water and an easy beach entry. The brand new water park packs in a lot more fun including the dueling water slides, as well as two smaller slides perfect for younger children.

There’s also a state-of-the-art fitness center located inside the clubhouse as well as the fantastic Market Place Grill restaurant.

When to visit Windsor Hills Resort

No matter what time of year you visit Orlando, there is always something exciting going on. Even during the cooler months as the main pool at Windsor Hills is heated. The most popular times to visit Orlando are during the holidays including Easter, Passover, Thanksgiving, Christmas and New Year. Prices will tend to be higher during these dates.

For the lowest rates look out for last-minute deals (join our mailing list to be the first to know!) and special offers during the low season (school term time) when the weather in Florida is often reliably sunny.

Windsor Hills rentals

Tempted to book a stay at Windsor Hills? We offer a wide range of Windsor Hills rentals with full access to all resort amenities. Ranging in size from 2-6 bedrooms, these homes come complete with a private pool. Our larger homes also offer games rooms, home theaters and themed kids’ bedrooms.

10 of the best vacation homes at Windsor Hills Resort

Windsor Hills Resort 437

Windsor Hills Resort 604

Windsor Hills Resort 602

Windsor Hills Resort 603

Windsor Hills Resort 309

Windsor Hills Resort 510

Windsor Hills Resort 302

Windsor Hills Resort 254

Windsor Hills Resort 76

Windsor Hills Resort 426

What is included in my stay at Windsor Hills?

The quick answer is everything. Top Villas makes staying in a vacation home feel like home - just pack your bags and turn up at your new home from home! Before check in we will provide you with a door code meaning you do not have to go anywhere or meet anyone to get keys. All towels, linens and utensils are provided for you as well as an initial supply of toiletries such as toilet roll, shampoos and shower gels. Very similar to how you would expect a stay at a good hotel. Also included is full access to everything the resort has to offer. Disney tickets are not included however we do offer the lowest prices on all tickets to our Top Villas guests.

How to book a stay

If you are ready to book a stay simply find the home you love, enter your dates and book instantly online today. If you have questions or would prefer one of our Orlando experts book the home in for you, simply contact us via chat, email or call us now on 866-341-8086

Reviews of the vacation homes at Windsor Hills

You can read reviews of our happy customers’ stays at Windsor Hills Resort on this page.

Other popular resorts in Orlando

Windsor Hills Resort is one of many great resorts in Orlando. You may also like to check out other popular resorts nearby, including: