About Windsor Hills Resort

The Windsor Hills Resort is a 24-hour secure gated resort community located less than 2 miles from Walt Disney World making it the closest resort community to the major theme parks. Since it opened in 2006, Windsor Hills has firmly secured its position as the most popular private rental community in Orlando. Windsor Hills is the perfect retreat to escape the frenetic atmosphere of the parks. Easy to get to and only a 20-minutes drive from Disney by car or bus, it provides the optimal base for a full day at the parks then some well-earned rest in the comfort of your own home away from home. Windsor Hills offers peace and tranquility and a luxurious accommodation option as an alternative to staying on-site at Disney. Alternatively the resort acts as the ideal golf holiday location, located next door to the excellent Mystic Dunes Golf Club and within easy reach of a wide array of golf courses in the Kissimmee area (across all ability levels and budgets) so there are plenty of options and a week or two of full on golf, playing a different course every day, is easily achieved with Windsor Hills as your base.

Resort Amenities

Windsor Hills offers all the amenities you would expect in a five-star resort complex, including a double Olympic size resort swimming pool with a waterpark area (newly opened in late 2018); a children’s play area with miniature castle, slides, and swings; a golf putting green; tennis, volleyball, and basketball courts; and a first class clubhouse over-looking the main resort pool area.

The resort clubhouse complex features the pool and waterpark, state-of-the-art fitness center, games room with billiards, table tennis and video arcade, a grocery store/deli, high-definition surround sound movie theatre, BBQ gazebo and a secure 24-hour gated and guarded entrance. Your family could enjoy an entire vacation just playing and relaxing in the amazing Windsor Hills resort pool area and clubhouse.

Everything within the resort is free except for possibly certain sporting equipment rental. Check with the resort Welcome Center on the way to the pool for more details.

Windsor Hills resort clubhouse and pool area is open all year round. The clubhouse is open daily from 8am to 10pm and is a good first point of contact for any general queries you might have during your stay. The pool is open daily from 8am to 10pm. The water slide and kids pool area are open 10am daily all year round and closes at 8pm in high season (April – September) and at 6pm in low season (October to March).

Why Windsor Hills?

Windsor Hills has a mature owner rentals model with a very strong home owners association who make it their mission to ensure guests to the resort have as pleasant and enjoyable an experience as possible so renting in Windsor Hills guarantees you peace of mind and deals abound especially during less popular times of the year such as September. Since development began in 2005 the resort has steadily increased in popularity and is now the first choice for most returning Orlando holidaymakers who want to stay off-site at Disney. Unlike most other short term rental resorts Windsor Hills offers a broad range of properties across all 3 major accommodation types: condo, townhome, detached villa home. Most homes in Windsor Hills are solely for short term rentals and thus the resort retains a spirit and buzz more attune to a holiday complex than a residential community. The majority of properties are hands-on managed by owners who usually only contract out day to day management of the actual property such as cleaning and helping guests with any queries they have during their stay. The resort is relatively compact so long walks to the clubhouse and swimming pool are rare. Take some time to decide where to stay in Windsor Hills. There are tennis courts, clubhouse with main pool and kids play area; all of which you may want to be close to depending on your plans. In short, rent direct from owners in Windsor Hills Resort to stay in Orlando’s most popular and well located resort community.

Restaurants, Shops, Grocery Nearby

For most of your grocery needs, we recommend Publix, located 3 miles from Windsor Hills on the north side of 192 just before you get to Hwy 429. Across 192 from the Publix is a Super Target, which also has food and pretty much anything else you might need during your stay. The fresh food will be much better at Publix, but everything else will be less expensive at Super Target. Another – less busy – Publix is located down Old Lake Wilson Road about five miles south of Windsor Hills, just turn right after leaving the security gate and you’ll see it on the right. The Super Wal-Mart on Old Lake Wilson Road near Hwy 192 is cheaper than Target, more convenient than all of the above for the usual food items, usually good quality vegetables and fruits, but lower quality on the fresh meats.

One of our guests recommended the SHIPT app (see www.shipt.com) to us, which provides a local “shopper” to pick up your groceries and deliver them to you for a small fee. If you’re pressed for time, check them out on your Android or IOS devices.

For nearby restaurants, Kissimmee has a wide assortment. We recommend you avoid most of the garishly lit tourist-trap restaurants along the 192 “strip”.

The Bob Evans is great for breakfast, as is the Cracker Barrel and IHOP… all are on 192 near Old Lake Wilson Rd. For a special treat for the kids, we highly recommend the “character breakfasts” that are available at several of the Disney resort hotels… and then take the free bus from the hotel to any of the Disney parks and save the parking fees. We recommend you get reservations for the character breakfasts long before you arrive, because the best times often get filled early.

We recommend Flippers next to the Super Target on 192 for pizza. Also in that same complex of stores is Longhorn Steakhouse – very good for steak, chicken, ribs, and salads – and Olive Garden, which has good Italian food and an endless salad. The town of Celebration is a trendy area to walk around with lots of nice restaurants, check it out one evening! No one recommends Asian food in the area; your best bet appears to be to go up I-4 to Orlando. All the restaurants in the area will do eat-in or take-out.

We love Disney Springs for dinner, several options there that will appeal to you and the kids. And while you’re there, take the kids over to Ghirardelli’s for an amazing ice cream sundae.

During the winter months, you can get fresh stone crabs – a Florida favorite – at Johnny’s Hideaway. For decent kid-friendly Mexican food, go to Chevy’s.  Both are in the Crossroads shopping center area on State Road 536 (S. Apopka-Vineland Road) at the end of Buena Vista Drive (the road that runs along Disney Springs). Give yourself extra time to get there, traffic in that area is terrible most of the time.

If you’re near Universal Studios or just up for a 20-minute drive to get good deli food, check out TooJay’s Gourmet Deli on Sand Lake Road and Dr. Phillips Drive. A block west of there is the Dellagio shopping area, which has a number of very good upscale restaurants.

If you find other restaurants you feel are worthy additions, let us know!

Location Closest To Disney

Windsor Hills is only 2 miles from Walt Disney World! Swim in or relax next to the amazing resort pool, visit one of the many nearby theme parks, play golf at one of the many Orlando championship courses, right next door is Mystic Dunes! (rated the second best course in the Orlando area). Only a 5 minute drive (through 2 sets of traffic lights!) to Disney. Note – there are on-site resorts (part of the WDW complex) on Disney property that are farther from some of the parks than Windsor Hills. You can visit the parks in the morning, come back for a dip in the pool and be back in the parks for dinner and fireworks with ease. Other Orlando attractions like Sea World, Universal Studios and International Drive are less than 15 minutes away. For golfers, Mystic Dunes is right next door as well as the fantastic Disney courses and the championship courses at Reunion and Champions Gate are less than 10 minutes away. Amazing deals can be had on Golf Courses in Kissimmee and Windsor Hills is perfectly located to benefit you. Orlando International Airport is an easy 30 minute drive along the 417 from Windsor Hills. Orlando Sanford Airport is of similar distance.

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