Windsor Hills, FL

Orlando

An aerial view of a residential area with numerous houses, roads, and several lakes.
A tree with hanging moss and green leaves against a clear blue sky.
A city skyline reflected in a calm lake with modern buildings and trees along the shore.
A palm tree with a brown trunk and red foliage, surrounded by green leaves and red flowers.
Orlando skyline with fireworks, theme park rides, and a castle.

Spend time in Windsor Hills to enjoy theme parks, water activities, shopping, and nearby neighborhoods filled with family-friendly options.

Windsor Hills is an ideal destination for family and entertainment travelers. Nearby, you can explore several major theme parks, including Walt Disney World® Resort, Epcot®, and Disney's Animal Kingdom® Theme Park. For those seeking water activities, Island H2O Live! provides a fun waterpark experience. Sports enthusiasts can visit the ESPN Wide World of Sports Complex, while golfers can enjoy a round at Mystic Dunes Golf Club. Additionally, you can find shopping options at Flamingo Crossings Town Center and Old Town, catering to various interests.

You can also explore Windsor Hills's nearby neighborhoods, each offering unique experiences. Celebration is known for its family-friendly attractions and features Celebration Golf Club, Corpus Christi Catholic Church, and Celebration Dog Park. Four Corners is another area that provides outdoor recreational opportunities, including Orange Lake Golf and Northeast Regional Park. Likewise, Lake Buena Vista is home to popular destinations such as Magic Kingdom® Park and Disney Springs™, making these nearby areas great for family entertainment.

The best time to visit Windsor Hills typically falls between May and August when the weather is warm and mostly dry, with temperatures ranging from 77 to 83°F. However, July to September sees increased rainfall. While demand for accommodations and experiences remains steady throughout the year, it tends to be busier in January and March to April, and quieter from October to December, allowing for a more relaxed visit if you choose to travel during those months.


Things to do


Windsor Hills Hotel Deals

Kissimmee Resort Villa, 4 Bed / 4 Bath En-Suite, Heated South Pool & AC Arcade

Kissimmee Resort Villa, 4 Bed / 4 Bath En-Suite, Heated South Pool & AC Arcade

Kissimmee FL
Book a stay at this family-friendly villa in Kissimmee. Enjoy free WiFi, private pools, and a fitness center. Our guests praise the pool and the property condition ...
9.8/10 Exceptional! (177 reviews)
"Not our first time staying in the community, but first time at this house. Loved it! Cozy, great layout, spacious. All of the amenities that you could ever need. One slight drawback was that my husband and I found the master suite bed to be uncomfortable, we ended up doing a next day Amazon purchase ..."

Reviewed on Nov 7, 2026

Kissimmee Resort Villa, 4 Bed / 4 Bath En-Suite, Heated South Pool & AC Arcade
Minutes Away from Theme Parks! 3-Bed Townhome, 6 minutes to Disney World!

Minutes Away from Theme Parks! 3-Bed Townhome, 6 minutes to Disney World!

Kissimmee FL
Book a stay at this family-friendly vacation home in Kissimmee. Enjoy free WiFi, private pools, and a fitness center. Our guests praise the helpful staff in ...
10/10 Exceptional! (220 reviews)
"My wife and I had a very enjoyable stay. We were very impressed with the level of cleanliness!"

Reviewed on Oct 30, 2026

Minutes Away from Theme Parks! 3-Bed Townhome, 6 minutes to Disney World!
Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community

Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community

Kissimmee FL
Book a stay at this family-friendly vacation home in Kissimmee. Enjoy free WiFi, private pools, and a garden. Popular attractions Disney's Animal Kingdom® Theme ...
9.6/10 Exceptional! (92 reviews)
"Very nice property in a gated community. Instructions for check-in were accurate and easy to follow. Host was responsive to messages and property manager was easy to get ahold of with any concerns. Good location to all the premiere attractions and dining options."

Reviewed on Oct 24, 2026

Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community
Newly Totally Renovated-Video Game Room-Private Pool

Newly Totally Renovated-Video Game Room-Private Pool

Kissimmee FL
Stay at this vacation home in Kissimmee. Enjoy private pools, a fitness center, and laundry facilities. Popular attractions ESPN Wide World of Sports Complex ...
Newly Totally Renovated-Video Game Room-Private Pool
Hidden Gem Resort Community Close to DISNEY!; 3BR/2BA w/ Water Park.

Hidden Gem Resort Community Close to DISNEY!; 3BR/2BA w/ Water Park.

Kissimmee FL
Book a stay at this family-friendly condo in Kissimmee. Enjoy free WiFi, a fitness center, and a garden. Popular attractions ESPN Wide World of Sports Complex ...
Hidden Gem Resort Community Close to DISNEY!; 3BR/2BA w/ Water Park.
Vacation in the Sun! Spacious 3 Bedroom, 6 minutes from Disney World!

Vacation in the Sun! Spacious 3 Bedroom, 6 minutes from Disney World!

Kissimmee FL
Book a stay at this family-friendly vacation home in Kissimmee. Enjoy free WiFi, private pools, and a fitness center. Our guests praise the helpful staff in ...
10/10 Exceptional! (130 reviews)
"The trip and home itself was perfect. Only problem we had was starting at about 11pm every night we were there it was constant loud banging and thumping like someone waiting til late at night to do work inside of their home and we really had a hard time sleeping. I came up with that conclusion because ..."

Reviewed on Nov 3, 2026

Vacation in the Sun! Spacious 3 Bedroom, 6 minutes from Disney World!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Where to stay in Windsor Hills

Find the best Windsor Hills areas and neighborhoods for the activities you enjoy most. Learn more about Windsor Hills
Learn more about Windsor Hills

Bay Lake

A noteworthy feature of Bay Lake is its exciting theme parks. While you're in town, be sure to stop and check out Epcot® and Walt Disney World® Resort.

International Drive District

Visitors to International Drive District rave about its breathtaking beach views, exciting theme parks, and popular shops. You might also want to make some time to see Orange County Convention Center or Orange County Convention Center North while you're exploring the neighborhood.

Florida Center

While visiting Florida Center, you might make a stop by sights like Universal Orlando Resort and Universal Studios Florida.

Champions Gate

Abundant dining options and pristine golf courses are well-reviewed features of Champions Gate. Make a stop by top sights like ChampionsGate Golf Club while you're exploring the area.

Reunion

The waterparks and pristine golf courses are top of the list for many visitors to Reunion. A stop by Reunion Resort Golf Course or Jack Nicklaus Course might round out your trip.



Windsor Hills, FL

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