Hotels in Windsor Hills

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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.
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Our prices for Kissimmee are cheapest in May

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Pricing is based on two traveler single night rates
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September
trending_downLow crowds
High 87°F / low 75°F. Sunny most days.
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September, Low crowds, average high temperature 87 degrees Fahrenheit, average low temperature 75 degrees Fahrenheit. Sunny most days.
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October, Moderate crowds, average high temperature 83 degrees Fahrenheit, average low temperature 69 degrees Fahrenheit. Sunny most days.
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November, Low crowds, average high temperature 76 degrees Fahrenheit, average low temperature 62 degrees Fahrenheit. Sunny most days.
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December, High crowds, average high temperature 73 degrees Fahrenheit, average low temperature 57 degrees Fahrenheit. Sunny most days.
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January, Moderate crowds, average high temperature 69 degrees Fahrenheit, average low temperature 53 degrees Fahrenheit. Sunny most days.
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February, High crowds, average high temperature 74 degrees Fahrenheit, average low temperature 57 degrees Fahrenheit. Sunny most days.
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March, High crowds, average high temperature 78 degrees Fahrenheit, average low temperature 59 degrees Fahrenheit. Sunny most days.
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April, Moderate crowds, average high temperature 82 degrees Fahrenheit, average low temperature 65 degrees Fahrenheit. Sunny most days.
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May, Low crowds, average high temperature 86 degrees Fahrenheit, average low temperature 69 degrees Fahrenheit. Sunny most days.
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June, Moderate crowds, average high temperature 88 degrees Fahrenheit, average low temperature 74 degrees Fahrenheit. Sunny most days.
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July, High crowds, average high temperature 90 degrees Fahrenheit, average low temperature 76 degrees Fahrenheit. Sunny most days.
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August, Low crowds, average high temperature 90 degrees Fahrenheit, average low temperature 77 degrees Fahrenheit. Partly sunny.
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Monthly weather averages (˚F)

Top landmarks in Kissimmee

Check out reviews of Windsor Hills hotels guests love

Frequently asked questions

Is Windsor Hills expensive to stay in?
You can find great hotels from $68 in Windsor Hills to suit a range of budgets. To find the best low-cost hotel on Hotels.com that meets your needs, apply your search filters and then sort hotels by "Price: low to high".
How can I find discounted rates and deals for Windsor Hills hotels?
Unlocking discounted rates at hotels in Windsor Hills couldn't be simpler. Members save up to 20% on select hotels when signed in. Silver, Gold, and Platinum members can earn additional rewards on VIP Access bookings.
Can I receive a refund if I cancel my Windsor Hills hotel booking?
The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel your booking. Some Windsor Hills hotels require you to cancel more than 24 hours before check-in, so look at your booking beforehand. For extra peace of mind before you book, filter hotels by "Property cancellation options" and select "Fully refundable property".
What are some of the best family hotels in Windsor Hills?
If you're vacationing with your family, Windsor Hills Resort Homes, Townhomes & Condos is one of the best family hotels in Windsor Hills. Windsor Hills Resort Homes, Townhomes & Condos has a great average guest score of 6.4 out of 10 and amenities like an indoor pool, an arcade/game room and in-room cribs. To explore more family hotels in Windsor Hills, use the "Family friendly" filter in your search on Hotels.com.
What are some of the best Windsor Hills hotels with a pool?
Book a Windsor Hills hotel with a pool for some added relaxation or exercise on your trip. Windsor Hills Resort Homes by Atlas VH is a top-rated hotel with an outdoor pool and a children's pool, and an average guest score of 9 out of 10. This hotel also features a bar/lounge and a gym. Windsor Hills Resort Homes, Townhomes & Condos is another great resort that features an indoor pool, along with a hot tub and a restaurant. For more Windsor Hills hotels with a pool, use the "Amenities" filter in your search and select "Pool" on Hotels.com.
What are some of the top Windsor Hills hotels with free parking?
If you're traveling by car, make your life easier by booking a Windsor Hills hotel with free parking. Our travelers like:
Is it worth staying in Windsor Hills?
You're spoilt for choice with 1,783 hotels in the area so it's easy to find your perfect somewhere. Basing yourself in Windsor Hills makes it easy to explore Kissimmee, including the neighborhoods of Bay Lake and Reunion.
What are some great hotels in Windsor Hills with balconies?
There are some top hotels in Windsor Hills that offer rooms with a balcony. Check out Windsor Hills Resort Homes, Townhomes & Condos which has a high guest score of 6.4 out of 10, and balconies in some rooms.
Are all taxes and fees included in the Windsor Hills hotel prices shown on Hotels.com?
Hotels.com provides upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.

Find out more about Windsor Hills

Find out more about Windsor Hills

Discover the Magic of Windsor Hills: Where Dreams and Nature Converge

Discover Windsor Hills, a premier resort community in Four Corners, Florida, perfect for family vacations just minutes from Orlando's thrilling theme parks. This enchanting destination features luxurious vacation homes, a stunning water park, and an array of recreational facilities, making it an ideal retreat for relaxation and adventure alike. Enjoy sunny days lounging by the pool, engaging in sports, or exploring nearby attractions like Walt Disney World. With its welcoming atmosphere and vibrant amenities, Windsor Hills promises unforgettable experiences for families and travelers seeking both fun and comfort in the heart of Florida.

Discover great hotels in Windsor Hills

Windsor Hills offers a variety of vacation villas and resort accommodations perfect for families and groups. Enjoy fantastic amenities like pools, fitness centers, and game rooms. With convenient access to nearby attractions, Windsor Hills rentals provide a comfortable and fun base for your Florida adventure. Here are some of the best hotels in Windsor Hills that our travelers love:

  1. Hilton Vacation Club Mystic Dunes OrlandoOpens in a new window: This 3.5-star hotel is ideal for leisure travelers seeking a distinctive family vacation experience. It features a range of engaging amenities, including an arcade game room, mini-golf, and various games, ensuring a fun-filled stay. The property also boasts a well-equipped business center that supports a seamless travel experience. The standout features enhance the overall comfort and enjoyment, making it a popular choice among frequent travelers who appreciate vibrant atmospheres combined with family-friendly options.
  2. Westgate ResortsOpens in a new window: This property is a delightful choice for leisure travelers craving an active getaway. With a 24-hour fitness facility and diverse dining options, including a coffee shop and restaurant, it caters to those who value both physical wellness and culinary experiences. The inviting ambiance and recreational activities promote relaxation and rejuvenation, making it an attractive destination for travelers looking to unwind while enjoying their stay.
  3. Westgate ResortOpens in a new window: This hotel offers a luxurious retreat for travelers who prioritize wellness and relaxation. With a full-service spa and an outdoor pool, it provides the perfect setting for unwinding after a day of exploration. The property welcomes pets, aligning with the needs of pet-centric travelers who seek high-end accommodations. The unique blend of spa services and upscale amenities creates an inviting atmosphere, appealing to those seeking a serene escape in a stylish environment.

Top locations to stay in Windsor Hills

Staying in Windsor Hills, Four Corners, Florida, United States of America, places you near Walt Disney World® Resort, Disney's Animal Kingdom® Theme Park, and Magic Kingdom® Park. Walt Disney World® Resort offers diverse attractions and shopping; Disney's Animal Kingdom® immerses you in wildlife adventures, and Magic Kingdom® Park captivates with classic Disney magic. For first-time visitors, staying near Magic Kingdom® Park is highly recommended.

  1. Near Walt Disney World® ResortOpens in a new window: Staying near Walt Disney World® Resort puts you in the heart of magical experiences and excitement. Explore its iconic attractions, from thrilling rides to enchanting shows. Enjoy shopping at Disney Springs™, where you'll find a variety of shops and entertainment options. For relaxation, check out the wellness offerings like Mystic Dunes Golf Club, perfect for unwinding after a day at the parks.
  2. Near Disney's Animal Kingdom® Theme ParkOpens in a new window: When you stay near Disney's Animal Kingdom® Theme Park, you're just steps away from a unique blend of adventure and nature. Discover wildlife and immersive experiences that bring you closer to the animal kingdom. For shopping, visit nearby Orlando Vineland Premium Outlets, where you can find great deals. Additionally, enjoy cultural attractions like Medieval Times that showcase engaging performances.
  3. Near Magic Kingdom® ParkOpens in a new window: Choosing to stay near Magic Kingdom® Park means you're right next to the classic Disney experience. This iconic park offers a range of attractions that delight visitors of all ages. You can also explore exciting nearby adventures at Disney's Typhoon Lagoon Water Park or Aquatica. For a bit of leisure, enjoy the scenic surroundings at Waldorf Astoria Golf Club, providing a serene escape close to the fun.

Things to do near Windsor Hills

Windsor Hills is an ideal family getaway, blending stunning landscapes with endless fun. Enjoy vibrant resort pools, exciting theme parks, and thrilling water parks. Explore lush parks for hiking or unwind at scenic lakes. With shopping options and golf courses nearby, there's something for everyone to enjoy!

  • Walt Disney World® ResortOpens in a new window – Dive into the magic of this iconic theme park, where you can experience thrilling rides, meet beloved characters, and enjoy spectacular parades. From enchanting castles to immersive attractions, every corner of this resort sparks joy and wonder.
  • Universal Studios FloridaOpens in a new window – Step into the world of movies at Universal Studios Florida! Experience rides and shows inspired by your favorite films, and don’t miss the chance to explore interactive attractions that bring the silver screen to life. Perfect for families and film buffs alike!
  • Universal Orlando ResortOpens in a new window – Discover the ultimate entertainment destination at Universal Orlando Resort. This sprawling complex features exciting rides, themed dining, and unforgettable experiences that cater to all ages. Don’t forget to visit the Wizarding World of Harry Potter for a truly magical experience!
  • Magic Kingdom® ParkOpens in a new window – Journey into a realm of fantasy and adventure at Magic Kingdom® Park. With classic attractions like Space Mountain and Cinderella Castle, this park is filled with thrilling rides, delightful shows, and unique dining options that will create lasting memories for you and your family.

5 tips for savvy savings when booking a hotel in Windsor Hills

  1. Book for the cheapest times: The most affordable time to visit Windsor Hills is during August, September, and November, when hotel prices may drop. For a budget-friendly getaway, staying at least 4 to 5 days is recommended to fully experience the area's key landmarks and cultural sites. During your visit, you can explore attractions like the visitor center, historic sites, art galleries, and nature reserves, making it a great value for money trip where you can immerse yourself in the local history and culture.
  2. Look for last-minute deals on Hotels.com: To find last-minute deals for Windsor Hills, you may discover great offers by visiting the DealsOpens in a new window or Last-Minute DealsOpens in a new window sections on Hotels.com, where discounted rates on nearby hotels are often listed close to your travel date. You could also enable email alerts or push notifications from Hotels.com to stay informed about flash sales and special promotions. Additionally, the Smart ShoppingOpens in a new window tool available via the app allows you to compare hotel prices and amenities, so if rooms become available or prices drop, you're more likely to see these opportunities for savings and book your last-minute getaway.
  3. Be flexible with dates: Prices can fluctuate based on factors like the hotel's location, star rating, and the time of year, so being flexible with your travel dates could help you save on your stay at a Windsor Hills hotel. If you're interested in unique accommodations, boutique hotels may provide a more personalized experience and potentially better value. When you book through Hotels.com, we’ll inform you if the price for your chosen dates is above or below the average. If the price is on the higher end, we’ll suggest alternative dates that could help you score a better deal.
  4. Consider your location: Staying close to major attractions or city centers can be convenient, but it often comes with a higher price tag. If you're looking for more budget-friendly options, consider hotels in less central neighborhoods, where you can find a better balance between cost and accessibility to the sites you want to visit. You might also look into independent hotels a bit farther out, as they usually tend to be more affordable and can offer a more authentic experience.
  5. Become a Member: Join our membership program for free and start booking your next stay in Windsor Hills today! Enjoy exclusive member prices and save on over 100,000 hotels worldwide. As a valued member, you'll have the opportunity to quickly advance through our tier system, unlocking fantastic perks such as complimentary room upgrades (when available) and special food and beverage discounts at select VIP Access properties. Don't miss out on these exclusive benefits—sign up now and make your travel experience even more enjoyable!

Best time to go to Windsor Hills

Windsor Hills has a varied climate due to its size, so the best time to visit depends on the region and your preferences for weather and crowds. The peak travel months to visit Windsor Hills are January, March, and April, which see a higher number of tourists. During this peak period, the weather is mostly sunny, accompanied by light rainfall. In contrast, October to December are ideal if you're looking for a calmer vacation, marked by no to light rainfall and mostly sunny conditions.

What's Windsor Hills Like?

If you want to find the perfect part of the city to explore, why not consider Windsor Hills? Top places in the larger area to visit include Disney's Animal Kingdom® Theme Park and Epcot®. Disney Springs™ and Walt Disney World® Resort are a couple of popular sights nearby.

How to Get to Windsor Hills

Flying to:

  • Kissimmee, FL (ISM-Kissimmee Gateway), 10 mi (16 km) from Windsor Hills
  • Orlando Intl. Airport (MCO), 19.2 mi (30.8 km) from Windsor Hills

Things to See and Do in and around Windsor Hills

Things to See near Windsor Hills:

  • ESPN Wide World of Sports Complex (2.7 mi/4.4 km away)
  • Lake Davenport (3.8 mi/6.2 km away)
  • Northeast Regional Park (4.1 mi/6.6 km away)
  • Melt-Away Bay (2.5 mi/4 km away)
  • Champion Stadium (2.7 mi/4.4 km away)

Things to Do near Windsor Hills:

  • Disney's Animal Kingdom® Theme Park (2.7 mi/4.3 km away)
  • Epcot® (4.6 mi/7.3 km away)
  • Disney's Hollywood Studios® (3.3 mi/5.4 km away)
  • Old Town (5 mi/8 km away)
  • Mystic Dunes Golf Club (0.7 mi/1.1 km away)

When Is the Best Time to Visit Four Corners?

  • Hottest months: August, July, June, September (average 81°F)
  • Coldest months: January, February, December, March (average 64°F)
  • Rainiest months: August, July, September, June (average 9 inches of rainfall)

Windsor Hills Travel Information

Best Time to Visit
March, April and June
Average Stay
6 days
Closest Neighborhoods
Aldea Reserve, Pinewood Country Estates
Top Attractions
Orange Lake Golf, Jack Nicklaus Course

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