Hotels in Windsor Hills

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Where to stay in Windsor Hills?

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 June

See average prices and weather for all months

Price trends for hotels in Kissimmee

Pricing is based on two traveller single night rates
May
CA $142
Average price during May is CA $142
Jun
CA $137
Average price during June is CA $137
Jul
CA $147
Average price during July is CA $147
Aug
CA $140
Average price during August is CA $140
Sep
CA $140
Average price during September is CA $140
Oct
CA $151
Average price during October is CA $151
Nov
CA $152
Average price during November is CA $152
Dec
CA $265
Average price during December is CA $265
Jan
CA $181
Average price during January is CA $181
Feb
CA $168
Average price during February is CA $168
Mar
CA $174
Average price during March is CA $174
Apr
CA $153
Average price during April is CA $153
Currently viewing crowd sizes and weather for May.

May

trending_downLow crowds
High 30°C / low 21°C. Sunny most days.
30°
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May, Low crowds, average high temperature 30 degrees Celsius, average low temperature 21 degrees Celsius. Sunny most days.
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31°
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June, Moderate crowds, average high temperature 31 degrees Celsius, average low temperature 24 degrees Celsius. Sunny most days.
24°
32°
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July, High crowds, average high temperature 32 degrees Celsius, average low temperature 25 degrees Celsius. Sunny most days.
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32°
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August, Low crowds, average high temperature 32 degrees Celsius, average low temperature 25 degrees Celsius. Partly sunny.
25°
31°
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September, Low crowds, average high temperature 31 degrees Celsius, average low temperature 24 degrees Celsius. Sunny most days.
24°
28°
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October, Moderate crowds, average high temperature 28 degrees Celsius, average low temperature 21 degrees Celsius. Sunny most days.
21°
25°
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November, Low crowds, average high temperature 25 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
17°
23°
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December, High crowds, average high temperature 23 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
21°
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January, Moderate crowds, average high temperature 21 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
12°
23°
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February, High crowds, average high temperature 23 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
25°
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March, High crowds, average high temperature 25 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
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28°
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April, Moderate crowds, average high temperature 28 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
Monthly weather averages (˚C)

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Find out more about Windsor Hills

Find out more about Windsor Hills

Unveiling Windsor Hills: Where Adventure Meets Enchantment in Every Corner

Nestled in the heart of Four Corners, Windsor Hills is a stunning resort destination that offers a perfect blend of relaxation and adventure. Known for its beautiful properties, this idyllic community is just a stone's throw from exhilarating theme parks and water parks, making it a favourite for families. Enjoy sun-soaked days by the pool or on the lush greens, and take advantage of nearby attractions like world-class golf courses and vibrant shopping. With its inviting atmosphere and proximity to Orlando's top attractions, Windsor Hills is the ultimate getaway for those seeking both excitement and tranquility in sunny Florida. For great hotel rates in Windsor Hills, be sure to check out Hotels.com's Last-Minute DealsOpens in a new window on travel.

Top locations to stay in Windsor Hills

Windsor Hills, Four Corners, Florida, is an ideal base for exploring magical attractions like Walt Disney World® Resort, Disney's Animal Kingdom® Theme Park, and Universal Studios Florida. Each offers unique experiences, but for first-time visitors, Walt Disney World® is the best choice, providing a quintessential Disney experience. Accommodations in these areas typically include well-appointed hotels with family-friendly amenities, while Windsor Hills vacation rentals offer spacious homes with resort-like amenities, including pools and recreational facilities for a comfortable stay. Here are some of the most popular hotels with our guests in Windsor Hills:

  1. Near Walt Disney World® ResortOpens in a new window: This area is perfect for families and entertainment enthusiasts, offering easy access to the magical experiences of Walt Disney World® Resort. The atmosphere is vibrant and fun, making it an ideal choice for family vacations. Hotels in this location include Four Seasons Resort Orlando at WALT DISNEY WORLD® ResortOpens in a new window, a 5-star resort offering excellent business amenities and family-friendly services such as a playground and arcade. Another option is Home2 Suites by Hilton Orlando at Flamingo CrossingsOpens in a new window, a 3-star hotel that accommodates pets and features a business center. Additionally, SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western EntranceOpens in a new window, also a 3-star property, provides essential business facilities for travellers.
  2. Near Disney's Animal Kingdom® Theme ParkOpens in a new window: This area is a family-friendly haven with a focus on nature and entertainment. Visitors can enjoy the thrill of the Animal Kingdom while staying close to other attractions. Orbit One ResortOpens in a new window is a 2.5-star hotel with fitness facilities, ideal for active guests. Orbit One Vacation VillasOpens in a new window, a 3-star hotel, features a shared playground and mini-golf, catering to families. Lastly, Quality Inn & Suites By the ParksOpens in a new window offers a blend of natural accommodation and business amenities, perfect for those looking to combine work and leisure.
  3. Near Universal Studios FloridaOpens in a new window: Known for its thrilling attractions and entertainment options, this location is a hit with families and those seeking adventure. Modern Twist. Perfect Location. Heated PoolOpens in a new window is a 2.5-star hotel that welcomes pets and provides family-friendly services like free cribs. For a more upscale experience, Universal's Hard Rock HotelOpens in a new window and Universal’s Loews Portofino Bay HotelOpens in a new window are both 4-star hotels offering a range of amenities including business centers and arcade rooms, making them suitable for both leisure and business travellers.

Things to do in Windsor Hills for first times

Windsor Hills is an ideal three-day getaway, offering a delightful mix of stunning beaches, lush parks, and scenic mountains. Visitors can enjoy thrilling theme parks, relaxing resorts, and vibrant shopping areas, alongside activities like boating, hiking, and golfing, making it a perfect destination for adventure and relaxation. Here's a quick itinerary to make the most of your trip to Windsor Hills:

  • Day 1: Begin your adventure at the iconic Walt Disney World® Resort, where you can immerse yourself in the magic of the theme parks and enjoy thrilling rides and enchanting attractions. After soaking in the Disney experience, take a leisurely trip to Buena Vista Place Dog Park, perfect for letting your furry friend stretch their legs and socialize with other dogs. Conclude your day at Waggin' Tails Dog Park, where both you and your pup can unwind in a relaxing environment, enjoying the beautiful Florida weather and the company of other dog lovers.
  • Day 2: Start your morning at Disney's Animal Kingdom® Theme Park, where you can embark on a wild journey through lush landscapes and encounter exotic wildlife. After a day of exploration, make your way to the serene Mary Queen of the Universe Shrine, a peaceful spot perfect for reflection and appreciation of art and architecture. Finish your day at the local Doggy Park, allowing your pet to play freely and enjoy some off-leash fun while you relax and chat with fellow pet owners.
  • Day 3: Kick off your day at the Orange County Convention Center, where you can explore various events and exhibitions happening during your visit. Following the excitement, head to Lake Bryan for a scenic stroll or a leisurely picnic by the water, taking in the natural beauty of the area. Wrap up your day at Universal CityWalk, where you can indulge in an array of dining options, shop for souvenirs, and enjoy vibrant nightlife, making it a perfect end to your trip.

4 tips to find a great Windsor Hills hotel deal

  1. Book for the cheapest times: The most affordable time to visit Windsor Hills is during August, September, and November, when hotel rates are notably lower. Domestic travellers should aim to book their flights at least 2 months in advance for the best prices, while international travellers are encouraged to secure their tickets at least 3 months ahead of time for budget-friendly options. To truly appreciate the region's highlights, a stay of at least 2-3 days is recommended. Key attractions in Windsor Hills include a popular theme park and a film studio, both offering great value for money for visitors on a budget.
  2. Look for last-minute deals on Hotels.com: If you're looking for great last-minute deals to Windsor Hills, consider checking out Hotels.com. By visiting the DealsOpens in a new window or Last-Minute DealsOpens in a new window section, you could find discounted rates on accommodations as your travel date approaches. To enhance your chances of landing a bargain, enable email alerts or push notifications from Hotels.com to keep you informed about flash sales and special promotions, helping you seize opportunities to save.
  3. Be flexible with dates: Prices can fluctuate due to factors like the hotel's location, star rating, and the time of year. As a result, being flexible with your travel dates may help you save on hotel expenses in Windsor Hills.
  4. Consider your location: When booking on Hotels.com for your holiday, take your location into account. Staying near major attractions or city centres may offer convenience, but it usually tends to come at a higher price. For more affordable options, consider hotels in less central areas or neighbourhoods, striking a balance between cost and the accessibility of the places you wish to explore.

Best time to go to Windsor Hills

Windsor Hills experiences its lowest average temperature in January, at 60.6°F (15.9°C), while August is the hottest month, with an average temperature of 82.6°F (28.1°C). August is usually the wettest month. January, March, and April are the peak travel months in Windsor Hills, attracting a higher number of tourists. During this peak period, the weather is mostly sunny, with light rainfall. On the other hand, October to December tend to be quieter times to visit, 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.

Where are the Best Places to Stay in Windsor Hills?

We have 1797 accommodations in the neighborhood. Some of the top places to stay in Windsor Hills:

Our DisneyDreamVilla - Salt water pool! Only minutes to DisneyWorld!!!

Family-friendly villa with private pool, kitchen
  • Free in-room WiFi • Water park • Spa tub • Outdoor pool • Attentive staff

🏝New Water Park!!! Huge Pool, 5 Minutes to Disney World!🏝

City-center condo with kitchen, balcony
  • Free in-room WiFi • Water park • Spa tub • Fitness center • Attentive staff

Free Water Park! Private Pool & Game Room (7739)

Vacation home with private pool, kitchen
  • Spa tub • Fitness center

Resort with free waterpark, 1 1/2 miles from Disney!

Family-friendly condo with kitchen, balcony
  • Spa tub • Fitness center • Tennis courts • Attentive staff

6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ

City-center vacation home with private pool, kitchen
  • Water park • Spa tub • Fitness center • Beach sun loungers • Central location

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?

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*Book by 5/26/2025 11:59 pm in hotel property local time. Stay between 4/17/2025-9/30/2025. Member Prices are available to Hotels.com™ app users and Hotels.com™ Rewards members. Limited availability, blackout periods may apply.

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