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 May

See average prices and weather for all months

Price trends for hotels in Kissimmee

Pricing is based on two traveler single night rates
Jun
$137
Average price during June is $137
Jul
$148
Average price during July is $148
Aug
$139
Average price during August is $139
Sep
$147
Average price during September is $147
Oct
$165
Average price during October is $165
Nov
$156
Average price during November is $156
Dec
$208
Average price during December is $208
Jan
$141
Average price during January is $141
Feb
$147
Average price during February is $147
Mar
$151
Average price during March is $151
Apr
$138
Average price during April is $138
May
$133
Average price during May is $133
Currently viewing crowd sizes and weather for June.

June

trending_flatModerate crowds
High 88°F / low 74°F. Sunny most days.
88°
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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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90°
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July, High crowds, average high temperature 90 degrees Fahrenheit, average low temperature 76 degrees Fahrenheit. Sunny most days.
76°
90°
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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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87°
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September, Low crowds, average high temperature 87 degrees Fahrenheit, average low temperature 75 degrees Fahrenheit. Sunny most days.
75°
83°
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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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76°
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November, Low crowds, average high temperature 76 degrees Fahrenheit, average low temperature 62 degrees Fahrenheit. Sunny most days.
62°
73°
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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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69°
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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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74°
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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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78°
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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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82°
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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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86°
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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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Monthly weather averages (˚F)

Top landmarks in Kissimmee

Find out more about Windsor Hills

Find out more about Windsor Hills

Discover the Enchantment of Windsor Hills: Where Adventure Meets Serenity

Windsor Hills in Four Corners, Florida, is a vibrant vacation haven, perfectly situated for Disney World enthusiasts and theme park adventurers. This upscale residential community features luxurious villas, stunning pools, and a range of amenities tailored for families. Its fantastic location offers quick access to iconic attractions, including Disney Springs, while providing a serene retreat after a day of excitement. With beautiful landscapes and family-friendly facilities, Windsor Hills is the ideal base for creating unforgettable memories in the heart of Florida's entertainment paradise. Experience the magic of Disney and the charm of a welcoming resort all in one place! For great hotel rates in Windsor Hills, be sure to check out Hotels.com's Last-Minute DealsOpens in a new window on travel.

Discover great hotels in Windsor Hills

Windsor Hills is a vibrant resort community offering spacious condos and vacation rentals with fabulous amenities. Guests can enjoy world-class resort features such as pools, fitness centers, and recreational facilities, making it an ideal destination for a relaxing getaway in sunny Florida. Here are some of the best hotels in Windsor Hills that our travelers love:

  1. Encore Resort and Water Park At Reunion by RentylOpens in a new window: This luxurious 5.0-star resort is perfect for adventure seekers and beach lovers, providing direct access to pristine sandy shores. Guests can indulge in exceptional amenities including a meeting room, conference center, and a variety of onsite adventure sports such as swimming and ziplining. The property’s spacious accommodations create a comfortable and relaxing atmosphere, ensuring a memorable stay. Frequent travelers appreciate the smooth check-in process and the stunning upgrades that enhance their experience, making it an ideal choice for those seeking a high-end retreat.
  2. Westgate Town Center ResortOpens in a new window: This inviting 4.0-star resort is designed for families and pet owners alike, featuring a delightful array of amenities such as a children’s playground, pool, and arcade game room. Guests enjoy a vibrant atmosphere with various activities tailored for all ages. The location is highly convenient, with easy access to local attractions and a nearby Walmart. The friendly staff and well-maintained facilities contribute to an engaging environment, making it a favored destination for travelers seeking a fun and accommodating stay.
  3. Westgate Vacation Villas ResortOpens in a new window: This charming 4.0-star resort is a fantastic option for families, offering a wealth of activities and a water park for endless enjoyment. The beautifully renovated rooms showcase modern design, and the exceptional customer service enhances the overall experience. Amenities such as a children’s club and arcade game room ensure a lively atmosphere, making it an excellent choice for those looking to make lasting memories during their stay. The close proximity to local attractions adds to its appeal, providing guests with a seamless travel experience.

Top locations to stay in Windsor Hills

Staying in Windsor Hills, Four Corners, Florida, United States of America, puts you near Walt Disney World® Resort, Magic Kingdom® Park, and Disney's Animal Kingdom® Theme Park. Each offers unique experiences: Walt Disney World® Resort features diverse attractions; Magic Kingdom® Park captivates with its iconic castle and enchanting rides; and Disney's Animal Kingdom® Theme Park combines wildlife and adventure. For first-time visitors, staying near Magic Kingdom® Park is best, as it embodies the classic Disney experience.

  1. Near Walt Disney World® ResortOpens in a new window: Staying near Walt Disney World® Resort places you right in the heart of the magic. With a range of attractions including the iconic Magic Kingdom® Park and various shopping options like Disney Springs™, you’ll have endless opportunities for fun and excitement. Plus, cultural attractions like Wonderworks add to the vibrant atmosphere, making it a fantastic base for your adventures.
  2. Near Magic Kingdom® ParkOpens in a new window: When you choose to stay near Magic Kingdom® Park, you’re just steps away from enchanting experiences and captivating entertainment. This area boasts unique cultural spots like Sleuth's Mystery Dinner Show and a variety of shopping destinations such as Orlando International Premium Outlets. The majestic castle views and lively ambiance create an unforgettable backdrop for your stay.
  3. Near Disney's Animal Kingdom® Theme ParkOpens in a new window: Staying near Disney's Animal Kingdom® Theme Park immerses you in a world of wildlife and adventure. This vibrant area offers thrilling experiences at Aquatica and Disney's Typhoon Lagoon Water Park, along with shopping at the nearby Orlando International Premium Outlets. The blend of nature and excitement here makes it a great choice for those looking to explore beyond the typical theme park experience.

Things to do in Windsor Hills

Windsor Hills is a vibrant destination that perfectly blends thrilling water parks, lush recreational areas, and stunning natural landscapes. Enjoy exhilarating water slides, relax on serene beaches, or hit the golf course for a round with friends. With a range of shopping options and art experiences, this locale promises an unforgettable getaway.

  • Walt Disney World® ResortOpens in a new window – Dive into the magic at Walt Disney World® Resort, where you can explore a vast array of theme parks, film studios, and sports facilities. Enjoy thrilling rides, meet beloved characters, and experience a world of imagination and excitement.
  • Disney's Animal Kingdom® Theme ParkOpens in a new window – Venture into the wild at Disney's Animal Kingdom® Theme Park, where you can observe exotic animals in their natural habitats. Take part in exhilarating attractions and immerse yourself in the rich storytelling that brings the animal kingdom to life.
  • Universal Studios FloridaOpens in a new window – Unleash your inner movie buff at Universal Studios Florida. Experience heart-pounding rides and attractions based on your favorite films, and get a behind-the-scenes look at the magic of filmmaking and entertainment.
  • Magic Kingdom® ParkOpens in a new window – Step into a fairy tale at Magic Kingdom® Park, where iconic rides and enchanting parades await. From classic attractions to whimsical experiences, this park is a treasure trove of fun for visitors of all ages.
  • Epcot®Opens in a new window – Travel around the globe without leaving Florida at Epcot®. Discover innovative attractions, savor diverse cuisines, and explore cultural exhibits that celebrate the best of what our world has to offer.

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

  1. Book for the cheapest times: The most budget-friendly time to visit Windsor Hills is during August, September, and November, when hotel prices tend to be lower. For a great value for money experience, it's recommended to stay for at least 2 to 3 days to fully appreciate the area's historical landmarks and cultural attractions. You could explore notable sites such as the nearby theme parks, film studios, and sports facilities, making the most of your trip without breaking the bank.
  2. Look for last-minute deals on Hotels.com: To discover last-minute deals to Windsor Hills, begin by exploring the DealsOpens in a new window or Last-Minute DealsOpens in a new window sections on Hotels.com, where you may find discounted rates on accommodations close to your travel date. Consider enabling email alerts or push notifications for updates on flash sales and special promotions, ensuring you stay informed about potential savings. Additionally, the Smart ShoppingOpens in a new window tool in the app allows you to compare hotel prices and amenities, helping you make informed choices. This way, if rooms become available or prices drop, you could be among the first to seize a great deal for your getaway.
  3. Be flexible with dates: Prices can fluctuate depending on factors like the hotel's location, star rating, and the time of year. Being flexible with your travel dates may help you save on your stay at a Windsor Hills hotel. If you're interested in a distinctive experience, boutique hotels often provide a more personalized touch and can sometimes offer 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 find a more affordable option.
  4. Consider your location: Staying near major attractions or downtown areas can be convenient, but it often comes with a higher price tag. For more budget-friendly options, you might look at hotels in less central neighborhoods, where you can find a better balance between cost and accessibility to the sites you want to visit. Independent hotels located a bit further out usually tend to be more affordable and can offer a more authentic experience.
  5. Join One Key™: Become a One Key MemberOpens in a new window for free and book your next stay in Windsor Hills. Save on over 100,000 hotels worldwide with exclusive member prices. As a member, you can quickly progress through the tiers and enjoy perks, like free room upgrades when available and food and beverage discounts at select VIP Access properties.

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 typically the wettest month. If you’re looking to soak up the lively atmosphere in Windsor Hills, January, March, and April are the peak months to visit, bustling with fellow travelers. During this peak period, the weather is mostly sunny, accompanied by light rainfall. However, if you prefer a more relaxed experience, October to December are perfect for a quieter getaway, 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 Disney's Hollywood Studios®. Epcot® and Disney Springs™ 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)
  • Corpus Christi Catholic Church (3 mi/4.9 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)

Things to Do near Windsor Hills:

  • Disney's Animal Kingdom® Theme Park (2.7 mi/4.3 km away)
  • Disney's Hollywood Studios® (3.3 mi/5.4 km away)
  • Epcot® (4.6 mi/7.3 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?