An aerial view of a residential area with numerous houses, roads, and several lakes.

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Our top choices for Windsor Hills hotels

1. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4.0 star property
6.5 mi from Windsor Hills
9.2 out of 10, Wonderful, (7,258 reviews)
"great place to stay!"
United States
Julie
$111 nightly
The price is $125
Nov 29 - Nov 30
Total with taxes and fees
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

2. The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
4.0 star property
4.2 mi from Windsor Hills
8.2 out of 10, Very good, (10,922 reviews)
"Great place to stay!"
United States
Jessica
$219 nightly
The price is $246
Dec 7 - Dec 8
Total with taxes and fees
The Grove Resort & Water Park Orlando

3. Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
3.0 star property
1.1 mi from Windsor Hills
9.4 out of 10, Exceptional, (6,378 reviews)
"Good location and perfect for families!"
United States
Mayrah
$61 nightly
The price is $69
Nov 9 - Nov 10
Total with taxes and fees
Kompose Boutique Resort at Theme Parks

4. Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark
4.0 star property
1.6 mi from Windsor Hills
8.8 out of 10, Excellent, (3,785 reviews)
"Great stay"
United States
Samuel
$164 nightly
The price is $186
Nov 29 - Nov 30
Total with taxes and fees
Margaritaville Resort Orlando with H2O Waterpark

5. Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort
3.5 star property
12.6 mi from Windsor Hills
9.0 out of 10, Wonderful, (7,853 reviews)
"Great hotel"
United States
Xeulem
$171 nightly
The price is $192
Nov 8 - Nov 9
Total with taxes and fees
Universal's Cabana Bay Beach Resort

6. Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
4.0 star property
8.6 mi from Windsor Hills
9.2 out of 10, Wonderful, (4,248 reviews)
"Great place to stay with the family."
United States
Vanessa
$96 nightly
The price is $108
Nov 29 - Nov 30
Total with taxes and fees
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

7. Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando
4.0 star property
0.5 mi from Windsor Hills
9.0 out of 10, Wonderful, (4,820 reviews)
"Awsome place to stay friendly staff clean safe and close to everything"
United States
Charles
$124 nightly
The price is $141
Nov 15 - Nov 16
Total with taxes and fees
Hilton Vacation Club Mystic Dunes Orlando

8. Walt Disney World Dolphin

Walt Disney World Dolphin
4.0 star property
3.9 mi from Windsor Hills
9.0 out of 10, Wonderful, (4,759 reviews)
"Excellent stay"
United States
Alana
$220 nightly
The price is $248
Nov 29 - Nov 30
Total with taxes and fees
Walt Disney World Dolphin

9. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
3.0 star property
4.4 mi from Windsor Hills
9.4 out of 10, Exceptional, (5,724 reviews)
"Great location, breakfast, clean, and very nice and helpful staff!"
United States
Robert
$76 nightly
The price is $85
Nov 24 - Nov 25
Total with taxes and fees
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

10. Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
4.4 mi from Windsor Hills
9.4 out of 10, Exceptional, (6,261 reviews)
"Fantastic hotel, loved every minute of our stay!"
United States
Melissa
$98 nightly
The price is $110
Nov 29 - Nov 30
Total with taxes and fees
Home2 Suites by Hilton Orlando at Flamingo Crossings

11. Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
4.1 mi from Windsor Hills
8.6 out of 10, Excellent, (5,275 reviews)
"Great place to stay at a great place."
United States
Desiree
$104 nightly
The price is $118
Nov 29 - Nov 30
Total with taxes and fees
Vacation Village Orlando, Celebration

12. Embassy Suites By Hilton Orlando Sunset Walk

Embassy Suites By Hilton Orlando Sunset Walk
4.0 star property
1.6 mi from Windsor Hills
9.4 out of 10, Exceptional, (1,228 reviews)
"Great stay"
United States
Yosset
$130 nightly
The price is $148
Dec 6 - Dec 7
Total with taxes and fees
Embassy Suites By Hilton Orlando Sunset Walk

13. Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG
4.0 star property
Orange Lake, 2.8 mi from Windsor Hills
8.8 out of 10, Excellent, (3,415 reviews)
"Great location and facilities."
United States
Maria
$158 nightly
The price is $178
Nov 16 - Nov 17
Total with taxes and fees
Holiday Inn Club Vacations at Orange Lake Resort by IHG

14. Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area
4.0 star property
6.7 mi from Windsor Hills
9.8 out of 10, Exceptional, (6,224 reviews)
"Best place ever to stay!"
United States
Jace
$174 nightly
The price is $196
Nov 23 - Nov 24
Total with taxes and fees
Drury Plaza Hotel Orlando - Disney Springs Area

15. Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
4.0 star property
1.8 mi from Windsor Hills
9.0 out of 10, Wonderful, (2,357 reviews)
"Amazing stay, staff was so nice and the property was beautiful! Definitely will be visiting again!"
United States
Ashley
$417 nightly
The price is $474
Nov 11 - Nov 12
Total with taxes and fees
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

16. Evermore Orlando Resort

Evermore Orlando Resort
4.0 star property
7.1 mi from Windsor Hills
9.6 out of 10, Exceptional, (859 reviews)
"Perfect for a family stay"
United States
Annika
Evermore Orlando Resort

17. Wyndham Grand Orlando Resort Bonnet Creek

Wyndham Grand Orlando Resort Bonnet Creek
4.0 star property
4.5 mi from Windsor Hills
8.8 out of 10, Excellent, (3,176 reviews)
"Great experience, will definitely stay here in the future!"
United States
Oscar
$193 nightly
The price is $217
Nov 15 - Nov 16
Total with taxes and fees
Wyndham Grand Orlando Resort Bonnet Creek

18. Westgate Town Center Resort

Westgate Town Center Resort
4.0 star property
0.6 mi from Windsor Hills
8.2 out of 10, Very good, (2,067 reviews)
"Great hotel clean rooms friendly staff"
United States
Angelina
$120 nightly
The price is $137
Nov 8 - Nov 9
Total with taxes and fees
Westgate Town Center Resort

19. Westgate Vacation Villas Resort

Westgate Vacation Villas Resort
4.0 star property
0.6 mi from Windsor Hills
8.2 out of 10, Very good, (2,131 reviews)
"Great place to stay!)"
United States
Autumn
$114 nightly
The price is $130
Nov 11 - Nov 12
Total with taxes and fees
Westgate Vacation Villas Resort

20. Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG
3.5 star property
5.9 mi from Windsor Hills
7.8 out of 10, Good, (1,219 reviews)
"This was a great resort. Really enjoyed staying there."
United States
Nikisha
$139 nightly
The price is $156
Nov 8 - Nov 9
Total with taxes and fees
Holiday Inn Resort Orlando Suites - Waterpark by IHG
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

Home to all four Walt Disney World Resort theme parks and one water park, this city offers endless entertainment, including Disney's Fort Wilderness Resort & Campground and Magnolia and Palm Golf Courses.

International Drive District

Adventure activities, iconic attractions, shopping and world-class dining destinations make this famous street one of Orlando’s most popular tourist attractions.

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.

Top Windsor Hills Hotel Reviews

Find out more about Windsor Hills

Top reasons to visit Windsor Hills

  • Family-Friendly Atmosphere: Windsor Hills is designed for family vacations, offering a welcoming environment with plenty of activities for all ages.
  • Proximity to Theme Parks: Located near iconic attractions like Disney World, it serves as the perfect base for adventure seekers.
  • Recreational Activities: Enjoy a variety of outdoor fun, including water parks, golf courses, and serene lakes.
  • Diverse Accommodation Options: Choose from vacation rentals and resort villas that cater to families, couples, and even pets.
  • Vibrant Community: Experience a lively atmosphere with friendly locals and a range of shopping and dining options.

Find great hotels near Windsor Hills

Windsor Hills offers a fantastic selection of hotel accommodations, perfect for families, pet-friendly travelers, and couples seeking a romantic getaway. With options including Windsor Hills vacation rentals and resort villas, you'll find the ideal home base for your Orlando adventures. Enjoy the comfort of resort amenities while being just minutes away from world-class attractions. Whether you’re here for relaxation or excitement, Windsor Hills has the perfect lodging to meet your needs.

  • Hilton Vacation Club Aqua Sol Orlando West: This 3.5-star hotel, with a guest rating of 8.8, offers a delightful family vacation experience just 4 miles from Windsor Hills. The hotel provides a plethora of amenities tailored for children, including a fun-filled water park, an arcade game room, and a playground. Families can also enjoy a refreshing pool designed for kids, ensuring that younger guests stay entertained and engaged. The welcoming atmosphere and family-friendly services make it an ideal choice for those seeking a memorable getaway.
  • Hilton Vacation Club Mystic Dunes Orlando: A 3.5-star property rated 9.0 by guests, Hilton Vacation Club Mystic Dunes Orlando is located a mere 0.5 miles from Windsor Hills. This golf-themed resort is perfect for families and golf enthusiasts alike, featuring an on-site mini golf course and a variety of games. Children will love the ping pong table, as well as the dedicated pool area designed just for them. With its blend of family fun and golf experiences, this hotel is a fantastic choice for a vacation that caters to all ages.
  • Walt Disney World Dolphin: Rated 8.8 and classified as a 4-star hotel, Walt Disney World Dolphin is situated 4 miles from Windsor Hills. This beach-themed resort offers guests direct access to the beach while also catering to golf lovers with its on-site golf facilities. Families will appreciate the amenities for children, such as supervised childcare, a dedicated children's club, and a pool just for kids. The combination of beach relaxation and family-oriented activities makes this hotel a superb choice for a fun-filled vacation.

Where to stay near Windsor Hills

Windsor Hills, nestled in Four Corners, Florida, is the perfect family-friendly destination for a memorable vacation. Enjoy the vibrant atmosphere filled with friendly locals and recreational activities. Visit the Windsor Hills Resort for a variety of entertainment options, or relax at the nearby recreation center. Just a short drive away, you'll discover attractions like Disney World and other exciting excursions, making it an ideal base for exploring the magic of Central Florida.

  • Orlando: A vibrant metropolis, Orlando is famed for its family-friendly attractions and entertainment options. Located in close proximity to Windsor Hills, the city experiences a steady influx of visitors year-round, with peak travel times occurring in March, July, and December. Orlando offers a plethora of activities, including world-renowned theme parks, shopping areas, and an arts center that showcases local talent. Notable landmarks nearby include stunning theme parks, a famous film studio, and beautiful beaches, making it an ideal destination for both relaxation and excitement.
  • Four Corners: Positioned as a charming village, Four Corners is where Windsor Hills is nestled, offering a unique blend of family-oriented and outdoor experiences. This area sees its peak visitor numbers from February to March and in July, with a quieter atmosphere during August and the autumn months. Four Corners boasts a variety of amenities, including luxurious resorts and top-notch golf courses. Its proximity to major attractions like theme parks, a film studio, and sports facilities ensures that visitors have plenty of entertainment options to explore during their stay.
  • Lake Buena Vista: Just 6 miles from Windsor Hills, Lake Buena Vista is a dynamic city known for its family-oriented and business-friendly environment. The city also attracts travelers during peak seasons from January to March and experiences a slight decline in visitors from October to December. Visitors can enjoy upscale shopping areas and malls while being close to legendary theme parks and entertainment venues. With its blend of leisure and excitement, Lake Buena Vista is perfect for those looking to experience the best of Central Florida.

Things to do near Windsor Hills

Windsor Hills is a perfect destination for family-friendly vacations, offering a blend of entertainment and relaxation. Nearby, you can explore popular attractions like Busch Gardens Tampa, enjoy thrilling water parks, or tee off at local golf courses. With a variety of recreation options and shopping areas, there's something for everyone to enjoy, making it an ideal getaway experience for travelers seeking both fun and leisure.

Shopping

In Windsor Hills, visit the nearby Orlando Vineland Premium Outlets for fantastic deals on designer brands and souvenirs. For a local experience, check out the Kissimmee Lakefront Park Market, where you can find unique crafts and gifts from local artisans, just a short drive away.

Recreation

At Ridgewood Lakes Golf and Country Club, enjoy a round of golf amidst luxury vibes just 9 miles from Windsor Hills. Windermere Country Club offers a similar upscale experience 13 miles away, while Rio Pinar Country Club, located 25 miles from Windsor Hills, features scenic views and a serene atmosphere.

Adventure

Explore the thrilling water slides and lazy river at the Windsor Hills Water Park for a fun-filled day. For a different adventure, head to nearby Kissimmee Lakefront Park for kayaking and paddleboarding, enjoying the serene lake views and wildlife encounters.

Nightlife

In Windsor Hills, the nightlife offers a relaxing vibe with cozy bars and family-friendly entertainment. Nearby, you can explore lively spots like Old Town Kissimmee for rides and music, or venture to Disney Springs for dining and live performances, ensuring a memorable evening out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Windsor Hills

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Windsor Hills are August to September and November, where the prices are slightly lower. This is in comparison to March to April and December, where prices are slightly higher.
  • The best time to book a hotel: Book your hotel around Windsor Hills about 1 month out to secure some of the cheapest prices. If you're the spontaneous type, Expedia's last minute deals and discounts are indicated via the green label below the price.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Windsor Hills is Tuesday. The most expensive day to stay around Windsor Hills is Saturday.
  • Find cheap hotels on Expedia: Expedia's search tool enables you to set your budget, choose your desired location, and much more. You can organize your search results by price, starting with the most affordable hotels. Additionally, you can refine your options by hotel category—if you check the Eco-certified filter, you'll find a selection of sustainable and eco-friendly hotels ready for booking.
  • Consider bundling your trip: You can save money by combining your hotel stay at Windsor Hills with your flights and activities through an Expedia package deal.

Find the best attractions near Windsor Hills

Windsor Hills is perfect for family vacations and entertainment-themed getaways. Visitors can enjoy nearby attractions such as thrilling theme parks, serene lakes, and scenic golf courses. The area caters to those seeking outdoor adventures and cultural experiences. For a convenient stay, consider Windsor Hills rentals to enhance your trip. With a variety of activities and attractions, Windsor Hills offers something for everyone, making it an ideal destination for fun and relaxation.

  • Walt Disney World® Resort: Experience the magic at one of the world's most famous theme parks, just 7 miles from Windsor Hills. With thrilling rides, enchanting shows, and beloved characters, it offers a perfect family-friendly atmosphere filled with entertainment and joy.
  • Orange County Convention Center: Located 10 miles away, this vibrant arts center showcases a rich tapestry of culture. Attend events, exhibitions, and conventions that highlight diverse artistic expressions in a modern venue, making it a cultural hub in the area.
  • ChampionsGate Golf Club: Just 4 miles from Windsor Hills, this golf course offers a family-friendly environment perfect for excursions. Enjoy beautifully designed courses and the welcoming atmosphere created by friendly staff, making it ideal for both novice and seasoned golfers.

Best time to go to Windsor Hills

The best time to visit Windsor Hills can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Windsor Hills falls in August, when visitor numbers are average and weather is mostly sunny with moderate rain. The coolest average temperature around Windsor Hills falls in January, visitor numbers are slightly high and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January60.6°F (15.9°C)Light RainMostly SunnySlightly HighAverage
February64.4°F (18.0°C)Light RainMostly SunnyAverageAverage
March67.6°F (19.8°C)Light RainMostly SunnySlightly HighSlightly High
April72.7°F (22.6°C)Light RainMostly SunnySlightly HighSlightly High
May77.2°F (25.1°C)Light RainMostly SunnyAverageAverage
June81.1°F (27.3°C)Light RainMostly SunnyAverageAverage
July82.4°F (28.0°C)Moderate RainMostly SunnyAverageAverage
August82.6°F (28.1°C)Moderate RainMostly SunnyAverageSlightly Low
September80.4°F (26.9°C)Moderate RainMostly SunnyAverageSlightly Low
October75.2°F (24.0°C)Light RainMostly SunnySlightly LowAverage
November68.5°F (20.3°C)Light RainMostly SunnySlightly LowSlightly Low
December64.4°F (18.0°C)No RainMostly SunnySlightly LowSlightly High

The nearest major airports for your trip to Windsor Hills

Traveling to Windsor Hills, Florida, is convenient with its proximity to several major airports. Orlando International Airport (MCO) is located 19 miles away, with nearby hotels like The Ritz-Carlton Orlando, Grande Lakes and Rosen Shingle Creek offering various transportation services. Tampa International Airport (TPA) is 62 miles away, featuring hotels such as The Tampa EDITION and JW Marriott Tampa Water Street, both providing easy access. Sarasota-Bradenton International Airport (SRQ) is 87 miles distant, with options like The Ritz-Carlton, Sarasota and Lido Beach Resort nearby. Each airport has accessible transportation services, ensuring a smooth journey to your destination.

Frequently asked questions

What other neighbourhoods are similar to Windsor Hills?
While Windsor Hills is a unique resort community, neighborhoods that offer a similar experience for travelers prioritizing convenience and quality are Reunion Resort and ChampionsGate.

Reunion Resort, located just a short drive from the major theme parks, is known for its spacious vacation homes and a wide array of amenities. It features multiple golf courses, large water parks with lazy rivers, and numerous dining options. This area is particularly well-suited for families seeking an extensive resort experience with plenty of activities on-site, allowing for a relaxed pace between park visits.

ChampionsGate, also conveniently situated near the theme parks, offers a similar blend of vacation rentals and resort-style amenities. It boasts a large clubhouse with a water park, a golf course, and a variety of restaurants and shops.
When is the best time to go to Windsor Hills?
The best time to go to Windsor Hills is during the shoulder seasons of late April to May and late September to November for comfortable weather and fewer crowds.

During these periods, the weather is pleasantly warm, typically ranging from the mid-70s to low 80s Fahrenheit, making it ideal for enjoying theme parks and outdoor activities without the intense heat and humidity of summer. You'll also find that the major attractions are less crowded, which means shorter wait times and a more relaxed experience. This is especially beneficial for families who want to maximize their time at the parks without the stress of peak season crowds.

For those traveling on a budget, visiting in late January or February can offer attractive deals on accommodations and flights, though the weather can be a bit cooler. While this might not be ideal for water park activities, it's superb for exploring the theme parks and other outdoor attractions in comfort.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Windsor Hills.
How much is the nightly rate at a Windsor Hills hotel?
Prices for hotels in Windsor Hills often vary, but you can find a great deal on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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