Find hotels in Windsor Hills, Orlando from $55

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Discover 1,793 Windsor Hills hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Our top choices for Windsor Hills hotels

Rosen Shingle Creek

4.5 star property
9.4 out of 10, Exceptional, (4000)
"Great stay!"
$88 nightly
The price is $100
Sep 7 - Sep 8
Total with taxes and fees
Rosen Shingle Creek

Palazzo Lakeside Hotel

3.0 star property
8.2 out of 10, Very Good, (5189)
"Nice to stay with family and breakfast was perfect "
$69 nightly
The price is $78
Sep 3 - Sep 4
Total with taxes and fees
Palazzo Lakeside Hotel

Hilton Garden Inn Orlando I-4 Millenia Blvd Mall

3.0 star property
9.0 out of 10, Wonderful, (368)
"Very nice place to stay totally recommended "
$101 nightly
The price is $114
Sep 7 - Sep 8
Total with taxes and fees
Hilton Garden Inn Orlando I-4 Millenia Blvd Mall

Mickey s Hideaway Windsor Hills Resort

2.0 star property
$370 nightly
The price is $420
Sep 13 - Sep 14
Total with taxes and fees
Mickey s Hideaway Windsor Hills Resort

Windsor Hills Getaway 3BR with Pool

3.0 star property
$2,000 nightly
The price is $2,270
Sep 3 - Sep 4
Total with taxes and fees
Windsor Hills Getaway 3BR with Pool

Ramada by Wyndham Hotel & Water Park

3.0 star property
7.2 out of 10, Good, (1470)
"Excellent place for familys"
$68 nightly
The price is $77
Sep 3 - Sep 4
Total with taxes and fees
Ramada by Wyndham Hotel & Water Park

Lake Nona Wave Hotel

4.0 star property
9.6 out of 10, Exceptional, (1011)
"Great hotel "
$189 nightly
The price is $212
Sep 16 - Sep 17
Total with taxes and fees
Lake Nona Wave Hotel

Magic Moment Resort and Kids Club

3.0 star property
8.4 out of 10, Very Good, (2490)
"Good place to stay with kids and clean"
$57 nightly
The price is $64
Sep 4 - Sep 5
Total with taxes and fees
Magic Moment Resort and Kids Club

Sonesta Essential Orlando

3.0 star property
7.2 out of 10, Good, (1711)
"Nice place, very friendly staff and a nice breakfast"
$81 nightly
The price is $90
Sep 3 - Sep 4
Total with taxes and fees
Sonesta Essential Orlando

Margaritaville Resort Orlando with H2O Waterpark

4.0 star property
9.0 out of 10, Wonderful, (3592)
"Great place to stay."
$175 nightly
The price is $199
Sep 28 - Sep 29
Total with taxes and fees
Margaritaville Resort Orlando with H2O Waterpark

Seasons Florida Resort

2.0 star property
8.8 out of 10, Excellent, (3086)
"We love staying here "
$48 nightly
The price is $55
Oct 2 - Oct 3
Total with taxes and fees
Seasons Florida Resort

Rosen Centre Hotel

4.0 star property
9.0 out of 10, Wonderful, (3928)
"Perfect stay close to the parks."
$81 nightly
The price is $91
Sep 11 - Sep 12
Total with taxes and fees
Rosen Centre Hotel

Pestana Orlando Suites - Lake Buena Vista

4.0 star property
9.4 out of 10, Exceptional, (1755)
"Good place prefect for short stay"
$88 nightly
The price is $99
Sep 3 - Sep 4
Total with taxes and fees
Pestana Orlando Suites - Lake Buena Vista

Meliá Orlando Celebration

4.0 star property
8.6 out of 10, Excellent, (1536)
"Have stayed here couple times. Overall a very nice place and location is perfect."
$104 nightly
The price is $118
Sep 10 - Sep 11
Total with taxes and fees
Meliá Orlando Celebration

Wyndham Lake Buena Vista – Disney Springs® Area

4.0 star property
8.8 out of 10, Excellent, (2731)
"Love this place, stay here often!"
$119 nightly
The price is $134
Sep 3 - Sep 4
Total with taxes and fees
Wyndham Lake Buena Vista – Disney Springs® Area

Kompose Boutique Resort at Theme Parks

3.0 star property
9.4 out of 10, Exceptional, (1176)
"Great stay"
$75 nightly
The price is $85
Sep 7 - Sep 8
Total with taxes and fees
Kompose Boutique Resort at Theme Parks

Hyatt House Orlando International Drive

4.0 star property
9.2 out of 10, Wonderful, (932)
"We enjoyed our stay at "
$103 nightly
The price is $116
Sep 21 - Sep 22
Total with taxes and fees
Hyatt House Orlando International Drive

SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

3.0 star property
8.6 out of 10, Excellent, (3257)
"Love this hotel "
$71 nightly
The price is $80
Sep 22 - Sep 23
Total with taxes and fees
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

Wyndham Garden Orlando Airport

3.0 star property
9.0 out of 10, Wonderful, (3826)
"Great place to stay."
$84 nightly
The price is $95
Sep 3 - Sep 4
Total with taxes and fees
Wyndham Garden Orlando Airport

Red Lion Hotel Orlando Lake Buena Vista South

3.5 star property
8.8 out of 10, Excellent, (4072)
"Excellent hotel and staff."
$80 nightly
The price is $91
Sep 9 - Sep 10
Total with taxes and fees
Red Lion Hotel Orlando Lake Buena Vista South
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

International Drive District

1 out of top 10 points of interest in this area

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

Bay Lake

4 out of top 10 points of interest in this area

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.

Downtown Orlando

Orlando's historic core boasts art galleries, retail, restaurants, and nightclubs, with attractions like Lake Eola Park, Linton E. Allen Memorial Fountain, and performing arts theaters, all accessible via public transportation.

Florida Center

2 out of top 10 points of interest in this area

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

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

Find out more about Windsor Hills

Top reasons to visit Windsor Hills

  • Proximity to Theme Parks: Windsor Hills is just minutes away from popular attractions like Walt Disney World and Universal Studios, perfect for family fun.
  • Family-Friendly Accommodations: The area offers a range of themed villas and homes, catering to families and groups of all sizes.
  • Water Park Access: Enjoy the on-site Windsor Hills Water Park, a fantastic way to cool off and have fun.
  • Outdoor Adventures: Explore scenic lakes and golf courses, ideal for outdoor enthusiasts.
  • Relaxation and Shopping: Experience a blend of relaxation at the resort and shopping options for a delightful day out.

Find great hotels near Windsor Hills

Discover the charm of Windsor Hills, a family-friendly resort destination in Four Corners, Florida. With a variety of accommodations, including luxurious villas and pet-friendly options, it's the perfect spot for a romantic getaway or a fun-filled family vacation. Whether you're looking for a relaxing retreat or easy access to Orlando's attractions, Windsor Hills has something for everyone, ensuring an unforgettable stay in the heart of Central Florida.

  • Hilton Vacation Club Aqua Sol Orlando West: Experience a vibrant family-friendly atmosphere at Hilton Vacation Club Aqua Sol Orlando West, located 4 miles from Windsor Hills. This 3.5-star hotel is perfect for families and LGBTQIA travelers, offering a welcoming environment for all. The property features a variety of amenities for children, including a fun-filled Water Park, an on-site Mini Golf course, and an Arcade Game Room. With a shared playground for kids and a dedicated children's pool, families can enjoy a delightful vacation while making unforgettable memories.
  • Hilton Vacation Club Mystic Dunes Orlando: Nestled just 0.5 miles from Windsor Hills, Hilton Vacation Club Mystic Dunes Orlando is a 3.5-star hotel that caters to families and golf enthusiasts alike. This property invites guests to indulge in a golf-themed experience, complete with scenic golf courses. Children can enjoy a range of engaging activities, from Foosball and Ping Pong tables to a selection of books designed for young readers. With a dedicated children's pool, this hotel ensures fun and relaxation for guests of all ages in a beautifully landscaped setting.
  • Walt Disney World Dolphin: Situated 4 miles from Windsor Hills, the 4-star Walt Disney World Dolphin offers a sophisticated blend of business and leisure amenities. This hotel is LGBTQIA welcoming and ideal for business travelers, featuring accessible meeting rooms, conference space, and a fully equipped business center. Additionally, golf enthusiasts can enjoy the nearby golf courses. With its prime location and extensive amenities, the Walt Disney World Dolphin stands out as a top choice for those seeking a balanced vacation experience that caters to both work and play.

Where to stay near Windsor Hills

Windsor Hills is the perfect family vacation destination, offering a blend of relaxation and excitement. Nestled near Orlando, this neighborhood features family-friendly homes and themed accommodations, including Disney-themed bedrooms. Explore nearby attractions like Walt Disney World, Universal Studios, and other Orlando gems. With its friendly atmosphere and diverse recreational activities, Windsor Hills provides a memorable experience for families seeking adventure and relaxation in the heart of Florida.

  • Orlando: Orlando is a bustling metropolis and a major tourist destination, home to iconic theme parks and entertainment venues. Located in the heart of Central Florida, it offers a vibrant mix of attractions ranging from the world-famous Walt Disney World to Universal Studios. Visitors flock to Orlando throughout the year, with peak seasons occurring in March, July, and December. Enjoy outdoor activities, shopping at local malls, and exploring the city's rich arts scene. With its diverse dining options and proximity to beautiful beaches, Orlando ensures a fun-filled vacation for families and adventure seekers alike.
  • Four Corners: Nestled in the Four Corners area, this charming village is a gateway to numerous attractions. It is conveniently located near several major theme parks, making it an ideal spot for families seeking entertainment and adventure. The village sees a spike in visitor numbers during February to March and July, offering a lively atmosphere. Four Corners is also known for its golf courses and proximity to resorts, providing ample opportunities for relaxation and leisure. Whether you're teeing off or enjoying a day at a local theme park, Four Corners offers a delightful mix of activities for all ages.
  • Crestwynd Bay: Just 0.3 miles from Windsor Hills, Crestwynd Bay is a welcoming neighborhood perfect for families and travelers looking for fun. With a blend of resorts, shopping areas, and golf courses, it offers a variety of activities to suit every interest. Peak travel times align with those of Orlando, with busy months in March, July, and December. The neighborhood's close proximity to major attractions like theme parks and film studios makes it a strategic base for exploring the wonders of Florida. Crestwynd Bay invites visitors to experience its local charm while enjoying the excitement of nearby adventures.

Things to do near Windsor Hills

Windsor Hills is perfect for family-friendly vacations, offering a variety of activities and attractions. Visitors can enjoy nearby theme parks, play golf at beautiful courses, and indulge in outdoor adventures. The area also features a resort for relaxation and shopping options for a fun day out. Don't miss the chance to experience exciting waterpark access and the comforts of a golf villa during your stay.

Shopping

For a great shopping experience, visit Disney Springs™, just 6 miles from Windsor Hills, offering a vibrant mix of shops. Old Town, 5 miles away, features entertainment and unique stores. Don't miss the 192 Flea Market, located 9 miles away, for local finds and treasures.

Recreation

Experience the excitement at ESPN Wide World of Sports Complex, just 3 miles from Windsor Hills, perfect for sports enthusiasts. Enjoy a round of golf at Mystic Dunes Golf Club, only 0.7 miles away, or unwind in the serene Northeast Regional Park, located 4 miles away, ideal for relaxation.

Adventure

Experience the thrill at Disney's Typhoon Lagoon Water Park, a fantastic waterpark 5 miles from Windsor Hills, featuring exciting rides and family fun. For karting enthusiasts, Kissimmee Go-Karts, located 8 miles away, offers an adrenaline-pumping adventure. Explore nature on the scenic Blue Lake trail, 10 miles from your stay.

Nightlife

In Windsor Hills, Medieval Times offers a unique blend of culture and entertainment with its captivating dinner theater, just 8 miles away. For adventure seekers, Wonderworks and Splitsville Luxury Lanes & Dinner Lounge provide thrilling arcade experiences, both within 11 and 6 miles, respectively.

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

Booking tips and Expedia advantages for Windsor Hills

To save money on your trip to Windsor Hills, consider visiting during the cheaper months of August, September, or November. Booking your hotel about a month in advance can yield better rates, especially on Tuesdays when prices drop. Check Expedia for last-minute deals and package options that combine flights and accommodations for added savings. Utilize the price filter to find budget-friendly stays, and join Expedia’s One Key membership for exclusive discounts and cash rewards for future bookings. Explore free local attractions to maximize your vacation experience without overspending.

  • 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: The cheapest time to book a hotel around Windsor Hills is usually 1 month out from when you are planning to stay. If you're a little more spontaneous, you could also peruse Expedia's last minute deals which could secure you a cheaper stay. Look out for the green banner below the price to spot the deals.
  • 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: Utilize Expedia’s search tool to refine your options based on your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified filter will showcase hotels that are sustainable and environmentally friendly. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • 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.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Windsor Hills

Windsor Hills is perfect for families seeking outdoor entertainment and adventure. This vibrant area features exciting attractions like theme parks, scenic lakes, and golf courses. Visitors can enjoy the Windsor Hills Water Park and take a magical trip to Disney, ensuring a memorable vacation experience filled with fun and relaxation for everyone.

  • Walt Disney World® Resort: Experience the magic at this iconic theme park, just 7 miles from Windsor Hills. With thrilling rides, enchanting shows, and beloved Disney characters, it's a dream destination for families and entertainment enthusiasts alike.
  • Orange County Convention Center: Located 10 miles away, this arts center is a cultural hub featuring various exhibitions and events. Immerse yourself in diverse art forms and enjoy the vibrant atmosphere that celebrates creativity.
  • ChampionsGate Golf Club: Just 4 miles from your stay, this golf course accommodation offers a family-friendly environment. Enjoy a round of golf, relax in beautiful surroundings, and experience the warm hospitality of friendly staff.

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

To visit Windsor Hills, you can fly into two major airports. Orlando International Airport (MCO) is located 19 miles away, with nearby hotel options such as The Ritz-Carlton Orlando, Grande Lakes, and Hyatt Regency Orlando, both offering convenient shuttle services. Kissimmee Gateway Airport (ISM) is another option, situated 10 miles from Windsor Hills, with excellent hotels like Waldorf Astoria Orlando and Encore Resort and Water Park At Reunion by Rentyl, providing transfers and shuttles for easy access. Both airports ensure a smooth start to your vacation in the sunny state of Florida.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What are the best family hotels in Windsor Hills?
Windsor Hills Getaway 3BR with Pool is a fantastic choice for families seeking comfort and convenience in Kissimmee, Florida. This spacious three-bedroom property not only provides a private pool—superb for splashing around after a day at the nearby theme parks—but also features a fully equipped kitchen. This amenity allows families to prepare their own meals, offering flexibility and the chance to save on dining costs while enjoying home-cooked favorites.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Windsor Hills hotel for you.
How can I save on a Windsor Hills hotel booking with Expedia?
One Key™ - Expedia's free travel rewards program - gives you instant access to perks and Member Prices on Windsor Hills hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings.

*OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Windsor Hills hotel?
Hotel prices in Windsor Hills often vary, but you can find a great deal from $55 on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.