Windsor Hills Vacations
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Your Windsor Hills Vacation
Take all the hassle out of planning your next escape with a Windsor Hills vacation package. Take in the sights and sounds of this enticing neighborhood and experience all it has to offer. Eager to sightsee during your trip to Windsor Hills? Be sure to check out nearby attractions like Mystic Dunes Golf Club, Orange Lake Golf and Jack Nicklaus Course. Stop dreaming and start doing. When it's time to book your dream vacation to Windsor Hills, Expedia will help you get there.
Price found within the past 48 hours. Click for updated prices.
- Palazzo Lakeside Hotel
Aug 5 - Aug 11Palazzo Lakeside Hotel + Flight
Kissimmee6 nights8.2/10 - Very Good (5,136 reviews)"Good"Reviewed May 19, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • 1 stop MCO - EWR • 1 stop - Westgate Palace Hotel / Universal / I-Drive
Jul 2 - Jul 13Westgate Palace Hotel / Universal / I-Drive + Flight
International Drive District11 nights8.8/10 - Excellent (1,253 reviews)"Our room was extremely clean and quiet. It was very close to Universal Studios. Highly recommend!"Reviewed May 16, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • 1 stop MCO - EWR • 1 stop$2,604$1,002found 1 day agoper traveler - Westgate Towers Resort
Jul 21 - Jul 28Westgate Towers Resort + Flight
Kissimmee7 nights8.6/10 - Excellent (1,001 reviews)"Very good place"Reviewed May 18, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • 1 stop MCO - EWR • 1 stop - Westgate Town Center Resort
Jul 21 - Jul 28Westgate Town Center Resort + Flight
Kissimmee7 nights8.2/10 - Very Good (1,732 reviews)"This family friendly resort offers first class amenities and hospitality at a budget friendly price. The accommodations were clean and had everything we needed already there."Reviewed May 18, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • 1 stop MCO - EWR • 1 stop - Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
Aug 1 - Aug 8Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive + Flight
International Drive District7 nights7.8/10 - Good (496 reviews)"The hotel was beautiful and staff were courteous. I’d booked this hotel because I wanted to enjoy the rooftop terrace, but upon arrival was told that I couldn’t because I wasn’t a club member. I was put on the highest floor and within two days both elevators were out of service so all guests had to use the service elevator in that part of the building. I had also booked for the breakfast, but it was over by 9:30 so I never made it. Also, on separate occasions, the power went out in my room thus..."Reviewed May 10, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • Nonstop MCO - EWR • Nonstop
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
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.
Windsor Hills Hotel Deals
6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
Kissimmee FL
9.4/10 Exceptional! (260 reviews)
"My family and I truly enjoyed our stay at this property."
Reviewed on Apr 28, 2026
Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community
Kissimmee FL
9.6/10 Exceptional! (78 reviews)
"The property was just as described, very spacious, clean and fully stocked. Check-in was simple and the Resort’s water park was just what we needed for a fun and enjoyable weekend. There nine people in our group and we had more than enough space to move around. I would definitely recommend this home ..."
Reviewed on Apr 27, 2026
Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills
Kissimmee FL
10/10 Exceptional! (200 reviews)
"Great villa and so close to the parks!! Very well equipped for our family.Absolutely excellent and responsive host, helping out quickly with all our resort and other questions.A great place to stay for a family looking to “theme park”!!"
Reviewed on May 17, 2026
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.
Discover the most popular places to visit in Windsor Hills
Walt Disney World® Resort
Walt Disney World® Resort is part of Orlando. It makes up part of bustling metropolis that is home to 240,000 inhabitants. Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando’s city center. If you are flying in, Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando International Airport.
Universal Studios Florida
Thrill rides based on your favorite movies create this internationally acclaimed theme park.
Universal Orlando Resort
Make your Florida vacation one to remember with a stay at this hotel and theme park complex.
Things to do
Walt Disney World® Resort Disney After Hours
$191
per adult
100% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
$27
per adult
92% of travellers recommend
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- Walt Disney World® Resort
- Disney's Hollywood Studios®
- Orlando Vacations
- Mystic Dunes Golf Club
- Disney's Animal Kingdom® Theme Park
- Bonanza Golf & Gifts
- Mighty Jungle Golf
- Island H2O Live!
- Disney's Maingate West Vacations
- Disney's Blizzard Beach Water Park
- Four Corners Vacations
- Visit Disney's Maingate West
- Central Florida Vacations
- Disney's Winter Summerland Miniature Golf Course
- Espn Wide World of Sports Complex
- Car rental Orlando Airport (MCO)
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- Greenmotion Drive&Go Rental Cars in Disney's Maingate West
- Enterprise Rental Cars in Four Corners
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.