Windsor Hills Vacations from $320
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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.
The Latest Windsor Hills Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Westgate Towers Resort
Save 100% on your flight
Price was $571, price is now $320 per person
$320
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Orlando (MCO)
8.6/10 Excellent! (1,021 reviews)
Very clean, nice pools, very central location for everything in orlando. I hidden gem actually. We had one of the refurbed rooms. Helpful staff.
Reviewed on May 16, 2026
Westgate Palace Hotel / Universal / I-Drive
International Drive District
Price was $1,214, price is now $504 per person
$504
per person
Jul 9 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (1,254 reviews)
Our room was extremely clean and quiet. It was very close to Universal Studios. Highly recommend!
Reviewed on May 16, 2026
Westgate Town Center Resort
Save 100% on your flight
Price was $1,036, price is now $568 per person
$568
per person
Jul 21 - Jul 28
found 9 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (1,718 reviews)
The property and amenities were top notch!
Reviewed on May 15, 2026
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Save 100% on your flight
Price was $1,427, price is now $858 per person
$858
per person
Jul 19 - Jul 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.2/10 Wonderful! (1,011 reviews)
Loved the clean lesson the space. Loved how close o was to the pool and how friendly everyone was. Definitely 10/10
Reviewed on May 16, 2026
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
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- Island H2O Live!
- Disney's Maingate West Vacations
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- Espn Wide World of Sports Complex
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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.