Windsor Hills Vacations from $188
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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.
Hilton Orlando
International Drive District
Save 100% on your flight
Price was $427, price is now $188 per person
$188
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.4/10 Very Good! (1,005 reviews)
Nice hotel, but all the added fees and prices kill the enjoyment.
Reviewed on Oct 23, 2025
Westgate Vacation Villas Resort
Price was $580, price is now $246 per person
$246
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (1,696 reviews)
The only thing I didn't like was that my daughter is 7 years old and they didn't let me throw her in the water slices and when they changed staff they did let her.
Reviewed on Oct 26, 2025
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
International Drive District
Price was $1,101, price is now $482 per person
$482
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (148 reviews)
Property was so clean. Staff were friendly. I enjoyed my two night stay!
Reviewed on Oct 27, 2025
Ocean Sands Beach Boutique Inn - 1 Acre Private Beach
Vilano Beach
Price was $530, price is now $234 per person
$234
per person
Jan 9 - Jan 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (589 reviews)
This property is a very good unique experience.
our room was on the 1st floor. It was wonderful to sit just outside our room to see all of the amenities available in the rear of the property and see people coming and going. We will definitely stay there again, when we are in the area. We are from outside of Atlanta.
Reviewed on Oct 27, 2025
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
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.
Windsor Hills Hotel Deals
Villa 7748 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5
Kissimmee
9.8/10 Exceptional! (72 reviews)
My kids have already requested for this to be our vacation home next year!!!! It was a win and we all had so much room for all of us. What an amazing vacation. 5 minutes from Disney, 20 minutes from Universal. We had a blast. The owner was very kind and responsive to a few needs we had, it was a ...
Reviewed on Sep 28, 2025
2 Bedroom, 2 Bath Condo 2 miles from Disney and 10 miles from Universal studios.
Kissimmee
9.6/10 Exceptional! (124 reviews)
Although the it was clearly a little older it was well maintained and clean. Kitchen well stocked with utensils/cooking tools. Could use a cheese grater. Appliances all worked great and the unit temperature was easy to maintain. The furniture and beds were comfortable and clean.Be prepared to purchase ...
Reviewed on Oct 2, 2025
6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
Kissimmee
9.2/10 Wonderful! (227 reviews)
Overall it was a nice experience. My only concern was the carpet stairs.
Reviewed on Oct 5, 2025
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
4.5/5(2,427 reviews)
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
4.5/5(9,273 reviews)
Thrill rides based on your favorite movies create this internationally acclaimed theme park.
Universal Orlando Resort
4.5/5(4,155 reviews)
Make your Florida vacation one to remember with a stay at this hotel and theme park complex.
Things to do
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
$27
per adult
90% of travellers recommend
Universal Orlando Resort Express Passes
$192
per traveler
84% 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
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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.