Windsor Hills Vacations from $248
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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 River Ranch Resort & Rodeo
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (354 reviews)
Nice place. Kids had a good time. Not encouraged to go there if you are a minority. You wont feel welcomed. The staff is great, but the type of people that go there arent really folks that likely share the same interests as you do. There are Confederate flags all over; etc. Hotel rooms are no bueno, old. IF you want something nice, you need to spend the money glamping or have your own trailer.
Reviewed on Jun 24, 2025
Westgate Palace Hotel / Universal / I-Drive
International Drive
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
I really loved our stay my kids are older so the convenience of two rooms were great. The view was amazing we were given a free upgrade to a deluxe suite. We only stayed 3 days, so we didn’t get to utilize everything.my only take ways was the hit water and lack of water pressure.
Reviewed on Jul 7, 2025
Ocean Sands Beach Boutique Inn - 1 Acre Private Beach
Vilano Beach
Save 100% on your flight
per person
Sep 10 - Sep 15
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.6/10 Excellent! (540 reviews)
Nice Beach across the road, Very nice staff!
Reviewed on Jul 6, 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
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
6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
Kissimmee
9.2/10 Wonderful! (214 reviews)
Spacious
"The house is very spacious. It has some very good pros and some cons.Pros- Spacious with plenty of room for our party of 12. Nice size kitchen, the bedrooms were good size as was the bathrooms. Comfortable beds and in a very convenient location to all the Disney Parks.Cons- The garage converted to ..."
Reviewed on Jun 1, 2025
Magical 4 Bedroom Villa with Private Pool Minutes from Disney! Free Pool Heat!
Kissimmee
9.8/10 Exceptional! (136 reviews)
Epic family fun
"My wife and kids had an absolute blast in this property. Beautiful resort with a water park and so much more. We had a great time. Thank you."
Reviewed on Jun 27, 2025
2Pool Home Water Park Disney 2 m Universal Sea World! By Mystic Dunes golf !
Kissimmee
9.4/10 Exceptional! (10 reviews)
Very Nice
"Would definitely stay again"
Reviewed on May 6, 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
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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.