Windsor Hills Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Windsor Hills

Price found within the past 48 hours. Click for updated prices.
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Price was CA $1,094, price is now CA $555 per person
CA $555
per person
May 17 - May 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (1,008 reviews)
Room is not dark enough to sleep well

Reviewed on Feb 28, 2026

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was CA $1,247, price is now CA $597 per person
CA $597
per person
Apr 5 - Apr 10
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
8/10 Very Good! (1,367 reviews)
The place is very big with a lot of activities for the children, however my family and I stayed for 5 days and not one day did staff come to clean the room. There was no clean lien or towels, I had to find someone to ask for clean towels and rags daily. I also had to empty my own trash each day.

Reviewed on Mar 3, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $1,334, price is now CA $699 per person
CA $699
per person
Apr 5 - Apr 10
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
8.2/10 Very Good! (5,482 reviews)
It was a quick turnaround trip, did not use amenities, however, property and room was nice and clean.

Reviewed on Mar 2, 2026

The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Price was CA $2,940, price is now CA $1,607 per person
CA $1,607
per person
Apr 11 - Apr 18
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
9/10 Wonderful! (1,748 reviews)
Ocean view....Room was great....service excellent....Motorcycle parking. Can't wait to go back.

Reviewed on Mar 2, 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 showing landscape views

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.

Find hotels in International Drive District

Windsor Hills Hotel Deals

Windsor Hills Condo w/all things Mickey. Pool/Waterpark and minutes from Disney!

Windsor Hills Condo w/all things Mickey. Pool/Waterpark and minutes from Disney!

Kissimmee FL
9.6/10 Exceptional! (29 reviews)
Great spot and nice for a family to book for a disney adventure. Good communication and no issues.

Reviewed on Feb 10, 2026

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Windsor Hills Condo w/all things Mickey. Pool/Waterpark and minutes from Disney!
Villa 7748 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5

Villa 7748 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5

Kissimmee FL
10/10 Exceptional! (81 reviews)
Great location, clean, spacious and quick response time!! We stayed here purposefully looking for off Disney property but still close enough to make it easier to get to the parks. The space was plentiful, heated pool/hot tub and arcade games were our girls favorite things. The themed rooms were magical ...

Reviewed on Feb 14, 2026

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Villa 7748 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5
6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ

6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ

Kissimmee FL
9.4/10 Exceptional! (254 reviews)
Host was very attentive. House was perfect for our family of 11. Close to allnthe parks.

Reviewed on Feb 21, 2026

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6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
See all 1,921 properties in Windsor Hills
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Windsor Hills vacation package cost?
Explore the best of Windsor Hills from just CA $555. Choose from a great selection of rental cars, hotels and flights to suit your travel style. You can score even more discounts when you add a few tours or activities to your package.
How do I get a cheap travel package to Windsor Hills?
Our Windsor Hills vacation packages promise plenty of savings for the savvy wanderer. For the best deals, simply combine your flights, hotels and extras (such as activities) into an affordable package. But great bargains are just the beginning of your next awesome adventure. Book with Expedia and you'll have more than 550 air carriers and 1,000,000 hotels worldwide to choose from. Whatever your budget or style, there's a package here just for you.
Where should I stay in Windsor Hills?
If you hope to check out Orange Lake Golf, skip commuting and stay nearby. It's one of the best attractions in this neighborhood.
What are the top hotels in Windsor Hills?
If this will be your first time in Windsor Hills, make a reservation at Luxury 6 Bedroom 4 Bath Villa With South Facing Pool 10 Minutes From Disney or Windsor Hills Villa With Themed Bedrooms 2mi To Disney. Both hotels offer comfy beds and are popular options with lots of travelers.
How far in advance should I book my Windsor Hills vacation?
It can be hard to know when the best time is to book your Windsor Hills trip. But usually the earlier you book, the cheaper the prices. In some cases, you can lock in your flights and hotels nearly a year prior to your departure date. If you're thinking of a last-minute getaway, no need to worry! There are great bargains posted on Expedia every day.
What does an Expedia Windsor Hills travel package include?
You can select from any combination of hotels, flights and rental cars. Once you've made your booking, you can add some experiences and activities. Want to pick your airfare class? That's easily done too. The choice is all yours when it comes to arranging your perfect Windsor Hills trip.
What should I know before booking a Windsor Hills travel package?
A travel package can be customized for your circumstances and is a great way to make your hard-earned dollars stretch further. How little or much you include is completely up to you. Rental cars, hotels and flights — come up with a combination that suits your plans.
Can I choose my airline with a Windsor Hills Expedia vacation package?
Yes, of course. We have more than 550 partner airlines across the globe, so select the carrier that fits your budget and traveling style.
If I'm not able to travel, can I cancel my Windsor Hills vacation package?
Yes, you can. We understand that even the best-laid plans can fail, so we're here to help if you need to make changes to your Windsor Hills vacation package. It may be possible to cancel or change your itinerary at no cost if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, check your itinerary for the nitty-gritty on change fees.

Discover the most popular places to visit in Windsor Hills

Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(226 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.

Walt Disney World® Resort
Universal Studios Florida™

Universal Studios Florida

4.5/5(988 reviews)

Movie sets and thrill rides combine to create this internationally acclaimed theme park.

Universal Studios Florida
Universal Studios Orlando which includes street scenes, a city and rides

Universal Orlando Resort

4.5/5(399 reviews)

Make your Florida vacation one to remember with a stay at this hotel and theme park complex.

Universal Orlando Resort

Things to do

Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets (US & Canada)

CA $237
per adult
86% of travellers recommend
Universal Orlando Resort Theme Park Tickets (US & Canada)
I-RIDE Trolley Pass

I-RIDE Trolley Pass

CA $15
per traveller
86% of travellers recommend
I-RIDE Trolley Pass
"Drawn to Life" presented by Cirque du Soleil and Disney

Drawn to Life presented by Cirque du Soleil and Disney

CA $116
per adult
98% of travellers recommend
Drawn to Life presented by Cirque du Soleil and Disney
See all activities in Orlando
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.