Windsor Hills Holidays from AU$2,947

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Your Windsor Hills Holiday

Take all the hassle out of planning your next escape with a Windsor Hills holiday package. Take in the sights and sounds of this enticing neighbourhood 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 holiday to Windsor Hills, Expedia will help you get there.

Top Holiday Package Deals in Windsor Hills

Price found within the past 48 hours. Click for updated prices.
Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Price was AU$3,991, price is now AU$2,947 per person
AU$2,947
per person
20 Nov - 25 Nov
found 17 hours ago
Return direct flight included
Sydney (SYD) to Orlando (MCO)
9/10 Wonderful! (1,001 reviews)
Clean cottage. Friendly staff.

Reviewed on 8 Oct 2025

Conrad Orlando at Evermore

Conrad Orlando at Evermore

5 out of 5
Price was AU$6,420, price is now AU$4,618 per person
AU$4,618
per person
25 Dec - 31 Dec
found 17 hours ago
Return flight included
Sydney (SYD) to Orlando (MCO)
9.6/10 Exceptional! (282 reviews)
I loved the cleanliness of the entire property. Staff was very professional and polite.

Reviewed on 5 Oct 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was AU$4,606, price is now AU$3,418 per person
AU$3,418
per person
25 Dec - 31 Dec
found 17 hours ago
Return flight included
Sydney (SYD) to Orlando (MCO)
8.2/10 Very Good! (5,346 reviews)
Free shuttles and close proximity to universal and sea world. Family friendly and a-lot of activities for the entire family. Fire pits, mini golf, bikes, pizza and ice cream all without leaving the property. Adults can enjoy yoga, Starbucks, the pool bar and drafts bar & grill. I would stay again in Orlando.

Reviewed on 12 Oct 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was AU$4,180, price is now AU$3,173 per person
AU$3,173
per person
25 Dec - 31 Dec
found 17 hours ago
Return flight included
Sydney (SYD) to Orlando (MCO)
9.6/10 Exceptional! (1,003 reviews)
Great all around highly recommend ! 🙂

Reviewed on 13 Oct 2025

Evermore Orlando Resort

Evermore Orlando Resort

4 out of 5
Price was AU$5,187, price is now AU$4,005 per person
AU$4,005
per person
20 Nov - 25 Nov
found 18 hours ago
Return direct flight included
Sydney (SYD) to Orlando (MCO)
9.4/10 Exceptional! (436 reviews)
Our family thoroughly enjoyed our stay at Evermore. Everything was spotless and kids loved the activities. The house we rented was much more than we expected, The kitchen was large, bedrooms were large and every bedroom had a large bath. Private heated pool and outdoor area topped things off.

Reviewed on 13 Oct 2025

Our guide on 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
Default Image

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.

Find hotels in International Drive District

Our pick of the best Windsor Hills Hotel Deals

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
9.2/10 Wonderful! (225 reviews)
"Very likely"

Reviewed on 2 Sept 2025

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6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
2 Bedroom, 2 Bath Condo 2 miles from Disney and 10 miles from Universal studios.

2 Bedroom, 2 Bath Condo 2 miles from Disney and 10 miles from Universal studios.

Kissimmee
9.6/10 Exceptional! (124 reviews)
"Great. It was clean. The little water park was perfect for the kids on our off days from Disney. Close to Disney and never had too much trouble with traffic."

Reviewed on 22 Aug 2025

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2 Bedroom, 2 Bath Condo 2 miles from Disney and 10 miles from Universal studios.
Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5

Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5

Kissimmee
9.8/10 Exceptional! (71 reviews)
"Amazing! Had everything you could want to stay occupied and comfortable. Family had an awesome time with the game room, pool & just movie nights after long days at Disney. Can’t wait to stay again!!"

Reviewed on 24 Sept 2025

Get rates
Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5
See all 1,841 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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Windsor Hills holiday package cost?
Explore the best of Windsor Hills from just AU$2,947. 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 holiday 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 neighbourhood.
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 travellers.
How far in advance should I book my Windsor Hills holiday?
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 holiday package?
Yes, of course. We have more than 550 partner airlines across the globe, so select the carrier that fits your budget and travelling style.
If I'm not able to travel, can I cancel my Windsor Hills holiday 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 holiday 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(9 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(48 reviews)

Exhilarating rides and world class film sets are brought together to create this outstanding world-renowned theme park.

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

Universal Orlando Resort

4.5/5(30 reviews)

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

Universal Orlando Resort

Activities

Scenic 30 Minute Airboat Tour

Scenic 30 Minute Airboat Tour

AU$58
per adult
100% of travellers recommend
Scenic 30 Minute Airboat Tour
"Drawn to Life" presented by Cirque du Soleil and Disney

Drawn to Life presented by Cirque du Soleil and Disney

AU$152
per adult
92% of travellers recommend
Drawn to Life presented by Cirque du Soleil and Disney
WonderWorks All Access After Dark

WonderWorks All Access After Dark

AU$42
per traveller
84% of travellers recommend
WonderWorks All Access After Dark
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.