Windsor Hills Holidays from AU$8,847

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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.
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was AU$9,633, price is now AU$8,847 per person
AU$8,847
per person
5 Mar - 10 Mar
found 15 hours ago
Return flight included
Sydney (SYD) to Orlando (MCO)
8.2/10 Very Good! (5,482 reviews)
Clean room Helpful staff

Reviewed on 19 Jan 2026

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Price was AU$10,731, price is now AU$9,791 per person
AU$9,791
per person
5 Mar - 10 Mar
found 15 hours ago
Return flight included
Sydney (SYD) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)
House could have been a bit cleaner otherwise we enjoyed our stay

Reviewed on 11 Jan 2026

The Ritz-Carlton Orlando, Grande Lakes

The Ritz-Carlton Orlando, Grande Lakes

5 out of 5
Price was AU$13,113, price is now AU$12,462 per person
AU$12,462
per person
5 Mar - 10 Mar
found 15 hours ago
Return flight included
Sydney (SYD) to Orlando (MCO)
9.4/10 Exceptional! (1,005 reviews)
Didn’t get a chance to eat breakfast Val took more than 30 minutes to fetch vehicles. Staff was not friendly atmosphere was loud at all hours of the day. The temperature outside was cold. Didn’t get a chance to go to the pool.

Reviewed on 15 Dec 2025

Club Wyndham Bonnet Creek

Club Wyndham Bonnet Creek

3.5 out of 5
Price was AU$10,041, price is now AU$9,599 per person
AU$9,599
per person
5 Mar - 10 Mar
found 15 hours ago
Return flight included
Sydney (SYD) to Orlando (MCO)
9.2/10 Wonderful! (1,003 reviews)
Loved this resort! We can't wait to go back.

Reviewed on 17 Jan 2026

Universal's Aventura Hotel

Universal's Aventura Hotel

3.5 out of 5
Florida Center
Price was AU$9,835, price is now AU$9,411 per person
AU$9,411
per person
5 Mar - 10 Mar
found 15 hours ago
Return flight included
Sydney (SYD) to Orlando (MCO)
9.4/10 Exceptional! (1,051 reviews)
breakfast was too expensive

Reviewed on 15 Jan 2026

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
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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 FL
9.2/10 Wonderful! (234 reviews)
Everything was as advertised

Reviewed on 2 Jan 2026

Get rates
6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
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
9.8/10 Exceptional! (77 reviews)
Great home with fantastic amenities

Reviewed on 3 Jan 2026

Get rates
Villa 7748 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5
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! (25 reviews)
Perfect place to stay if you are looking to be close to Disney parks. The facility itself offers a lot to do if you decide not to go any where outside. There are a lot of restaurants and shops around within a 2 mile radius so you don’t have to go farther to get anything of need. The unit itself is ...

Reviewed on 28 Dec 2025

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Windsor Hills Condo w/all things Mickey. Pool/Waterpark and minutes from Disney!
See all 1,891 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
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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$8,847. 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

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

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

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$66
per adult
100% of travellers recommend
Scenic 30 Minute Airboat Tour
Walt Disney World® Resort Theme Park Tickets

Walt Disney World® Resort Theme Park Tickets

AU$281
per adult
Walt Disney World® Resort Theme Park Tickets
WonderWorks All Access After Dark

WonderWorks All Access After Dark

AU$41
per traveller
88% 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.