Windsor Hills Holidays from AU$895

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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.
Bluegreen Vacations Fountains, an Ascend Collection Resort

Bluegreen Vacations Fountains, an Ascend Collection Resort

4 out of 5
International Drive District
Price was AU$1,097, price is now AU$895 per person
AU$895
per person
16 Apr - 19 Apr
found 11 hours ago
Return direct flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (1,005 reviews)
We really loved the pool! The room was really nice especially for the price! The screened in balcony was wonderful! We would stay here again 100% Their food was good too!

Reviewed on 6 Mar 2026

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was AU$1,164, price is now AU$901 per person
AU$901
per person
16 Apr - 19 Apr
found 11 hours ago
Return direct flight included
Boston (BOS) to Orlando (MCO)
9.2/10 Wonderful! (2,513 reviews)
Room was clean. Nice lobby. Pool area could use a bit of a clean up.

Reviewed on 28 Feb 2026

WorldMark Reunion

WorldMark Reunion

4 out of 5
Reunion
Price was AU$1,086, price is now AU$908 per person
AU$908
per person
16 Apr - 19 Apr
found 11 hours ago
Return direct flight included
Boston (BOS) to Orlando (MCO)
9.4/10 Exceptional! (594 reviews)
Place was clean and spacious. Didn’t like the fact checking in they tell you that you must do a time share presentation. I said no where did it state that. They have all your information and continuously call.

Reviewed on 11 Feb 2026

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
Price was AU$1,175, price is now AU$1,017 per person
AU$1,017
per person
16 Apr - 19 Apr
found 11 hours ago
Return direct flight included
Boston (BOS) to Orlando (MCO)
8/10 Very Good! (9,083 reviews)
Definitely recommend clean

Reviewed on 6 Mar 2026

Embassy Suites by Hilton Orlando International Dr Conv Ctr

Embassy Suites by Hilton Orlando International Dr Conv Ctr

3.5 out of 5
International Drive District
Price was AU$1,126, price is now AU$986 per person
AU$986
per person
16 Apr - 19 Apr
found 11 hours ago
Return direct flight included
Boston (BOS) to Orlando (MCO)
8.4/10 Very Good! (1,002 reviews)
Spacious rooms, location was very convenient. Happy hour and swimming pool were awesome!

Reviewed on 24 Feb 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
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

Our pick of the best 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! (30 reviews)
The water slide section of the pool was closed.

Reviewed on 19 Feb 2026

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Windsor Hills Condo w/all things Mickey. Pool/Waterpark and minutes from Disney!
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! (255 reviews)
This place was perfect! Decorated in a Disney theme that got the kids excited, plenty of room to spread out and we adored using the pool on our down days. It checked every box for our 7 person vacation with room to spare and fun to be had.

Reviewed on 5 Mar 2026

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6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear

Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear

Kissimmee FL
10/10 Exceptional! (366 reviews)
We had a very nice stay at the villa. The home was clean, comfortable, and exactly as described. The kitchen was well stocked, and we enjoyed spending time by the pool. There was plenty of space for everyone to relax, both indoors and outside. Overall, a smooth and easy stay, we would definitely ...

Reviewed on 26 Feb 2026

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Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
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.
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Frequently asked questions

How much does a Windsor Hills holiday package cost?
Explore the best of Windsor Hills from just AU$895. 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

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

AU$39
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

AU$114
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Scenic 30 Minute Airboat Tour

Scenic 30 Minute Airboat Tour

AU$105
per adult
100% of travellers recommend
Scenic 30 Minute Airboat Tour
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.