Windsor Hills Holidays

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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.

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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! (23 reviews)
Great location, amazing bedroom for the kids, and all around great place

Reviewed on 5 Nov 2025

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

Magical Harry Potter Themed Condo

3 out of 5
Almaton Loop 2813 Kissimmee FL
8/10 Very Good! (1 review)
Overall a great stay. Other people are loud at night in upstairs condos but that’s to be expected. The pool area was great. The store on property was very helpful and well priced. They also have good pizza. My only complaint would be no storage in kids room. We had 4 kids with no place to put ...

Reviewed on 11 Apr 2025

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Magical Harry Potter Themed Condo
Disney World 2 Miles! Family condo

Disney World 2 Miles! Family condo

Kissimmee FL
The price is NZ$458 per night from 3 Jan to 4 Jan
NZ$458
3 Jan - 4 Jan 2026
includes taxes & fees
8.8/10 Excellent! (35 reviews)
This is our second time staying on this resort (two different units). The property was clean and well maintained. Very safe location!!

Reviewed on 4 Dec 2025

Disney World 2 Miles! Family condo
See all 1,896 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.

Frequently asked questions

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

An attraction popular with visitors from around the world, where you can wander through film sets and enjoy the thrills and spills of the rides.

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

Universal Orlando Resort

Universal Orlando Resort Theme Park Tickets

NZ$392
per adult
92% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Aquatica Orlando

Aquatica Orlando

NZ$92
per traveller
84% of travellers recommend
Aquatica Orlando
Walt Disney World® Resort Theme Park Tickets

Walt Disney World® Resort Theme Park Tickets

NZ$326
per adult
Walt Disney World® Resort Theme Park Tickets
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.