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
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

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! (79 reviews)
This home was perfect for our Disney vacation! The weather was cooler but the kids were still able to swim due to the heated pool. The game room was perfect and provided a lot of excitement upon arrival. After coming back from a long day at the park, it was nice that everyone had their own space ...

Reviewed on 20 Jan 2026

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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! (28 reviews)
nice place, neat and close to everything we needed. Great kids room. Would recommend and would stay again.

Reviewed on 19 Jan 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
9.2/10 Wonderful! (235 reviews)
Everything was as advertised

Reviewed on 2 Jan 2026

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6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
See all 1,914 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

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)

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

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

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

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

NZ$46
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Universal Orlando Resort

Universal Orlando Resort Theme Park Tickets

NZ$345
per adult
92% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Aquatica Orlando

Aquatica Orlando

NZ$89
per traveller
84% of travellers recommend
Aquatica Orlando
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.