Windsor Hills Holidays from NZ$3,371

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Top Holiday Package Deals in Windsor Hills

Price found within the past 48 hours. Click for updated prices.
Silver Lake Resort

Silver Lake Resort

3.5 out of 5
Price was NZ$4,198, price is now NZ$3,371 per person
NZ$3,371
per person
18 June - 25 June
found 21 hours ago
Return flight included
Wellington (WLG) to Orlando (MCO)
8.4/10 Very Good! (1,270 reviews)
Clean rooms. Comfortable beds. Short distance to Disney parks.

Reviewed on 26 Mar 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was NZ$6,317, price is now NZ$4,152 per person
NZ$4,152
per person
18 June - 25 June
found 21 hours ago
Return flight included
Wellington (WLG) to Orlando (MCO)
9.2/10 Wonderful! (1,008 reviews)
Friendly staff. Great location. Villa was amazing

Reviewed on 28 Mar 2026

Evermore Orlando Resort

Evermore Orlando Resort

4 out of 5
Price was NZ$8,611, price is now NZ$6,440 per person
NZ$6,440
per person
18 June - 25 June
found 21 hours ago
Return flight included
Wellington (WLG) to Orlando (MCO)
9.6/10 Exceptional! (587 reviews)
This was a beautiful resort! It was the first time I truly felt like I was in Cancun. The place is amazing, and the customer service is top-notch. The restaurants were delicious, and everything about the resort made it a great place to relax. Traveling with kids can make relaxing a little harder, but they do have plenty of activities to keep them busy, which we really appreciated. We celebrated my son’s birthday during our stay, and I was hoping they would do something small like a card or acknowledgment, but unfortunately they didn’t—that part was a bit disappointing. Overall, we loved it and would definitely come back!

Reviewed on 28 Mar 2026

Magic Village Yards, Trademark Collection by Wyndham

Magic Village Yards, Trademark Collection by Wyndham

4 out of 5
Price was NZ$5,304, price is now NZ$4,071 per person
NZ$4,071
per person
18 June - 25 June
found 21 hours ago
Return flight included
Wellington (WLG) to Orlando (MCO)
9.2/10 Wonderful! (1,174 reviews)
Good place, spacious units but a little dated. Great proximity to Disney World parks.

Reviewed on 28 Mar 2026

Hilton Orlando Lake Buena Vista - Disney Springs® Area

Hilton Orlando Lake Buena Vista - Disney Springs® Area

4 out of 5
Price was NZ$4,266, price is now NZ$3,416 per person
NZ$3,416
per person
18 June - 25 June
found 21 hours ago
Return flight included
Wellington (WLG) to Orlando (MCO)
8.6/10 Excellent! (1,566 reviews)
Room was dark and dingy and had a musty smell. We had a Disney Spring view room however view was quite poor and was not worth the extra cost.

Reviewed on 27 Mar 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 District

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
10/10 Exceptional! (81 reviews)
Great location, clean, spacious and quick response time!! We stayed here purposefully looking for off Disney property but still close enough to make it easier to get to the parks. The space was plentiful, heated pool/hot tub and arcade games were our girls favorite things. The themed rooms were magical ...

Reviewed on 14 Feb 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! (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!
Steps from Waterpark/Pool. Next to Disney w/ Frozen, Aladdin, Beauty&Beast theme

Steps from Waterpark/Pool. Next to Disney w/ Frozen, Aladdin, Beauty&Beast theme

Kissimmee FL
10/10 Exceptional! (232 reviews)
Absolutely perfect little vacation home… clean and super cute! Our kids loved their rooms and the decor added a special touch for our Disney trip. The owners were very responsive and helpful with all of our questions… would definitely recommend to others and stay here again!

Reviewed on 17 Mar 2026

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Steps from Waterpark/Pool. Next to Disney w/ Frozen, Aladdin, Beauty&Beast theme
See all 1,899 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 NZ$3,371. 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 Orlando Resort

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

NZ$47
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

NZ$66
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets

NZ$434
per adult
92% of travellers recommend
Universal Orlando 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.