Windsor Hills Holidays from NZ$2,111

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Top Holiday Package Deals in Windsor Hills

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was NZ$2,876, price is now NZ$2,111 per person
NZ$2,111
per person
23 Jan - 26 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Orlando (MCO)
8.2/10 Very Good! (5,210 reviews)
Room was clean and nice, pool was clean and well maintained. We were served for breakfast a scoop of powdered, watery eggs and 3 cold tater tots. Bread served were cheap dinner rolls. Coffee and liquid creamer were both watery and flavorless. We went out for a real breakfast for the rest of our stay.

Reviewed on 9 Nov 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was NZ$2,901, price is now NZ$2,378 per person
NZ$2,378
per person
23 Jan - 26 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Orlando (MCO)
9.6/10 Exceptional! (1,019 reviews)
Yes, great experience! Will book again.

Reviewed on 11 Nov 2025

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was NZ$2,737, price is now NZ$2,252 per person
NZ$2,252
per person
23 Jan - 26 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Orlando (MCO)
9.2/10 Wonderful! (2,167 reviews)
Convenient location for Florida Mall

Reviewed on 11 Nov 2025

Hilton Orlando

Hilton Orlando

4 out of 5
International Drive District
Price was NZ$2,895, price is now NZ$2,495 per person
NZ$2,495
per person
23 Jan - 26 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Orlando (MCO)
8.4/10 Very Good! (1,005 reviews)
Excellent location and friendly staff. Walk to convention center. Clean rooms and great amenities.

Reviewed on 12 Nov 2025

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 NZ$2,591, price is now NZ$2,252 per person
NZ$2,252
per person
23 Jan - 26 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Orlando (MCO)
8.6/10 Excellent! (1,026 reviews)
Very nice and clean room

Reviewed on 11 Nov 2025

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

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
9.8/10 Exceptional! (73 reviews)
10 out of 10 experience! Definitely recommend this stay to everyone looking to visit Orlando. We stayed seven relaxing days. The house was fully equipped with anything and everything you would ever need for a vacation. House is close to parks and resort is super nice and well taken care of. Wendy, ...

Reviewed on 18 Oct 2025

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Villa 7748 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5
2 Bedroom, 2 Bath Condo 2 miles from Disney and 10 miles from Universal studios.

2 Bedroom, 2 Bath Condo 2 miles from Disney and 10 miles from Universal studios.

Kissimmee
9.6/10 Exceptional! (126 reviews)
Although the it was clearly a little older it was well maintained and clean. Kitchen well stocked with utensils/cooking tools. Could use a cheese grater. Appliances all worked great and the unit temperature was easy to maintain. The furniture and beds were comfortable and clean.Be prepared to purchase ...

Reviewed on 2 Oct 2025

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2 Bedroom, 2 Bath Condo 2 miles from Disney and 10 miles from Universal studios.
Our DisneyDreamVilla - minutes to DisneyWorld!!!

Our DisneyDreamVilla - minutes to DisneyWorld!!!

Kissimmee
9.8/10 Exceptional! (208 reviews)
Everything was as listed. Beautiful home with plenty of space for a family of 5 and room to spare. The home was spotless and well taken care of. We didn’t end up using the resort amenities but the water slides and splash area looked like fun for the kiddos. The pool area was perfect for relaxing ...

Reviewed on 6 Nov 2025

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Our DisneyDreamVilla - minutes to DisneyWorld!!!
See all 1,822 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$2,111. 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

Universal Orlando Resort

Universal Orlando Resort Theme Park Tickets

NZ$359
per adult
92% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Aquatica Orlando

Aquatica Orlando

NZ$93
per traveller
82% of travellers recommend
Aquatica Orlando
Walt Disney World® Resort Theme Park Tickets

Walt Disney World® Resort Theme Park Tickets

NZ$309
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.