Windsor Hills Holidays

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Price found within the past 48 hours. Click for updated prices.
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Save 100% on your flight
Price was HK$7,134, price is now HK$4,394 per person
HK$4,394
per person
23 Sept - 28 Sept
found 19 hours ago
Return direct flight included
Vancouver (YVR) to Orlando (MCO)
9.6/10 Exceptional! (1,000 reviews)
Everything was great! Would definitely stay again.

Reviewed on 17 Aug 2025

Hilton Orlando

Hilton Orlando

4 out of 5
International Drive District
Price was HK$6,897, price is now HK$4,879 per person
HK$4,879
per person
23 Sept - 28 Sept
found 19 hours ago
Return direct flight included
Vancouver (YVR) to Orlando (MCO)
8.4/10 Very Good! (1,002 reviews)
The Hilton Orlando was comfy as always. Staff was professional and courteous. The only downside is that you have rent microwave but aside from that, my stay was pleasant. I love the store and especially restaurant options. The pool and hot tub were amazing.

Reviewed on 16 Aug 2025

Signia by Hilton Orlando - An Official Walt Disney World® Hotel

Signia by Hilton Orlando - An Official Walt Disney World® Hotel

4 out of 5
Save 100% on your flight
Price was HK$8,934, price is now HK$6,426 per person
HK$6,426
per person
23 Sept - 28 Sept
found 19 hours ago
Return direct flight included
Vancouver (YVR) to Orlando (MCO)
8.8/10 Excellent! (1,011 reviews)
The breakfast the was excellent

Reviewed on 18 Aug 2025

Caribe Royale Orlando

Caribe Royale Orlando

4.5 out of 5
Price was HK$6,201, price is now HK$4,490 per person
HK$4,490
per person
23 Sept - 28 Sept
found 19 hours ago
Return direct flight included
Vancouver (YVR) to Orlando (MCO)
9.2/10 Wonderful! (4,320 reviews)
Our second time at this resort. Looking for to going again. Resort is well maintained and all of the staff are super attentive.

Reviewed on 18 Aug 2025

The Eo Inn - Downtown

The Eo Inn - Downtown

3 out of 5
South Eola
Price was HK$6,069, price is now HK$4,433 per person
HK$4,433
per person
23 Sept - 28 Sept
found 19 hours ago
Return direct flight included
Vancouver (YVR) to Orlando (MCO)
8/10 Very Good! (1,005 reviews)
Quaint and unique property, very convenient near the Lake and restaurants in the area. Beds were comfortable, shower worked well, and although the room overall nicely refurbished it showed age on door edges (bathroom door warped and wouldn't fully close), carpet in room and hallways felt dirty. Free continental breakfast had a good variety of options, nice to have multiple water bottles. The building had network problems at night and we couldn't use the TV, but that can happen with storms. Staff was pleasant, good service but not stand out.

Reviewed on 19 Aug 2025

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

Top hotels in Windsor Hills

Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5

Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5

Kissimmee
9.8/10 Exceptional! (67 reviews)
"The Home was wonderful for our two Families. Clean, Spacious to accommodate everyone. Pool and Spa got a definite workout from the kids and myself. Communications with Property Management was on-point. 3 things beed addressed: *a Lil bit of Algie cleaning to the Spa"

Reviewed on 29 Jul 2025

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Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5
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
9.2/10 Wonderful! (221 reviews)
"Beautiful home and neighborhood"

Reviewed on 24 Jul 2025

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6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
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
9.4/10 Exceptional! (15 reviews)
"We will for sure be staying again! Amazing place amazing condo and property manager! My kids had a blast. I loved that they had water park areas for multiple ages and pool was terrific very relaxing with littles and big kids park playground castle theme was cute! family friendly with activities for ..."

Reviewed on 16 Jul 2025

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Windsor Hills Condo w/all things Mickey. Pool/Waterpark and minutes from Disney!
See all 1,788 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 vacation package cost?
Explore the best of Windsor Hills from just HK$4,394. 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 vacation 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 vacation 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.

Popular places to visit

Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(63 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(273 reviews)

Movie sets and thrill rides combine to create this internationally acclaimed theme park.

Universal Studios Florida
Universal Studios Orlando showing rides, a city and street scenes

Universal Orlando Resort

4.5/5(166 reviews)

Make your Florida vacation one to remember with a stay at this hotel and theme park complex.

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Things to do

Aquatica Orlando

Aquatica Orlando

HK$380
per traveller
82% of travellers recommend
Aquatica Orlando
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

HK$521
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Indoor Karting

Andretti Indoor Karting & Games in Orlando

HK$242
per adult
80% of travellers recommend
Andretti Indoor Karting & Games in 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.