Windsor Hills Vacations

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  • Fountain
    Jul 20 - Jul 26

    Westgate Blue Tree Resort in Lake Buena Vista + Flight

    Orlando
    6 nights
    3.5 star property
    8.6/10 - Excellent (1,002 reviews)
    "Great place to stay close to the parks! We stay there every time we visit Orlando, which is at least 3-4 times a year! Comfortable apartments, clean and well taken care of."
    Reviewed May 27, 2026
    Roundtrip • Tokyo (NRT) - Orlando (MCO)
    NRT - MCO • 1 stop MCO - NRT • 1 stop
    ￥307,550
    ￥248,457
    per traveler
    found 1 day ago
    Westgate Blue Tree Resort in Lake Buena Vista
  • Terrace/patio
    Jul 10 - Jul 18

    The Delaney Hotel + Flight

    South Orange
    8 nights
    3.5 star property
    9.6/10 - Exceptional (1,114 reviews)
    "Very clean and modern. The staff were friendly and efficient. We did also eat in the restaurant which has happy hour from 3:30-6:00pm if you eat at the bar. Lots of apps and drinks on the happy hour menu. The hotel beds were very comfortable and the rain shower is a nice amenity. There was one thing I would mention for light sleepers, the hallway and adjacent room noise could be heard. There was no late night noise, so we slept well."
    Reviewed May 30, 2026
    Roundtrip • Nagoya (NGO) - Orlando (MCO)
    NGO - MCO • 2 stops MCO - NGO • 2 stops
    ￥435,484
    ￥321,128
    per traveler
    found 4 hours ago
    The Delaney Hotel
  • Reception
    Jul 18 - Jul 23

    Seasons Florida Resort + Flight

    Kissimmee
    4 nights
    2.0 star property
    9.0/10 - Wonderful (3,596 reviews)
    "Overall I would say this place is worth what you’re paying for. It being on the less expensive side, I wasn’t expecting much nor did I have high hopes of it being a 10/10. The room was a bit muggy ( I get it’s Florida but the smell of the room was a bit musty ) Also didn’t really like that I had to empty out the dehumidifier since it was full and we wanted to get rid of the uncomfortable damp air. Like I said though it’s cheap and has a pool / also close to Disney if that appeals to you so I..."
    Reviewed May 30, 2026
    Roundtrip • Tokyo (NRT) - Orlando (MCO)
    NRT - MCO • 1 stop MCO - NRT • 1 stop
    ￥404,792
    ￥325,950
    per traveler
    found 1 day ago
    Seasons Florida Resort
  • Outdoor pool, pool umbrellas, sun loungers
    Jul 20 - Jul 26

    Magic Village Yards, Trademark Collection by Wyndham + Flight

    Kissimmee
    6 nights
    4.0 star property
    9.0/10 - Wonderful (1,189 reviews)
    "Great place to stay."
    Reviewed May 5, 2026
    Roundtrip • Tokyo (NRT) - Orlando (MCO)
    NRT - MCO • 1 stop MCO - NRT • 1 stop
    ￥345,826
    ￥285,300
    per traveler
    found 1 day ago
    Magic Village Yards, Trademark Collection by Wyndham
  • View from room
    Jul 18 - Jul 23

    Hilton Orlando Buena Vista Palace - Disney Springs® Area + Flight

    Lake Buena Vista
    4 nights
    4.0 star property
    8.6/10 - Excellent (1,866 reviews)
    "Very accommodating"
    Reviewed May 29, 2026
    Roundtrip • Tokyo (NRT) - Orlando (MCO)
    NRT - MCO • 1 stop MCO - NRT • 1 stop
    ￥435,848
    ￥361,234
    per traveler
    found 1 day ago
    Hilton Orlando Buena Vista Palace - Disney Springs® Area

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

Windsor Hills Hotel Deals

Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community

Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community

Kissimmee FL
9.6/10 Exceptional! (79 reviews)
"You might need to speak to your cleaners. The toilet bowls were not clean despite the “sanitize wrap” on them, the bathroom mirrors had toothpaste or soap scum on them. There were crumbs all over the kitchen floor, the kitchen floor mat was covered with crumbs and food stains, crumbs on the couch, ..."

Reviewed on May 12, 2026

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Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community
2 Miles to Disney - 20 sec Walk to Clubhouse - Private Pool - Free Water Park

2 Miles to Disney - 20 sec Walk to Clubhouse - Private Pool - Free Water Park

Kissimmee FL
9.6/10 Exceptional! (221 reviews)
"We thoroughly enjoyed our stay with our family. The home comfortably accommodated us with enough room for 2 kids and 2 couples. Communication with the host was always quick, helpful, and appreciated. The beds were very comfortable, which made our stay even more relaxing. We especially loved being ..."

Reviewed on May 24, 2026

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2 Miles to Disney - 20 sec Walk to Clubhouse - Private Pool - Free Water Park
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! (83 reviews)
"Family friendly! Arcade room for the kids as well as adults were a definite perk. Enough room for all of us and had all the necessary kitchen tools. We'd stay again"

Reviewed on Apr 25, 2026

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Villa 7748 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5
See all 1,820 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 . 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 vacation 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 neighborhood.
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 travelers.
How far in advance should I book my Windsor Hills vacation?
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 vacation package?
Yes, of course. We have more than 550 partner airlines across the globe, so select the carrier that fits your budget and traveling 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.

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

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

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

Things to do

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

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

￥4,278
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

￥6,044
per traveler
86% of travellers recommend
LEGOLAND® Florida Tickets
Walt Disney World® Resort Theme Park Tickets

Walt Disney World® Resort Theme Park Tickets

￥29,522
per adult
Walt Disney World® Resort Theme Park Tickets
See all activities in Orlando

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.