Windsor Hills Vacations

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Your Windsor Hills Vacation

Reserving a tailor-made Windsor Hills vacation package is a good way to get to know this unique neighborhood. From its must-visit places to its little-known gems, you won't be short of new adventures. Eager to explore the sights during your trip to Windsor Hills? Make sure you stop by nearby attractions like Mystic Dunes Golf Club, Orange Lake Golf and Jack Nicklaus Course. Expedia is here to put your plans into action. Book your ideal Windsor Hills vacation now.

The Latest Windsor Hills Vacation Packages

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

Palazzo Lakeside Hotel

3 out of 5
Save 100% on your flight
per person
Jul 1 - Jul 5
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8/10 Very Good! (3,921 reviews)
This was my second time staying at this property. Every interaction with front desk was phenomenal. The functionality of the room was well thought out. The cleanliness was superior. Everything worked as it should. Loved the extra large Roku tv inside the room. Beds were nice and comfy. Super love that the deposit was only $50. Reasonable and realistic. My only suggestion would be to add an extra top lock for the doors that children can not reach. My daughter ran out the room while I was mid shower. A peephole for the door would be nice also. The playground area was nice, not too many options, one was broken and many had spider webs. My daughter enjoyed it and stayed a while. The hammocks were clean and comfortable. The dock was romantic and inviting. Absolutely loved the scriptures planted around the hotel. My favorite part. 10/10 would love to stay again. Oh and breakfast was top tier. The healthy options were fantastic. Very filling and delectable. Would highly recommend.

Reviewed on May 11, 2024

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
per person
Jul 1 - Jul 5
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.4/10 Very Good! (1,003 reviews)
The front desk staff was awesome

Reviewed on May 12, 2024

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
per person
Jul 1 - Jul 5
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
7.8/10 Good! (3,697 reviews)
Loved this for my Wdw trip

Reviewed on May 13, 2024

Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Save 100% on your flight
per person
Jun 13 - Jun 17
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (825 reviews)
Customer service was excellent

Reviewed on May 12, 2024

Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
per person
Jul 31 - Aug 5
Roundtrip non-stop flight included
New York (LGA) to Orlando (MCO)
8.4/10 Very Good! (1,001 reviews)
Love this property and would recommend it to family and friends

Reviewed on May 12, 2024

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
Universal Studios Orlando featuring signage, a city and night scenes

Florida Center

2 out of top 10 points of interest in this area

While visiting Florida Center, you might make a stop by sights like Universal Orlando Resort and Universal Studios Florida.

Find hotel + flight trips in Florida Center

Windsor Hills Hotel Deals

Vibrant Townhome near parks!
Vibrant Townhome near parks!
Kissimmee
9.6/10 Exceptional! (5 reviews)
Love the resort!!!
"The condo was as described and was exactly what we needed for the week!! The overall cleanliness of the condo was just ok, the pool and pool area could use some TLC. There were small mite bugs but only in the kitchen area. The resort and the location of the condo was perfect. The beds were very comfy!! ..."

Reviewed on Oct 15, 2023

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Vibrant Townhome near parks!
Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills
Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills
Kissimmee
9.8/10 Exceptional! (111 reviews)
Incredible in every way!
"All of the other reviews sold us on staying here, and once we arrived, we were not let down. Upon arrival, check-in was very easy and what was really remarkable is the house is very, very clean. Furthermore, everything you would need to support a family is already at the house. Prior to arrival, ..."

Reviewed on May 6, 2024

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Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills
Water Park & Fantastic Pool only Minutes To Walt Disney World's Front Gate!!!
Water Park & Fantastic Pool only Minutes To Walt Disney World's Front Gate!!!
Kissimmee
9.6/10 Exceptional! (165 reviews)
Beautiful place. Great Location.
"The place was beautiful. The location was great. The host was easy to communicate with and very accommodating. The Disney themed art was a great touch as well. Hope to be fortunate enough to stay there again."

Reviewed on May 7, 2024

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Water Park & Fantastic Pool only Minutes To Walt Disney World's Front Gate!!!
See all 1,950 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Windsor Hills vacation package cost?
Explore the best of Windsor Hills from just $266. 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

Image for Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(2,427 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
Image for Universal Studios Florida

Universal Studios Florida

4.5/5(9,273 reviews)

Thrill rides based on your favorite movies create this internationally acclaimed theme park.

Universal Studios Florida
Image for Universal Orlando Resort

Universal Orlando Resort

4.5/5(4,155 reviews)

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

Universal Orlando Resort

Things to do

Image for Aquatica Orlando

Aquatica Orlando

$48
Per adult
82% of travellers recommend
Aquatica Orlando
Image for Orlando: Museum of Illusions Admission Ticket

Orlando: Museum of Illusions Admission Ticket

$33
Per adult
84% of travellers recommend
Orlando: Museum of Illusions Admission Ticket
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.