Windsor Hills Vacations from $257
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Your Windsor Hills Vacation
Take all the hassle out of planning your next escape with a Windsor Hills vacation package. Take in the sights and sounds of this enticing neighborhood and experience all it has to offer. Eager to sightsee during your trip to Windsor Hills? Be sure to check out nearby attractions like Mystic Dunes Golf Club, Orange Lake Golf and Jack Nicklaus Course. Stop dreaming and start doing. When it's time to book your dream vacation to Windsor Hills, Expedia will help you get there.
The Latest Windsor Hills Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort
Save 100% on your flight
Price was $501, price is now $257 per person
$257
per person
May 15 - May 19
found 21 hours ago
Roundtrip flight included
New York (LGA) to Orlando (MCO)
8/10 Very Good! (1,820 reviews)
Absolutely a great place to stay. Will be going back for sure.
Reviewed on Mar 13, 2026
Westgate River Ranch Resort & Rodeo
Price was $898, price is now $402 per person
$402
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
8.2/10 Very Good! (427 reviews)
My granddaughter loved the covered wagon cabin and the golf cart. We were not told that Thursdays the animals rest so we couldn’t do the horseback riding and petting zoo. We were not told the rodeo is only on Saturday nights so plan accordingly.
Reviewed on Mar 11, 2026
Westgate Lakes Resort & Spa Universal Studios Area
Save 100% on your flight
Price was $912, price is now $415 per person
$415
per person
May 3 - May 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.4/10 Very Good! (5,960 reviews)
Friendly. Provided great recommendations
Reviewed on Mar 14, 2026
Westgate Palace Hotel / Universal / I-Drive
International Drive District
Price was $1,232, price is now $563 per person
$563
per person
May 3 - May 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (1,234 reviews)
The hotel is nice and convenient to universal studios. The rooms are clean but having to call housekeeping everyday to get your trash picked up or fresh towels was a hassle. One time no one answered and we had to walk down to the front desk to get someone. With kids this was a pain and the elevators were always out of commission everyday. Our last day we only had one working one that was delayed with everyone needing it.
Reviewed on Mar 1, 2026
Westgate Town Center Resort
Save 100% on your flight
Price was $775, price is now $375 per person
$375
per person
May 3 - May 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8/10 Very Good! (1,510 reviews)
I was there for three nights. They never came to clean my room .
Reviewed on Mar 12, 2026
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
Adventure activities, iconic attractions, shopping and world-class dining destinations make this famous street one of Orlando’s most popular tourist attractions.
Windsor Hills Hotel Deals
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 Feb 19, 2026
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 Feb 14, 2026
Windsor Hills Private Luxury Pool House, Sleeps 13
Kissimmee FL
9/10 Wonderful! (163 reviews)
Great amenities, lots of room, clean!
Reviewed on Feb 4, 2026
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.
Discover the most popular places to visit in Windsor Hills
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.
Universal Studios Florida
4.5/5(9,273 reviews)
Thrill rides based on your favorite movies create this internationally acclaimed theme park.
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.
Things to do
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
$27
per adult
92% of travellers recommend
Universal Orlando Resort Express Passes
$192
per traveler
82% of travellers recommend
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- Walt Disney World® Resort
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- Orlando Vacations
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- Island H2O Live!
- Disney's Maingate West Vacations
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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.