Windsor Hills Vacations from $172
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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.
Palazzo Lakeside Hotel
Price was $489, price is now $172 per person
$172
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (5,145 reviews)
I never leave reviews, but this place deserves one. It was so clean and employees were so nice. Breakfast was good and a breeze, and lasted all the way til 930 which most places do not do. I’ll definitely be staying here again next time.
Reviewed on Dec 11, 2025
Residence Inn by Marriott Daytona Beach Oceanfront
Price was $1,423, price is now $542 per person
$542
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
The outside of the building could use some tlc but inside was clean and updated. Staff was attentive, polite, & helpful. Breakfast was surprisingly better than I anticipated with hot options outside of the traditional continental options. Furniture around pool was pressure washed every morning and plentiful. There are no seating options for the beach however we would definitely stay here again.
Reviewed on Nov 30, 2025
The Shores Resort & Spa
Price was $957, price is now $386 per person
$386
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9/10 Wonderful! (1,681 reviews)
The room, hallways everywhere was clean and smelled wonderful.
From the minute, I arrived until I left on the second day all employees were quick to assist very pleasant very professional. This was a very relaxing stay I will definitely be back.
Reviewed on Dec 12, 2025
Westgate Cocoa Beach Resort
Price was $2,184, price is now $993 per person
$993
per person
Mar 9 - Mar 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (500 reviews)
No Beach view but beach is an10m walk so not too bad. Beach chairs falling apart. The pools and tiki bar were awesome. The two room suite was okay and for the most part pretty clean. But there were some dead bugs which is not what I expected for the price point.
Reviewed on Nov 6, 2025
Parkway International Resort
Price was $1,059, price is now $494 per person
$494
per person
Jan 31 - Feb 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.6/10 Exceptional! (2,052 reviews)
Events each night are a nice touch. Perfect for us with our toddlers.
Reviewed on Dec 11, 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
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.
Windsor Hills Hotel Deals
Windsor Hills Condo w/all things Mickey. Pool/Waterpark and minutes from Disney!
Kissimmee FL
9.6/10 Exceptional! (23 reviews)
Great location, amazing bedroom for the kids, and all around great place
Reviewed on Nov 5, 2025
Spacious 3 Bedroom TownHome..3 minutes from Disney World!
Kissimmee FL
10/10 Exceptional! (101 reviews)
The condo is exactly what the pictures show! It’s immaculate and every detail has been thought of which is nice. The proximity to Magic Kingdom was 15 min max. So easy!The communication from owner was perfect and easy. We will definitely recommend this place and when back in Orlando would rent this ...
Reviewed on Nov 24, 2025
Disney World 2 Miles! Family condo
Kissimmee FL
$240 nightly
The price is $268 total per night from Dec 14 to Dec 15
$268 total
Dec 14 - Dec 15
Total with taxes and fees
8.8/10 Excellent! (34 reviews)
Great location and great pool for the little ones
Reviewed on Nov 10, 2025
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
90% of travellers recommend
Universal Orlando Resort Express Passes
$202
per traveler
86% of travellers recommend
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- Walt Disney World® Resort
- Disney's Hollywood Studios®
- Orlando Vacations
- Mystic Dunes Golf Club
- Disney's Animal Kingdom® Theme Park
- Bonanza Golf & Gifts
- Mighty Jungle Golf
- Island H2O Live!
- Disney's Maingate West Vacations
- Disney's Blizzard Beach Water Park
- Four Corners Vacations
- Visit Disney's Maingate West
- Central Florida Vacations
- Disney's Winter Summerland Miniature Golf Course
- ESPN Wide World of Sports
- Car rental Orlando Airport (MCO)
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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.