Windsor Hills Holidays from £653

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Your Windsor Hills Holiday

Reserving a tailor-made Windsor Hills holiday package is a good way to get to know this unique neighbourhood. 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 holiday now.

Price found within the past 48 hours. Click for updated prices.
Hilton Orlando Lake Buena Vista - Disney Springs® Area

Hilton Orlando Lake Buena Vista - Disney Springs® Area

£653
per person
8 Dec - 15 Dec
found 1 day ago
Return direct flight included
London (LON) to Orlando (MCO)
8.6/10 Excellent! (1,727 reviews)
The hotel is beautiful and the location is perfect. It's so convenient to be able to walk to the downtown Disney area. Our room was also fantastic with a great view and it was nice and big, giving us plenty of room. Overall, a perfect 10!

Reviewed on 23 Sept 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight
£994
per person
3 Dec - 10 Dec
found 19 hours ago
Return flight included
Dublin (DUB) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

Save 100% on your flight
£727
per person
25 Nov - 2 Dec
found 18 hours ago
Return flight included
London (LON) to Orlando (MCO)
8.4/10 Very good! (7,020 reviews)
The Delaney Hotel

The Delaney Hotel

South Orange
£723
per person
3 Dec - 7 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Orlando (MCO)
9.6/10 Exceptional! (1,202 reviews)
First impressions were great. The suite was huge! The Tavern was awesome, and management resolved concerns promptly. Its a bonus to have access to a fridge and microwave. The coffee makers were nice for making mini coffees. The only suggestion I'd have is to adjust the doors to not slam so loudly! I'd stay here again!

Reviewed on 23 Sept 2026

Vista Cay by Orlando Resort Rentals on Universal Boulevard

Vista Cay by Orlando Resort Rentals on Universal Boulevard

£750
per person
8 Dec - 15 Dec
found 1 day ago
Return direct flight included
London (LON) to Orlando (MCO)
9.4/10 Exceptional! (1,008 reviews)
The resort in itself was okay. My family loved how close everywhere was to the resort and the pools were nice. The 2 bedroom apartment that we occupied was overall okay. I believe that it could have been more clean because we did discover that the main bedroom was a bit dusty. I noticed that certain furniture and the walls of the room had some noticeable dust particles, which unfortunately, resulted in my family, including my baby, developing a slight cold and being congested our entire stay. Also, the dryer machine was not heating properly which was a major inconvenience for me and my family as our stay was for 7 days. When we called the customer service number, we were advised that someone will check it out for us the next day but nobody ever came. I was quite disappointed that the issue wasn’t resolved. This resulted in us having to hang out our clothes and towels to dry on the balcony. Besides the dust in the apartment and the dryer machine, our stay was okay. I’m not certain if I would book here again, but if we somehow do, I hope it would be a better experience.

Reviewed on 22 Sept 2026

Things to do near Windsor Hills

Windsor Hills offers a delightful blend of family-friendly activities and entertainment options, perfect for an outdoor holiday. Visitors can enjoy nearby theme parks, exciting vacation attractions, and vibrant shopping areas. For golf enthusiasts, there are attractive golf villas, while water parks provide refreshing fun for the whole family. This destination is ideal for those seeking a memorable escape filled with adventure and leisure.

Shopping

For a delightful shopping experience near Windsor Hills, visit Disney Springs™, just 9.7km away, offering a vibrant family atmosphere. Old Town, 8.0km away, combines entertainment and shopping. Don't miss the 192 Flea Market, 14.5km away, perfect for unique gifts and souvenirs in a bustling setting.

Recreation

ESPN Wide World of Sports Complex, located 4.8km from Windsor Hills, offers a vibrant atmosphere for sports enthusiasts. Mystic Dunes Golf Club, just 1.1km away, provides a stunning outdoor setting for golf lovers. For relaxation, Northeast Regional Park, 6.4km from Windsor Hills, is perfect for wellness and tranquility.

Adventure

Disney's Typhoon Lagoon Water Park, located 8.0km from Windsor Hills, offers thrilling water rides and family-friendly attractions. Similarly, Disney's Blizzard Beach Water Park, merely 3.2km away, features a snowy theme with exciting slides. For more aquatic fun, Aquatica, situated 17.7km away, provides adventurous experiences for all ages.

Nightlife

For a lively evening in Windsor Hills, venture to Indigo's Family Fun Center, a charming drinking pub located 37.0km away. Here, you can enjoy a delightful atmosphere filled with entertainment and romance, perfect for unwinding after a day of exploring Florida's attractions.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Windsor Hills

Windsor Hills is perfect for families seeking an entertaining outdoor holiday, with attractions such as theme parks, lakes, and golf courses nearby. Visitors can enjoy the Windsor Hills Water Park, explore the magic of Disney World, or relax at Windsor Palms. This destination offers a memorable experience tailored for those craving adventure and fun in the sun.

  • Walt Disney World® Resort: Experience the magic at this iconic theme park, located 11.3km from Windsor Hills. With a plethora of attractions, enchanting characters, and immersive themed lands, it's a haven for families seeking adventure and entertainment, making unforgettable memories.
  • Orange County Convention Center: Situated 16.1km away, this arts centre is a cultural gem. Hosting various exhibitions and events, it showcases vibrant local art and provides a platform for creativity, making it a fantastic spot for art enthusiasts and cultural explorers.
  • Universal CityWalk: Located 20.9km from Windsor Hills, this lively tourist precinct offers outdoor dining, shopping, and entertainment. With its vibrant atmosphere, it's perfect for families looking to unwind and enjoy a variety of attractions in a bustling environment.

Best time to go to Windsor Hills

The best time to visit Windsor Hills is dependant on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with moderate rain. January is its coolest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January60.6°F (15.9°C)Light RainMostly SunnySlightly HighAverage
February64.4°F (18.0°C)Light RainMostly SunnyAverageAverage
March67.6°F (19.8°C)Light RainMostly SunnySlightly HighSlightly High
April72.7°F (22.6°C)Light RainMostly SunnySlightly HighSlightly High
May77.2°F (25.1°C)Light RainMostly SunnyAverageAverage
June81.1°F (27.3°C)Light RainMostly SunnyAverageAverage
July82.4°F (28.0°C)Moderate RainMostly SunnyAverageAverage
August82.6°F (28.1°C)Moderate RainMostly SunnyAverageSlightly Low
September80.4°F (26.9°C)Moderate RainMostly SunnyAverageSlightly Low
October75.2°F (24.0°C)Light RainMostly SunnySlightly LowAverage
November68.5°F (20.3°C)Light RainMostly SunnySlightly LowSlightly Low
December64.4°F (18.0°C)No RainMostly SunnySlightly LowSlightly High

Tips to save on your trip to Windsor Hills

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Windsor Hills.
  • Consider traveling to Windsor Hills during the low season (August to September and November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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
A traditional Japanese torii gate with a dragon sculpture in front, overlooking a calm lake with a distant view of a spherical building.

Bay Lake

3 out of top 10 points of interest in this area

Exciting theme parks plentiful wildlife and top sights from Epcot® to Walt Disney World® Resort – discover Bay Lake, a destination also famous for its entertainment.

Find hotels in Bay Lake
A theme park with a large rock formation, Old-Town sign, and various food and restaurant signs.

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
A city skyline with modern buildings, a lake with swans, and a fountain.

Florida Center

2 out of top 10 points of interest in this area

If you're spending some time in Florida Center, Universal Orlando Resort and Universal Studios Florida are top sights worth seeing.

Find hotels in Florida Center
A large Ferris wheel with blue lighting, surrounded by a parking lot and buildings.

Champions Gate

Ample dining options and top golf courses are well-reviewed features of Champions Gate. Make a stop by top sights like ChampionsGate Golf Club while you're exploring the area.

Find hotels in Champions Gate
A golf course with sand bunkers, a water hazard, and a clubhouse in the background.

Reunion

The top golf courses and fun-filled water parks are top of the list for many visitors to Reunion. A stop by Reunion Resort Golf Course or Jack Nicklaus Course might round out your trip.

Find hotels in Reunion

Top hotels in Windsor Hills

Newly Totally Renovated-Video Game Room-Private Pool

Newly Totally Renovated-Video Game Room-Private Pool

Kissimmee FL
9.6/10 Exceptional! (105 reviews)
"Enjoyed our stay! Kids enjoyed the pool. Home was close to Disney. Owners very responsive to any questions we had. Home was clean and comfortable for our family of 5."

Reviewed on 9 Aug 2026

Get rates
Newly Totally Renovated-Video Game Room-Private Pool
🌴Beautiful home in Windsor Hills Resort -Disney 2.5 miles 🌴

🌴Beautiful home in Windsor Hills Resort -Disney 2.5 miles 🌴

Kissimmee FL
9.8/10 Exceptional! (202 reviews)
"Rental was perfect!!! Have nothing negative to say!!"

Reviewed on 8 Sept 2026

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🌴Beautiful home in Windsor Hills Resort -Disney 2.5 miles 🌴
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 FL
Get rates
6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
See all 1,787 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.
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Frequently asked questions

Why should I book my Windsor Hills holiday with Expedia?
With exceptional-value flights, accommodation and car hire choices all in the same place, Expedia makes booking your Windsor Hills holiday a piece of cake. What's more, we can help you bundle your bookings into a package holiday so you can get even more savings. Choose from wonderful stays, add flights and/or a car hire (and maybe even some exciting activities!) and land incredible prices. Need to change plans? Expedia offers a flexible cancellation policy for many reservations. To discover more, check out our Customer Service Portal link.
What are the top hotels for my holiday in Windsor Hills?
Get your holiday off to an excellent start by booking a room at Luxury 6 bedroom 4 bath villa with south facing pool 10 minutes from Disney. It's one of the most sought-after properties for those wanting to be near Windsor Hills. Another welcoming option close by is 2mi to Disney, Windsor Hills Villa w/ themed bdrms.
How do I get a cheap holiday to Windsor Hills?
Booking a Windsor Hills holiday with Expedia is one of the best ways to save. We have access to more than 400 airlines and 321,000 properties spread across the globe. With such an awesome range to pick from, you'll have no hassles putting together your next dream getaway. Learn more about how you can save money on your next holiday when you book a flight and hotel together with Expedia.
What should I do on my Windsor Hills holiday?
Make sure your next holiday in Windsor Hills is one to remember by taking in its leading attractions. Orange Lake Golf, Northeast Regional Park, Surfari Water Park and Lake Davenport are just some of the things to put on your itinerary while you're in the city.
Do I need a visa for my Windsor Hills holiday?
Official government websites are the best source of information on visa requirements, application procedures and any necessary documentation. Your nationality and the purpose of your visit, whether it be for work or pleasure, will determine if you need a visa for Windsor Hills. Also make sure your passport is up to date and has a minimum of six months validity remaining after the date of your intended return. Do all your travel planning well in advance to avoid any nasty last-minute surprises.
What should I wear on my Windsor Hills holiday?
Do some research into the sorts of things people in Windsor Hills wear, and maybe even look up style blogs for some fashion tips. Try to create a versatile wardrobe with pieces that work for your destination and show off your unique style.
What does an Expedia Windsor Hills holiday include?
It all depends on what sort of trip you're contemplating. Windsor Hills holiday deals can include hotels, flights and car hires. You can mix and match to create the package that fits your needs. You can also add on activities and experiences after you've booked to pick up even bigger discounts. Expedia has a wide selection of properties in Windsor Hills, allowing you the freedom to tailor your escape. Private holiday homes and villas are two of the most in-demand stays for our guests here.
Does Expedia offer Book Now, Pay Later Windsor Hills holidays?
Expedia has partnered with online lender Klarna to make booking your next break easier on your wallet. Paying in instalments means you can spread the costs of your dream holiday, leaving you with more cash to splash while you're travelling. Klarna has several payment plans to pick from, so you're sure to find something that suits your budget. Browse these flexible payment options:
  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's convenient payment plans. If paying across multiple instalments works for you, pick this option during the checkout process.
  • No-deposit holidays: Clicking the "book now" button is easier with this payment plan. With no upfront fee for your escape, you can Book Now, Pay Later and start packing your suitcase.
Can I choose my airline with a Windsor Hills Expedia holiday?
You sure can. We offer more than 400 partner airlines around the world, so choose the carrier that's a good fit for your needs.

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

£20
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Aquatica Orlando

Aquatica Orlando

£43
per traveller
84% of travellers recommend
Aquatica Orlando
"Drawn to Life" presented by Cirque du Soleil and Disney

Drawn to Life presented by Cirque du Soleil and Disney

£62
per adult
94% of travellers recommend
Drawn to Life presented by Cirque du Soleil and Disney
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. Flight-inclusive packages are ATOL protected.