Winter Garden Holidays from £746
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Your Winter Garden Holiday
Come and discover this interesting city for yourself with a Winter Garden holiday package. Consider basing yourself in the neighbourhood of Lake Buena Vista North, which is great for shopping and dining, and your time here will be nothing short of unforgettable. Like to start exploring your surroundings? West Orange Trail, Winter Garden Art Association and Winter Garden Heritage Museum are among the leading places to visit during a trip to Winter Garden. Whoever you're heading away with and whatever your budget, your ultimate Winter Garden holiday is just clicks away with Expedia.
Top Winter Garden Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
£2,322
per person
28 Dec - 4 Jan
found 1 day ago
Return direct flight included
London (LHR) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)
We stayed in one of the cottages and it was just perfect. The fully equipped kitchen downstairs with a master suite was perfect for my parents. I appreciated having the laundry upstairs with the other bedrooms.
The staff at the main building were so helpful with our packages and printing documents for us.
Unfortunately we had a very busy week and could not enjoy the wonderful amenities of the resort.
Overall, a great selection and would start again!
Reviewed on 25 Sept 2026
Where to stay in Winter Garden
Find the best Winter Garden areas and neighborhoods for the activities you enjoy most. Learn more about Winter Garden
Oakland
Oakland might not have many top sights, but Garden Theatre and West Orange Trail are two attractions nearby that you can check out.
Downtown Winter Garden
3 out of top 10 points of interest in this area
If you're spending some time in Downtown Winter Garden, Garden Theatre and Winter Garden Heritage Museum are top sights worth seeing.
Killarney
While visiting Killarney, you might make a stop by sights like Oakland Nature Preserve and Johns Lake.
Winter Garden Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Orlando Intl. Airport (MCO) |
Population | 40,400 |
Max Temp Winter | 21ºC |
Max Temp Summer | 32ºC |
Top Sights | Walt Disney World® Resort, Universal Orlando Resort and Magic Kingdom® Park |
Top hotels in Winter Garden
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
Fully refundableReserve now, pay when you stay
£186
4 Nov - 5 Nov
includes taxes & fees
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
631 FLAGLER AVE Winter Garden FL
Fully refundableReserve now, pay when you stay
£76
26 Oct - 27 Oct
includes taxes & fees
9.4/10 Exceptional! (5,582 reviews)
"This hotel was perfect for our weekend stay. Rooms were clean and staff is friendly. The hotel was around a lot places to grab food and having a target so close by was a plus. Even loved being about to go downstairs and get frozen yogurt whenever we wanted! Will be staying here again!"
Reviewed on 5 Oct 2026
Home2 Suites by Hilton Orlando at Flamingo Crossings
341 Flagler Ave Winter Garden FL
Fully refundableReserve now, pay when you stay
£83
28 Oct - 29 Oct
includes taxes & fees
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.
Stay near popular Winter Garden attractions
Flamingo Crossings Town Center
8.6/10 (131 reviews)
This convenient retail hub at Disney World's western gateway offers diverse shopping and dining options. Explore Target, Walgreens, and restaurants in a pedestrian-friendly environment perfect for a theme park break.
Disney's Palm Golf Course
8.4/10 (457 reviews)
This championship course winds through Florida woodlands with shimmering lakes and tropical sands. Enjoy complimentary range balls before navigating the Arnold Palmer-redesigned fairways and strategic water hazards.
Disney's Magnolia Golf Course
8.4/10 (552 reviews)
This championship course stretches through scenic magnolia trees with challenging water hazards on 11 holes. Enjoy Walt Disney-themed hole names and inspiring quotes while navigating the recently reimagined greens.
Orange County National Golf Club
8.4/10 (647 reviews)
Orange County National offers two championship courses with rolling fairways and elevation changes. Test your skills on the meticulously maintained greens or practice at the massive 42-acre circular driving range.
Surfari Water Park
9.0/10 (2,086 reviews)
Ride the waves on a dual FlowRider surf simulator or float along the 695-foot lazy river at this tropical oasis. Reserve a private cabana for a luxurious day of family fun at The Grove Resort.
West Orange Trail
8.4/10 (337 reviews)
This 22-mile paved trail winds through historic Winter Garden and natural Florida landscapes. Perfect for cyclists and walkers with charming city centre cafés and peaceful picnic spots along this scenic former railway corridor.
Garden Theatre
8.4/10 (219 reviews)
Enjoy a show at Garden Theatre, a theatre with a story to tell in Winter Garden. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
Disney's Oak Trail Golf Course
8.4/10 (377 reviews)
This 9-hole walking course doubles as a certified Audubon Wildlife Sanctuary within Walt Disney World. Enjoy a leisurely round on rolling greens while spotting diverse Florida wildlife along the scenic fairways.
What to do in Winter Garden
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
£23
per adult
92% of travellers recommend
Old Town Kissimmee: Ferris Wheel, Mortem Manor, and Meal
£11
per adult
Frequently asked questions
Why should I book my Winter Garden holiday with Expedia?
Choose Expedia to organise your next big break simply and all in the same place. Our top tip for bagging the best deal on a Winter Garden retreat? Bundle your accommodation, airfares and/or car hire into a package holiday. Then add some fun tours and activities. Most bookings also include flexible cancellation policies, so there's no need to worry if you have to change your travel plans. Round-the-clock help with changing and cancelling your trip is on-hand via our Customer Service Portal link.
When is the best time of year to holiday in Winter Garden?
Winter Garden is very popular in January, February and March. If you're not into big crowds and prefer a more relaxed pace, book your getaway for April, May and December. Organise your trip to Winter Garden based on what type of adventure you're looking for. January is the coolest month, when daytime temperatures average 15ºC. In August, the warmest period, you'll experience temperatures of around 28ºC during the day.
What are the top hotels for my holiday in Winter Garden?
The Grove Resort & Water Park Orlando in the Vista del Lago neighbourhood is a terrific choice for a Winter Garden holiday. Check in here and you'll be perfectly placed to get out and discover all that this city has to offer.
How do I get a cheap holiday to Winter Garden?
Our Winter Garden holidays mean plenty of savings for the savvy wanderer. For the best deals, simply combine your flights, hotels and extras (such as activities). But great bargains are just the beginning of your next epic adventure. Book with Expedia and you'll have more than 400 air carriers and 321,000 hotel options across the globe to select from. No matter your style, there's a holiday here just for you. Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Winter Garden holiday?
Ensure your holiday in Winter Garden is one to remember by checking out its major attractions. Universal Studios Florida, The Wizarding World of Harry Potter™, Central Florida Fairgrounds and Arnold Palmers Bay Hill Golf Club are just a few of the things to put on your itinerary while you're in the area.
What is the best area to stay in when on holiday in Winter Garden?
If you'll be visiting Orange County National Golf Club, maximise your time sightseeing and find a place to stay close by. It's one of the top attractions in Winter Garden.
Do I need a visa for my Winter Garden holiday?
Official government websites will have all the information you need on visa requirements, application procedures and any supporting documentation. Your nationality and reason for visiting, whether it be for tourism or work, will determine if you need a visa for Winter Garden. Also make sure your passport is up to date and has at least six months validity remaining beyond your planned date of return. Finalise all your travel planning well in advance to avoid any nasty last-minute surprises.
What should I wear on my Winter Garden holiday?
First, consider the sorts of activities you have planned during your trip to Winter Garden and select versatile pieces that you can easily mix and match. For fashion inspiration or even information on dress codes, look up a few style blogs or relevant social media accounts. Be sure to look at the local weather forecast so you can pack accordingly. The warmest time of year in Winter Garden is August, with average daily temperatures of 28ºC. If you're travelling during the coolest month of January, the mercury hovers around 15ºC during the day.
What does an Expedia Winter Garden holiday include?
Hotels, flights and a cool car for all your fun road trip adventures. Simply pick and choose your favourite bundle and gain access to great discounts. Once you've made your booking, add on some experiences and tours and watch your savings grow. When it comes to crafting your Winter Garden break, you're the boss! Explore a large selection of property types and choose one that matches the size of your group. The most popular holiday rentals here are condos and private holiday homes. With Expedia, you can easily tailor-make your Winter Garden escape just the way you like.
Does Expedia offer Book Now, Pay Later Winter Garden holidays?
Expedia has joined forces with online lender Klarna to make booking your next break easier on your wallet. Paying by instalment means you can spread the costs of your next dream escape, 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 one that fits into your budget. Check out these flexible payment options:
- Pay monthly holidays: Klarna offers the ability to pay in multiple transactions that suit all types of budgets, so you can jet away on that well-deserved holiday sooner.
- No-deposit holidays: Pressing the "book now" button is much easier with this plan. With no upfront fee for your escape, you can Book Now, Pay Later and get on your way.
Can I choose my airline with a Winter Garden Expedia holiday?
Yes, and with more than 400 airlines to choose from all over the world, you have plenty of choice. Search the available options and see which airline fits your budget and needs.
Explore a world of travel with Expedia
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- Apopka Holidays
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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.
