Winter Garden Holidays from NZ$3,548
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The Latest Winter Garden Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
NZ$6,842
per person
26 Dec - 2 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)
This place was fantastic to stay at. We had a two bedroom cottage, the facilities were fantastic. All bedrooms ensuite, TVs in every room. Full kitchen and living room. Hot tub. Great pool nearby and sunset walk is five minutes walk away. They had live music in most nights and there is a lot of different food and drink places there.
Reviewed on 15 Oct 2026
Westgate Blue Tree Resort in Lake Buena Vista
NZ$3,823
per person
26 Dec - 2 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Orlando (MCO)
8.6/10 Excellent! (1,000 reviews)
Front desk staff not available between 12 am and 7am. Some days they may be available until 3 am. If you are checking in after hours, please contact hotel to make arrangements. Apartment was clean and well worth the price; well-stocked and better than the popular vacation rentals. Someone is always available and there are no ridiculous fees. Location is excellent- very close to popular theme parks.
Would stay here again!
Reviewed on 17 Oct 2026
Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
NZ$4,328
per person
25 Dec - 1 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Orlando (MCO)
10/10 Exceptional! (11 reviews)
The apt is very clean and new. The location of the property is centric to Disney parks; we Uber everywhere, between 10-18 minutes to the attractions.
There is a shopping center with Marshalls, Keke’s diner; Sports shops, Other chain restaurants like Texas Steak Road or The Olive Garden in the same area.
We did not use the pool or the gym, but there is also a nice, clean outdoor area with grills, tables, pool etc.
The only complain is the address in our reservation was main to the Leasing Office and we spent some time trying to figure out where was our apt, due building was not specified in the confirmation. We call the phone number for the host and he was very friendly and explained us how to get to the right unit.
Reviewed on 7 Oct 2026
Our guide on 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
2 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
1 out of top 10 points of interest in this area
While visiting Killarney, you might make a stop by sights like Oakland Nature Preserve and Johns Lake.
Winter Garden Holiday
Our pick of the best Winter Garden Hotel Deals
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
Fully refundableReserve now, pay when you stay
NZ$493
16 Nov - 17 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
NZ$151
3 Nov - 4 Nov
includes taxes & fees
9.4/10 Exceptional! (5,644 reviews)
"Didn't like they charge $20 dollar parking per day, that I never saw when making the reservation. Never stay there again. With all of the other choices in the area!!!!"
Reviewed on 18 Oct 2026
Home2 Suites by Hilton Orlando at Flamingo Crossings
341 Flagler Ave Winter Garden FL
Fully refundableReserve now, pay when you stay
NZ$194
27 Oct - 28 Oct
includes taxes & fees
9.4/10 Exceptional! (6,162 reviews)
"Clean room, pool and water slide were great kids enjoyed it a lot. Close to Disney so we used uber. Breakfast was good loved the Mickey waffles."
Reviewed on 18 Oct 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.
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.
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.
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.
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.
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.
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.
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
NZ$54
per adult
92% of travellers recommend
Frequently asked questions
How much does a Winter Garden holiday package cost?
Offering great value package deals from NZ$3,548 on Expedia, you'll be thrilled with how little a holiday to Winter Garden costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Winter Garden?
If you're hoping to snag a cheap Winter Garden holiday package, consider visiting in February, September and October. You'll typically find lower prices on hotels and flights during these quieter months — perfect for a budget-friendly break.
How many days is enough for Winter Garden?
When planning your Winter Garden holiday, a handful of days will be enough to tour the top spots. Make sure to stop by Carter Family Bowl — it's one of the most popular attractions in this destination. If you're looking for more activities, consider basing yourself here and heading off on some day tours from Winter Garden.
Is it worth booking a holiday package to Winter Garden?
Well known for its cycling, markets and shopping, a Winter Garden holiday is a hit with all types of travellers. Be sure to check out leading sights like Resurrection Catholic Church and West Orange Trail, and consider renting a car for day trips to explore even more.
How to find the best Winter Garden package deals?
Landing a cheap Winter Garden package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, apply some filters and browse what's available. You can customise your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most affordable Winter Garden package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Winter Garden holiday as a package?
An Expedia holiday package could land you considerable savings when compared to booking accommodation and flights separately. Better still, you can tailor your Winter Garden escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Winter Garden?
If you've got your Winter Garden holiday dates locked in, book as soon as you can to bag some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Winter Garden?
- Choose when to get away: Check your diary and get your bags packed. Your favourite season and the type of activities on offer will also help you decide when to holiday in Winter Garden.
- Calculate your budget: Make sure you have enough money to cover everything from transportation and dining out to activities and airfares. Your accommodation will likely be the largest expense during your trip to Winter Garden.
- Decide your trip length: Think about how much time you want to spend exploring Winter Garden. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Winter Garden holiday package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
