Winter Garden Holidays

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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
A calm lake with lily pads and reeds in the foreground, surrounded by trees and a cloudy sky.

Oakland

Oakland might not have many top sights, but Winter Garden Art Association and West Orange Trail are two attractions nearby that you can check out.

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A tree-lined sidewalk with parked cars and a clear sky.

Downtown Winter Garden

3 out of top 10 points of interest in this area

If you're spending some time in Downtown Winter Garden, Winter Garden Art Association and West Orange Trail are top sights worth seeing.

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A wooden pier extending into a calm body of water, surrounded by lush greenery and a distant forest.

Killarney

While visiting Killarney, you might make a stop by sights like Oakland Nature Preserve and Johns Lake.

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Top hotels in Winter Garden

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue Winter Garden FL
Fully refundableReserve now, pay when you stay
S$314
24 Aug - 25 Aug
includes taxes & fees
8/10 Very good! (10,758 reviews)
"Having enough space for the whole family and room to feel like a home away from Home."

Reviewed on 12 Aug, 2026

The Grove Resort & Water Park Orlando
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

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
S$102
26 Aug - 27 Aug
includes taxes & fees
9.4/10 Exceptional! (5,384 reviews)
"Staff was great very clean place breakfast was a little on the down side eggs didn’t taste that great and no bacon just a spicy sausage or veggie sausage"

Reviewed on 12 Aug, 2026

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

341 Flagler Ave Winter Garden FL
Fully refundableReserve now, pay when you stay
S$114
26 Aug - 27 Aug
includes taxes & fees
Home2 Suites by Hilton Orlando at Flamingo Crossings
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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.
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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.
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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.
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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.
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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.
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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.
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Winter Garden Art Association

8.4/10 (276 reviews)
Housed in a historic firehouse, SOBO Art Gallery showcases diverse works from local Florida artists. Visitors can immerse themselves in monthly exhibits or join workshops for hands-on creative experiences.
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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.
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What to do in Winter Garden

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

S$45
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

S$35
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets

S$199
per adult
78% of travellers recommend
Universal Orlando Resort Theme Park Tickets
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Frequently asked questions

How much does a Winter Garden holiday package cost?
Offering great value package deals 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?
  1. 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.
  2. 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.
  3. 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.
  4. 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.