Winter Garden Vacation Packages

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Your Winter Garden Vacation

Come and discover this interesting city for yourself with a Winter Garden vacation package. Consider basing yourself in the neighborhood 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 vacation is just clicks away with Expedia.

Top Winter Garden Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
International Drive District
Price was CA $1,350, price is now CA $857 per person
CA $857
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
7.8/10 Good! (524 reviews)
This is a good hotel and is in close proximity to major activities. However, the breakfast fell short. My family is allergic to eggs especially my daughter who has a very bad reaction to eggs. The only protein offered was cold hard boiled eggs. I asked the staff if they would be putting out sausage or bacon or something else and she told me only eggs will be offered. There was bread, small bagels, corn flakes. So if you a breakfast person and have egg allergies bear this in mind.

Reviewed on Jul 6, 2026

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was CA $3,634, price is now CA $1,586 per person
CA $1,586
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Orlando (MCO)
8.2/10 Very good! (1,977 reviews)
All the amenities were very dated and old, things were kept up but needed to be largely redone as a whole. The mini golf and swan boats were boring the pools included were very very average at best. The water park admission was not included in my reservation but when we paid to go we were underwhelmed. There were not enough supplies in the room, trash bags and toilet paper, and I wasn’t under the impression this was an Airbnb type of situation where we would have to purchase that.

Reviewed on Jul 6, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was CA $2,981, price is now CA $1,795 per person
CA $1,795
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
9.2/10 Wonderful! (1,006 reviews)
Excellent location

Reviewed on Jul 2, 2026

Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Price was CA $1,534, price is now CA $943 per person
CA $943
per person
Sep 12 - Sep 19
found 18 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Orlando (MCO)
8.6/10 Excellent! (1,003 reviews)
This was our 2nd time staying here. Rooms are amazing. Highly recommended.

Reviewed on Jul 5, 2026

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was CA $1,473, price is now CA $927 per person
CA $927
per person
Aug 15 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Orlando (MCO)
9/10 Wonderful! (1,275 reviews)
Super clean and easy access

Reviewed on Jul 6, 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
A calm lake with lily pads and reeds in the foreground, surrounded by trees and a cloudy sky.

Oakland

When in Oakland, you can plan a visit to Bella Collina Golf Club and Winter Garden Art Association, some noteworthy sights in the nearby area.

Find hotels in Oakland

Ready to book your vacation to Winter Garden?

 

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Winter Garden Hotel Deals

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
The price is CA $268 per night from Aug 4 to Aug 5
CA $268
CA $380 total
Aug 4 - Aug 5
includes taxes & fees
8/10 Very good! (10,354 reviews)
"Beautiful room, family friendly, water park was amazing. Definitely will book another stay."

Reviewed on Jul 6, 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

3 out of 5
631 FLAGLER AVE Winter Garden FL
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from Aug 2 to Aug 3
CA $124
CA $139 total
Aug 2 - Aug 3
includes taxes & fees
9.4/10 Exceptional! (5,136 reviews)
"I had a wonderful stay at the Fairfield by Marriott in Florida. The hotel was clean, comfortable, and well maintained. The staff was friendly and welcoming, making check-in and check-out quick and easy. The complimentary breakfast had a good variety of options, and the overall experience exceeded ..."

Reviewed on Jul 6, 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

3 out of 5
341 Flagler Ave Winter Garden FL
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Jul 19 to Jul 20
CA $139
CA $156 total
Jul 19 - Jul 20
includes taxes & fees
9.4/10 Exceptional! (5,719 reviews)
"I wasnt aware that they will be a parking fee of $20 a day had to keep asking for towels and for garbage to be trown out also they have a team member with a nasty attitude"

Reviewed on Jul 6, 2026

Home2 Suites by Hilton Orlando at Flamingo Crossings
See all 53,653 properties in Winter Garden
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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Stay near popular Winter Garden attractions

Flamingo Crossings Town Center

8.6/10 (131 reviews)
You can do some window-shopping at Flamingo Crossings Town Center during your visit to Winter Garden. Discover the top-notch restaurants and entertainment choices in this family-friendly area.
See properties

What to do in Winter Garden

Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets (US & Canada)

CA $239
per adult
86% of travellers recommend
Universal Orlando Resort Theme Park Tickets (US & Canada)
Aquatica Orlando

Aquatica Orlando

CA $82
per traveller
86% of travellers recommend
Aquatica Orlando
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

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

CA $43
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
See all activities in Winter Garden

Frequently asked questions

How much does a Winter Garden vacation package cost?
You can grab a vacation package to this destination from CA $857 on Expedia. But how much your vacation to Winter Garden costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Winter Garden?
You're likely to find lower prices and greater availability in February, September and October. Browse our cheap Winter Garden vacation packages and you could get some great off-season deals.
How many days is enough for Winter Garden?
You can visit all the major attractions in Winter Garden in a few days, including the popular Winter Garden Art Association. If you're after a longer Winter Garden vacation, check out what kind of activities and excursions are available in the area.
Is it worth booking a vacation package to Winter Garden?
Winter Garden has everything you need for a fantastic break — cycling, markets and shopping are just the start. Whether you want to visit sights such as Resurrection Catholic Church and West Orange Trail, or venture off the beaten track, you'll have plenty to experience on your Winter Garden vacation.
How to find the best Winter Garden package deals?
Finding a cheap Winter Garden package deal is a breeze with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, add a few filters and see what's available. You can personalize your search by "Area," "Amenities," "Property type" 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 often lower.
Is it cheaper to book a Winter Garden vacation as a package?
You can enjoy significant savings on your Winter Garden break by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Winter Garden?
Score incredible bargains by booking your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Winter Garden escape.
How to plan a trip to Winter Garden?

  1. Choose when to travel: Check your diary and get your bags packed. Your preferred time of year and the available activities will also help you decide when to visit Winter Garden.
  2. Set your budget: Consider costs like flights, meals and transportation when working out how much to save for your trip to Winter Garden. Then, select a hotel that suits your budget, whether that's a low-cost option or a high-end getaway.
  3. Decide your trip length: Consider how much time you'd like to spend exploring Winter Garden. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Winter Garden vacation 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.