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.
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Davis
per person
Oct 4 - Oct 11
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.4/10 Very Good! (1,341 reviews)
Need black out blinds for light

Reviewed on Aug. 3, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
per person
Oct 25 - Oct 31
found 10 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8.6/10 Excellent! (1,006 reviews)
We found a cockroach in the room. Some linen was dirty.

Reviewed on Aug. 3, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
per person
Sep 27 - Oct 1
found 10 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Orlando (MCO)
8.2/10 Very Good! (5,097 reviews)
Property was great only reason it wasn’t a 5 star review is they have early closings of waterpark and bars. The place could really be better about providing times for all amenities without having to go to them. That being said the staff is friendly room was very nice and family friendly things to do. We will definitely be back!

Reviewed on Aug. 3, 2025

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.8/10 Excellent! (479 reviews)
Decent place. Spacious 2/2 with full kitchen and living room. A bit dated but clean. No room service and food stops at 830. Drinks are overpriced, overall a decent experience. Walking distance to the beach. Great location! Great for kids!

Reviewed on Jul. 29, 2025

Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Reunion
per person
Oct 11 - Oct 18
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.8/10 Excellent! (1,331 reviews)
Great place if you are a big family or group. Tons of room. Full kitchen. Loved the shuttle service to the amenities.

Reviewed on Aug. 3, 2025

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
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Vista del Lago

While Vista del Lago isn't home to many top sights, Orange Lake Golf and Island H2O Live! are some notable places to visit nearby.

Find hotels in Vista del Lago

Ready to book your vacation to Winter Garden?

 

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Winter Garden Hotel Deals

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 $151 per night from Aug 13 to Aug 14
CA $151
CA $170 total
Aug 13 - Aug 14
includes taxes & fees
9.2/10 Wonderful! (4,369 reviews)
"Accodating staff, qiet, clean, great pool"

Reviewed on Aug. 1, 2025

Home2 Suites by Hilton Orlando at Flamingo Crossings
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from Aug 5 to Aug 6
CA $205
CA $293 total
Aug 5 - Aug 6
includes taxes & fees
7.8/10 Good! (8,229 reviews)
"We had to make 2 calls upon checking in. We were missing a shower curtain in the bathroom, no hand soap in bathrooms and not enough towels in the rooms upon arrival."

Reviewed on Aug. 2, 2025

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

2.5 out of 5
631 FLAGLER AVE, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Aug 14 to Aug 15
CA $128
CA $144 total
Aug 14 - Aug 15
includes taxes & fees
9.4/10 Exceptional! (3,564 reviews)
"I love stayong at the"

Reviewed on Aug. 3, 2025

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
See all 53,876 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Winter Garden

Flamingo Crossings Town Center

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.

Flamingo Crossings Town Center

Surfari Water Park

Enjoy a fun-filled day at Surfari Water Park as part of your trip to Four Corners. Make time for the shops and golf courses in this family-friendly area.

Surfari Water Park

Central Florida Railroad Museum

You can study the exhibits at Central Florida Railroad Museum, a museum with a story of its own, during your travels to Winter Garden. Amble around this family-friendly area's lakeside, or seek out the adventure tours.

Central Florida Railroad Museum

What to do in Winter Garden

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

CA $91
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Aquatica Orlando

Aquatica Orlando

CA $66
per traveller
82% of travellers recommend
Aquatica Orlando
Titanic : The Artifact Exhibition Ticket in Orlando

Titanic : The Artifact Exhibition Ticket in Orlando

CA $47
per adult
90% of travellers recommend
Titanic : The Artifact Exhibition Ticket in Orlando
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 $459 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.