Cheap Flight Deals to Winter Garden FL from CA $130

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

How to find cheap flights to Winter Garden?

The cheapest prices found with in the last 7 days for return flights were CA $78 and CA $130 for one-way flights to Winter Garden for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
BOSOrlandoApril 9 to April 16CA $78
PHLOrlandoMay 2 to May 6CA $118
EWROrlandoMay 10 to May 14CA $140
EWROrlandoMay 10 to May 14CA $140
DTWOrlandoMay 31 to June 4CA $146
ORDOrlandoMay 5 to May 9CA $146
JFKOrlandoMay 10 to May 14CA $185
MSPOrlandoJune 29 to July 8CA $199
SJUOrlandoApril 4 to April 7CA $232
LAXOrlandoApril 26 to May 3CA $253
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
BOSOrlandoApril 6 to April 15CA $98
EWROrlandoApril 4 to April 8CA $141
EWROrlandoApril 4 to April 8CA $141
PHLOrlandoApril 4 to April 8CA $170
DTWOrlandoApril 5 to April 9CA $188
JFKOrlandoApril 6 to April 15CA $228
SJUOrlandoApril 4 to April 7CA $232
MSPOrlandoApril 5 to April 12CA $233
ORDOrlandoApril 4 to April 11CA $256
LAXOrlandoApril 4 to April 8CA $321
*Prices include taxes and fees

Your guide to flights to Winter Garden, FL

Flair Airlines fly to Winter Garden, so use Travelocity to search, find, and compare some truly tempting deals from the 2 airlines—that way you can be sure you’ve found the best deal for you. A flight to Winter Garden FL currently costs between CA $78 and CA $321. Prices vary, but for the best fares, travel in April when prices are at their lowest.  

Top tips for finding cheap flights to Winter Garden  

The cheapest flight for a round trip to Winter Garden is currently CA $78. When you search for flights to Winter Garden, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Winter Garden for nearby days.  The cheapest month to travel to Winter Garden is April from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to Winter Garden 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to Winter Garden with Travelocity 

We have top deals on plane tickets even for last minute flights to Winter Garden, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Winter Garden for less. 

Find The Perfect Hotel For After Your Flight

Amazing Place to Stay After Flight to Winter Garden

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

4 out of 5
17777 Bali Blvd, Winter Garden, FL
The price is CA $154 per night from Apr. 8 to Apr. 9
CA $154
CA $214 total
includes taxes & fees
8 Apr - 9 Apr
Stay at this 4-star family-friendly hotel in Winter Garden. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff ...
8.8/10 Excellent! (3,697 reviews)
"Great facility, great location for a Disney trip."

Reviewed on 27 Mar. 2025

Hilton Vacation Club Aqua Sol Orlando West
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

3.5 out of 5
13279 Hartzog Road, Winter Garden, FL
The price is CA $142 per night from Apr. 20 to Apr. 21
CA $142
CA $159 total
includes taxes & fees
20 Apr - 21 Apr
Stay at this 3.5-star business-friendly hotel in Winter Garden. Enjoy free breakfast, free WiFi, and a free theme park shuttle. Our guests praise the breakfast ...
9/10 Wonderful! (2,046 reviews)
"El hotel esta en muy buena ubicación,"

Reviewed on 27 Mar. 2025

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
The Palisades Resort Orlando

The Palisades Resort Orlando

2 out of 5
14200 Avalon Road, Winter Garden, FL
Book a stay at this family-friendly hotel in Winter Garden. Enjoy free parking, a fitness center, and a business center. Popular attractions Disney's Animal ...
7.4/10 Good! (998 reviews)
Worst ever
"Check your notes I've called and I'm very upset thinking about taking legal action against you and them"

Reviewed on 13 Sep. 2017

The Palisades Resort Orlando
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.

Luxury Hotels in Winter Garden

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

4 out of 5
17777 Bali Blvd, Winter Garden, FL
The price is CA $154 per night from Apr. 8 to Apr. 9
CA $154
CA $214 total
includes taxes & fees
8 Apr - 9 Apr
Stay at this 4-star family-friendly hotel in Winter Garden. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff ...
8.8/10 Excellent! (3,697 reviews)
"Great facility, great location for a Disney trip."

Reviewed on 27 Mar. 2025

Hilton Vacation Club Aqua Sol Orlando West
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 $248 per night from Apr. 28 to Apr. 29
CA $248
CA $351 total
includes taxes & fees
28 Apr - 29 Apr
Stay at this 4-star family-friendly resort in Winter Garden. Enjoy free WiFi, 5 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful ...
8/10 Very Good! (7,238 reviews)
"Great staff. Denisse was awesome and so sweet! Pool area not big enough for amount of people booked. Need to get in pool like an hour before it opens to get seats."

Reviewed on 26 Mar. 2025

The Grove Resort & Water Park Orlando
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

3.5 out of 5
13279 Hartzog Road, Winter Garden, FL
The price is CA $142 per night from Apr. 20 to Apr. 21
CA $142
CA $159 total
includes taxes & fees
20 Apr - 21 Apr
Stay at this 3.5-star business-friendly hotel in Winter Garden. Enjoy free breakfast, free WiFi, and a free theme park shuttle. Our guests praise the breakfast ...
9/10 Wonderful! (2,046 reviews)
"El hotel esta en muy buena ubicación,"

Reviewed on 27 Mar. 2025

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
Save an average of 15% on thousands of hotels when you're signed in
Edgewater Hotel

Edgewater Hotel

2.5 out of 5
99 W Plant St, Winter Garden, FL
The price is CA $192 per night from Apr. 6 to Apr. 7
CA $192
CA $217 total
includes taxes & fees
6 Apr - 7 Apr
Stay at this B&B in Winter Garden. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (278 reviews)
"This was a great surprise! Amazing hotel/bed & breakfast, charming town! So much fun! The staff whe t above and beyond!"

Reviewed on 7 Mar. 2025

Edgewater Hotel
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.

Family Friendly Hotels in Winter Garden

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

4 out of 5
17777 Bali Blvd, Winter Garden, FL
The price is CA $154 per night from Apr. 8 to Apr. 9
CA $154
CA $214 total
includes taxes & fees
8 Apr - 9 Apr
Stay at this 4-star family-friendly hotel in Winter Garden. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff ...
8.8/10 Excellent! (3,697 reviews)
"Great facility, great location for a Disney trip."

Reviewed on 27 Mar. 2025

Hilton Vacation Club Aqua Sol Orlando West
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

3.5 out of 5
13279 Hartzog Road, Winter Garden, FL
The price is CA $142 per night from Apr. 20 to Apr. 21
CA $142
CA $159 total
includes taxes & fees
20 Apr - 21 Apr
Stay at this 3.5-star business-friendly hotel in Winter Garden. Enjoy free breakfast, free WiFi, and a free theme park shuttle. Our guests praise the breakfast ...
9/10 Wonderful! (2,046 reviews)
"El hotel esta en muy buena ubicación,"

Reviewed on 27 Mar. 2025

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
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 $248 per night from Apr. 28 to Apr. 29
CA $248
CA $351 total
includes taxes & fees
28 Apr - 29 Apr
Stay at this 4-star family-friendly resort in Winter Garden. Enjoy free WiFi, 5 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful ...
8/10 Very Good! (7,238 reviews)
"Great staff. Denisse was awesome and so sweet! Pool area not big enough for amount of people booked. Need to get in pool like an hour before it opens to get seats."

Reviewed on 26 Mar. 2025

The Grove Resort & Water Park Orlando
Save an average of 15% on thousands of hotels when you're signed in
The Palisades Resort Orlando

The Palisades Resort Orlando

2 out of 5
14200 Avalon Road, Winter Garden, FL
Book a stay at this family-friendly hotel in Winter Garden. Enjoy free parking, a fitness center, and a business center. Popular attractions Disney's Animal ...
7.4/10 Good! (998 reviews)
Worst ever
"Check your notes I've called and I'm very upset thinking about taking legal action against you and them"

Reviewed on 13 Sep. 2017

The Palisades Resort Orlando
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.

Best Winter Garden Flight and Hotel Packages

Winter Garden flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Boardwalk Inn and Suites
Westgate Cocoa Beach Resort
The Resort on Cocoa Beach
Don't see what you're looking for?
See all available trips from Calgary to Winter Garden
View all trips

Winter Garden flight + hotel packages - premium economy flights

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort
ette hotel
Westgate Vacation Villas Resort
Don't see what you're looking for?
See all available trips from Calgary to Winter Garden
View all trips

Winter Garden flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
Boardwalk Inn and Suites
Meliá Orlando Celebration
Don't see what you're looking for?
See all available trips from Toronto to Winter Garden
View all trips

Need a car after flight to Winter Garden?

Plane Tickets To Winter Garden

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Winter Garden. Browse through our inventory to explore a wide range of cheap flights to Winter Garden to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Winter Garden as you anxiously await to exit the plane and explore what Winter Garden has to offer. Considering all the amazing local food and culture in Winter Garden, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Winter Garden to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Winter Garden without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Winter Garden with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Winter Garden today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.