Cheap Flight Deals to Winter Haven FL from CA $171

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How to find cheap flights to Winter Haven?

The cheapest prices found with in the last 7 days for return flights were CA $109 and CA $171 for one-way flights to Winter Haven for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
BOSTampaDecember 12 to December 18CA $109
DTWTampaFebruary 2 to February 16CA $137
ORDTampaDecember 8 to December 11CA $164
ORDTampaDecember 8 to December 11CA $164
JFKTampaDecember 3 to December 10CA $193
EWRTampaDecember 17 to December 18CA $201
CLETampaFebruary 19 to February 25CA $204
MSPTampaDecember 13 to December 19CA $208
MSPSt. Petersburg - ClearwaterJanuary 26 to January 26CA $236
YYZTampaDecember 7 to December 13CA $288
PHLTampaDecember 3 to December 11CA $291
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
ORDTampaNovember 29 to December 5CA $303
ORDTampaNovember 29 to December 5CA $303
YYZTampaNovember 29 to December 10CA $309
LGATampaNovember 29 to December 7CA $322
DTWTampaNovember 30 to December 12CA $358
MSPTampaNovember 30 to December 7CA $363
EWRTampaNovember 29 to December 7CA $464
BOSTampaNovember 30 to December 4CA $490
CLETampaNovember 29 to December 2CA $494
PHLTampaNovember 29 to December 11CA $518
*Prices include taxes and fees

Your guide to flights to Winter Haven, FL

Porter Airlines fly to Winter Haven, 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 Haven FL currently costs between CA $109 and CA $518. Prices vary, but for the best fares, travel in December when prices are at their lowest.  

Top tips for finding cheap flights to Winter Haven  

The cheapest flight for a round trip to Winter Haven is currently CA $109. When you search for flights to Winter Haven, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Winter Haven for nearby days.  The cheapest month to travel to Winter Haven is December 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 Haven 

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 Haven with Travelocity 

We have top deals on plane tickets even for last minute flights to Winter Haven, 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 Haven for less. 

Find The Perfect Hotel For After Your Flight

Amazing Place to Stay After Flight to Winter Haven

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St Sw, Cypress Gardens & US 17 South, Winter Haven, FL
The price is CA $143 per night from Nov. 26 to Nov. 27
CA $143
CA $160 total
includes taxes & fees
26 Nov - 27 Nov
Stay at this motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.8/10 (1,002 reviews)
"Property was ok, Should have been more staff at the counter, had to pay a $50 room essential fee, which we got back after the room was checked."

Reviewed on 12 Nov. 2024

Howard Johnson by Wyndham Winter Haven FL
Budget Inn Winter Haven

Budget Inn Winter Haven

2 out of 5
401 6th Street HWY 17N, Winter Haven, FL
The price is CA $118 per night from Dec. 7 to Dec. 8
CA $118
CA $133 total
includes taxes & fees
7 Dec - 8 Dec
Stay at this motel in Winter Haven. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions LEGOLAND® Florida and Rotary Park are located ...
6.6/10 (233 reviews)
Clean hotel
"The stay was great the checkout time is a no.. 10:30 wasn’t good most places are 11am"

Reviewed on 30 Jun. 2024

Budget Inn Winter Haven
Rodeway Inn & Suites Winter Haven Chain Of Lakes

Rodeway Inn & Suites Winter Haven Chain Of Lakes

2 out of 5
1911 Cypress Gardens Blvd, Winter Haven, FL
The price is CA $203 per night from Dec. 24 to Dec. 25
CA $203
CA $227 total
includes taxes & fees
24 Dec - 25 Dec
Book a stay at this business-friendly motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LEGOLAND® Florida and Baytree ...
5.4/10 (234 reviews)
"I like the staff. They call me when I didn’t check in and I find out that I made a mistake on the day on my reservation. I didn’t like that it show in the link that they have free breakfast and that did not include."

Reviewed on 10 Sep. 2024

Rodeway Inn & Suites Winter Haven Chain Of Lakes
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Winter Haven Gardens Inn

Winter Haven Gardens Inn

2.5 out of 5
1150 3rd Street SW, Winter Haven, FL
Stay at this hotel in Winter Haven. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions LEGOLAND® Florida and Indigo's Family Fun Center ...
5.8/10 (1,000 reviews)
Booked a hotel that was permanently closed
"Didn't stay. Got here and sign on door saying permanent closed. Had to find somewhere else to stay at last minute. Good thing other family members had extra room and allowed us to stay with them."

Reviewed on 18 Dec. 2022

Winter Haven Gardens Inn
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 Haven

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St Sw, Cypress Gardens & US 17 South, Winter Haven, FL
The price is CA $143 per night from Nov. 26 to Nov. 27
CA $143
CA $160 total
includes taxes & fees
26 Nov - 27 Nov
Stay at this motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.8/10 (1,002 reviews)
"Property was ok, Should have been more staff at the counter, had to pay a $50 room essential fee, which we got back after the room was checked."

Reviewed on 12 Nov. 2024

Howard Johnson by Wyndham Winter Haven FL
Lake Roy Beach Inn

Lake Roy Beach Inn

2 out of 5
1823 Cypress Gardens Blvd, Winter Haven, FL
The price is CA $122 per night from Dec. 14 to Dec. 15
CA $122
CA $137 total
includes taxes & fees
14 Dec - 15 Dec
Book a stay at this beach hotel in Winter Haven. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
6.8/10 (902 reviews)
"Beautiful view"

Reviewed on 17 Nov. 2024

Lake Roy Beach Inn
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 Haven

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St Sw, Cypress Gardens & US 17 South, Winter Haven, FL
The price is CA $143 per night from Nov. 26 to Nov. 27
CA $143
CA $160 total
includes taxes & fees
26 Nov - 27 Nov
Stay at this motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.8/10 (1,002 reviews)
"Property was ok, Should have been more staff at the counter, had to pay a $50 room essential fee, which we got back after the room was checked."

Reviewed on 12 Nov. 2024

Howard Johnson by Wyndham Winter Haven FL
Lake Roy Beach Inn

Lake Roy Beach Inn

2 out of 5
1823 Cypress Gardens Blvd, Winter Haven, FL
The price is CA $122 per night from Dec. 14 to Dec. 15
CA $122
CA $137 total
includes taxes & fees
14 Dec - 15 Dec
Book a stay at this beach hotel in Winter Haven. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
6.8/10 (902 reviews)
"Beautiful view"

Reviewed on 17 Nov. 2024

Lake Roy Beach Inn
Hampton Inn Winter Haven

Hampton Inn Winter Haven

2.5 out of 5
202 Cypress Gardens Blvd, Winter Haven, FL
The price is CA $153 per night from Nov. 24 to Nov. 25
CA $153
CA $172 total
includes taxes & fees
24 Nov - 25 Nov
Book a stay at this business-friendly hotel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,000 reviews)
"Great"

Reviewed on 30 Oct. 2024

Hampton Inn Winter Haven
Save an average of 15% on thousands of hotels when you're signed in
Rodeway Inn & Suites Winter Haven Chain Of Lakes

Rodeway Inn & Suites Winter Haven Chain Of Lakes

2 out of 5
1911 Cypress Gardens Blvd, Winter Haven, FL
The price is CA $203 per night from Dec. 24 to Dec. 25
CA $203
CA $227 total
includes taxes & fees
24 Dec - 25 Dec
Book a stay at this business-friendly motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LEGOLAND® Florida and Baytree ...
5.4/10 (234 reviews)
"I like the staff. They call me when I didn’t check in and I find out that I made a mistake on the day on my reservation. I didn’t like that it show in the link that they have free breakfast and that did not include."

Reviewed on 10 Sep. 2024

Rodeway Inn & Suites Winter Haven Chain Of Lakes
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 Haven Flight and Hotel Packages

Winter Haven flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
St Pete Beach Suites
The Hotel Zamora
Hilton St. Petersburg Carillon Park
Don't see what you're looking for?
See all available trips from Toronto to Winter Haven
View all trips

Winter Haven flight + hotel packages - business class flights

Price found within the past 48 hours. Click for updated prices.
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
The Gemma by Brightwild
Element Tampa Midtown
Don't see what you're looking for?
See all available trips from Toronto to Winter Haven
View all trips

Winter Haven flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
Element Tampa Midtown
The Avalon Club
Home2 Suites by Hilton Tampa Downtown Channel District
Don't see what you're looking for?
See all available trips from Toronto to Winter Haven
View all trips

Need a car after flight to Winter Haven?

Frequently asked questions

Which airlines fly to Winter Haven?
When it comes to airlines that fly to Winter Haven,you’re not short on choice.There are 20companiesthat service this major city.Book your favorite seat on one ofthese well-known carriers:

  • Southwest Airlines
  • Delta Air Lines
  • American Airlines

What airport is best to fly into Winter Haven?
Get a feel for the layout of Winter Haven before locking in your airfares. This will assist to avoid problems when you arrive, as the city has a number of airports. The most popular are:

  • MCO – 64 kilometers from downtown
  • Tampa Airport – 80 kilometers from downtown
  • ORL – 72 kilometers from downtown

Where to stay in Winter Haven
Few things are as satisfying as jumping into bed after a busy day of seeing the sights. With 184 accommodations in Winter Haven, you can take your pick of the cushiest of them.Finding accommodations can sometimes be a tedious task. Make the process as easy as possible and check out a few of our recommended options, the Fall/winter Special Rates Mid - Century Mod W and the Budget Inn Winter Haven.
Places to visit in Winter Haven
Want some vacation inspiration? Don’t leave this lively metropolis until you’ve visited Chain of Lakes Park, and Legoland Florida.0 Like some more options? 0 But that’s not all. 0
How to get through airport security fast when traveling to Winter Haven
Make your trip to Winter Haven that little bit easier by following these handy security tips:

  • Airport security personnel will ask to see your passport and boarding pass upon arrival. Tuck them away in a convenient place, so they’re all ready for inspection.
  • Belts, wallets and power banks are to be placed in a bin for X-raying. If you walk into the body scanner with any of these items, you’ll be instructed to turn back and remove them.
  • Make sure your electronic devices and laptop are easy to reach. These items need to be put through the X-ray machine in separate bins.
  • Lip balm, toothpaste and other toiletry items in gel, liquid or cream form need to be stored in containers smaller than 3.4 ounces (100 milliliters). They must also fit in a 1-quart (1-liter) clear zip-lock plastic bag.
  • Steel-cap boots and other heavy shoes tend to be X-rayed by security personnel. Think about wearing lightweight sneakers instead.
  • Put any pocketknives or other sharp and pointy items in your checked luggage. Airport security won’t permit such things in carry-on baggage.

Flights To Winter Haven

Situated within striking range of both Orlando and Tampa, Winter Haven is a popular spot within Central Florida, as the combo of amusement parks, picturesque natural areas, excellent water skiing spots, and laid-back atmosphere make it a place where you can have fun without feeling in a rush. Hence, it's a true Florida town. If you plan on getting here via air, you're in luck too, as you can choose to land at either Orlando International Airport (MCO) or Tampa International Airport (TPA).

Transportation from TPA and MCO

If you've found some great deals for Winter Haven flights landing at Tampa International Airport, know you'll be roughly 57 miles from the city when you arrive. Thus, your best option is to rent a car in the baggage claim area, though you could catch a taxi outside the baggage claim level, or book a shuttle van. If you've discovered some good flights to Winter Haven that land at Orlando International Airport, know you'll be roughly 48 miles from the city when you arrive. Hence, your most convenient option is to also get a rental vehicle, which can be arranged on the ground transportation level of any terminal at MCO. It is possible to take a public bus from MCO to Winter Haven, but there are numerous transfers, and it's very time consuming. After all, you'll want to drop your bags off at your choice of Winter Haven hotels and go explore as quick as possible.

Experience Winter Haven

Enjoy the rides at Legoland Florida, and fish at Lake Hamilton while in Winter Haven. If you want to find discount plane tickets and hotel rooms for Winter Haven, look no further than Travelocity. We offer a price match guarantee, which means that if you find cheaper airfare to Winter Haven or lower cost packages to Winter Haven elsewhere, we'll match that price and refund the difference.

*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.