Cheap Flight Deals to Winter Haven FL from CA $138

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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 $112 and CA $138 for one-way flights to Winter Haven for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
BOSTampaJanuary 6 to January 12CA $112
ORDTampaJanuary 14 to January 16CA $147
ORDTampaJanuary 14 to January 16CA $147
JFKTampaJanuary 27 to January 30CA $166
DTWTampaJanuary 14 to January 17CA $169
EWRTampaJanuary 6 to January 13CA $206
PHLTampaMarch 17 to March 21CA $213
YYZTampaJanuary 13 to January 15CA $222
MSPTampaJanuary 20 to January 28CA $240
CLETampaFebruary 11 to February 18CA $259
MSPSt. Petersburg - ClearwaterMarch 13 to March 23CA $427
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
LGATampaDecember 29 to January 9CA $395
MSPTampaDecember 29 to December 31CA $413
BOSTampaDecember 29 to January 3CA $450
ORDTampaDecember 27 to December 29CA $473
ORDTampaDecember 27 to December 29CA $473
EWRTampaDecember 28 to January 4CA $486
DTWTampaDecember 28 to January 4CA $748
YYZTampaDecember 29 to January 1CA $829
*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 $112 and CA $829. Prices vary, but for the best fares, travel in January 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 $112. 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 January 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 $146 per night from Dec. 25 to Dec. 26
CA $146
CA $164 total
includes taxes & fees
25 Dec - 26 Dec
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 (1,003 reviews)
"Nice"

Reviewed on 15 Dec. 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 $129 per night from Dec. 24 to Dec. 25
CA $129
CA $145 total
includes taxes & fees
24 Dec - 25 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 (235 reviews)
"Only thing is the beds were not very comfortable. It was very hard to go to sleep. The beds were hard other than that. It was perfect and they could use some vending machines."

Reviewed on 13 Dec. 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 $171 per night from Jan. 13 to Jan. 14
CA $171
CA $191 total
includes taxes & fees
13 Jan - 14 Jan 2025
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 $146 per night from Dec. 25 to Dec. 26
CA $146
CA $164 total
includes taxes & fees
25 Dec - 26 Dec
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 (1,003 reviews)
"Nice"

Reviewed on 15 Dec. 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 $155 per night from Dec. 24 to Dec. 25
CA $155
CA $174 total
includes taxes & fees
24 Dec - 25 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 (904 reviews)
"Property right on lake. Nice area in back is great for sitting and relaxing. Parking was tight but I was very impressed with the cleanliness of room and property."

Reviewed on 16 Dec. 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 $146 per night from Dec. 25 to Dec. 26
CA $146
CA $164 total
includes taxes & fees
25 Dec - 26 Dec
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 (1,003 reviews)
"Nice"

Reviewed on 15 Dec. 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 $155 per night from Dec. 24 to Dec. 25
CA $155
CA $174 total
includes taxes & fees
24 Dec - 25 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 (904 reviews)
"Property right on lake. Nice area in back is great for sitting and relaxing. Parking was tight but I was very impressed with the cleanliness of room and property."

Reviewed on 16 Dec. 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 $188 per night from Jan. 6 to Jan. 7
CA $188
CA $211 total
includes taxes & fees
6 Jan - 7 Jan 2025
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! (1,003 reviews)
"Nice clean rooms"

Reviewed on 15 Dec. 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 $171 per night from Jan. 13 to Jan. 14
CA $171
CA $191 total
includes taxes & fees
13 Jan - 14 Jan 2025
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.
Highland Down Town Tampa
The Hotel Zamora
Wyndham Grand Clearwater Beach
Don't see what you're looking for?
See all available trips from Toronto to Winter Haven
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Winter Haven flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
Siesta Key Palms Resort
Kompose Boutique Hotel
voco Sarasota, an IHG Hotel
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See all available trips from Toronto to Winter Haven
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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.