Cheap Flights to Winter Haven from $39
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How Much Does it Cost To Fly To Winter Haven?
The cheapest prices found with in the last 7 days for return flights were $70 and $39 for one-way flights to Winter Haven for the period specified. Prices and availability are subject to change. Additional terms apply
TTN
Mercer
TPA
Tampa Intl.
$76 Roundtrip, found 3 hours ago
$76
Roundtrip
found 3 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| DTW | Tampa | September 8 to September 30 | $70 |
| PHL | Tampa | October 5 to October 15 | $76 |
| TTN | St. Petersburg - Clearwater | August 30 to September 3 | $78 |
| RFD | St. Petersburg - Clearwater | September 14 to September 25 | $100 |
| RFD | St. Petersburg - Clearwater | September 14 to September 25 | $100 |
| SWF | St. Petersburg - Clearwater | September 3 to September 6 | $110 |
| SWF | St. Petersburg - Clearwater | September 3 to September 6 | $110 |
| CLE | Tampa | October 10 to October 16 | $117 |
| PSM | St. Petersburg - Clearwater | August 1 to August 15 | $134 |
| PSM | St. Petersburg - Clearwater | August 1 to August 15 | $134 |
| EWR | Tampa | September 26 to October 3 | $179 |
| MSP | Tampa | September 28 to October 1 | $197 |
| ORD | Tampa | October 19 to November 2 | $204 |
| YYZ | Tampa | September 18 to September 18 | $249 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| RFD | St. Petersburg - Clearwater | July 24 to July 27 | $228 |
| RFD | St. Petersburg - Clearwater | July 24 to July 27 | $228 |
| PSM | St. Petersburg - Clearwater | July 25 to July 29 | $234 |
| PSM | St. Petersburg - Clearwater | July 25 to July 29 | $234 |
| YYZ | Tampa | July 25 to August 11 | $281 |
| CLE | Tampa | July 25 to July 29 | $306 |
| EWR | Tampa | July 25 to July 29 | $310 |
| LGA | Tampa | July 24 to July 28 | $310 |
| MSP | Tampa | July 25 to July 30 | $338 |
| DTW | Tampa | July 25 to July 28 | $357 |
| ORD | Tampa | July 26 to July 31 | $372 |
| SWF | St. Petersburg - Clearwater | July 26 to August 2 | $374 |
| PHL | Tampa | July 26 to August 2 | $375 |
| TTN | St. Petersburg - Clearwater | July 25 to August 8 | $400 |
Winter Haven Flight Information
Traveling to | Winter Haven |
|---|---|
Lowest Price | $70 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Amazing Winter Haven Accommodation Deals
Howard Johnson by Wyndham Winter Haven FL
1300 3rd St Winter Haven FL
$85 nightly
The price is $95 total per night from Jul 20 to Jul 21
$95 total
Jul 20 - Jul 21
Total with taxes and fees
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. ...
7.4/10 Good! (1,000 reviews)
"Horrible and dirty, very dirty."
Reviewed on Jul 17, 2026
Budget Inn Winter Haven
401 6th Street HWY 17N Winter Haven FL
$83 nightly
The price is $93 total per night from Jul 19 to Jul 20
$93 total
Jul 19 - Jul 20
Total with taxes and fees
Stay at this motel in Winter Haven. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions LEGOLAND® Florida and Winter Haven Public Library ...
6.8/10 (293 reviews)
"Ju"
Reviewed on Jul 13, 2026
Rodeway Inn & Suites Winter Haven Chain Of Lakes
1911 Cypress Gardens Blvd Winter Haven FL
$81 nightly
The price is $90 total per night from Jul 21 to Jul 22
$90 total
Jul 21 - Jul 22
Total with taxes and fees
Book a stay at this business-friendly motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LEGOLAND® Florida and Lake ...
5.4/10 (287 reviews)
"No continental breakfast, staff was late upon check in, it’s a 150$ deposit for an already dirty room. Multiple reasons for an uncomfortable stay."
Reviewed on Jul 1, 2026
Save an average of 15% on thousands of hotels when you're signed in
Winter Haven Gardens Inn
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 Dec 18, 2022
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
1300 3rd St Winter Haven FL
$85 nightly
The price is $95 total per night from Jul 20 to Jul 21
$95 total
Jul 20 - Jul 21
Total with taxes and fees
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. ...
7.4/10 Good! (1,000 reviews)
"Horrible and dirty, very dirty."
Reviewed on Jul 17, 2026
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
$96 nightly
The price is $108 total per night from Aug 3 to Aug 4
$108 total
Aug 3 - Aug 4
Total with taxes and fees
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 ...
7/10 Good! (1,000 reviews)
"Has a great view if you are on the lake side. Pool closes at sunset."
Reviewed on Jul 14, 2026
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
1300 3rd St Winter Haven FL
The price is $95 total per night from Jul 20 to Jul 21
$95 total
per night
Jul 20 - Jul 21
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. ...
7.4/10 Good! (1,000 reviews)
"Horrible and dirty, very dirty."
Reviewed on Jul 17, 2026
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
The price is $108 total per night from Aug 3 to Aug 4
$108 total
per night
Aug 3 - Aug 4
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 ...
7/10 Good! (1,000 reviews)
"Has a great view if you are on the lake side. Pool closes at sunset."
Reviewed on Jul 14, 2026
Hampton Inn Winter Haven
202 Cypress Gardens Blvd Winter Haven FL
The price is $128 total per night from Jul 26 to Jul 27
$128 total
per night
Jul 26 - Jul 27
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 ...
9/10 Wonderful! (1,002 reviews)
"Breakfast was good and the staff was very nice and responsive"
Reviewed on Jul 16, 2026
Save an average of 15% on thousands of hotels when you're signed in
Rodeway Inn & Suites Winter Haven Chain Of Lakes
1911 Cypress Gardens Blvd Winter Haven FL
The price is $90 total per night from Jul 21 to Jul 22
$90 total
per night
Jul 21 - Jul 22
Book a stay at this business-friendly motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LEGOLAND® Florida and Lake ...
5.4/10 (287 reviews)
"No continental breakfast, staff was late upon check in, it’s a 150$ deposit for an already dirty room. Multiple reasons for an uncomfortable stay."
Reviewed on Jul 1, 2026
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.
Don't see what you're looking for?
See all available trips from Newark Liberty Intl. Airport to Winter Haven
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See all available trips from Philadelphia to Winter Haven
View all tripsWinter Haven flight + hotel packages - first class flights
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See all available trips from Chicago to Winter Haven
View all tripsNeed a Car For After Your Flight?
Standard
Tampa, USA
$5
$10 total
found 3 days ago
Economy
Tampa, USA
$6
$11 total
found 3 days ago
Compact SUV
Tampa, USA
$7
$13 total
found 3 days ago
Fullsize
Tampa, USA
$7
$13 total
found 3 days ago
Lowest prices found within the past 3 days. Prices and availability subject to change. Additional terms may apply.
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.
More Ways To Wander
Winter Haven Hotels
Find the perfect hotel after your flight
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Winter Haven Car Rentals
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Winter Haven Vacations
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Things to do in Winter Haven
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