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 $76 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 6 days ago
$76
Roundtrip
found 6 days ago
CVG
Cincinnati - Northern Kentucky Intl.
PIE
St. Petersburg-Clearwater Intl.
$81 Roundtrip, found 4 hours ago
$81
Roundtrip
found 4 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| TTN | St. Petersburg - Clearwater | October 1 to October 15 | $78 |
| TTN | St. Petersburg - Clearwater | October 1 to October 15 | $78 |
| RFD | St. Petersburg - Clearwater | September 14 to September 25 | $108 |
| RFD | St. Petersburg - Clearwater | September 14 to September 25 | $108 |
| PSM | St. Petersburg - Clearwater | August 8 to August 15 | $109 |
| PSM | St. Petersburg - Clearwater | August 8 to August 15 | $109 |
| DTW | Tampa | September 16 to October 7 | $109 |
| SWF | St. Petersburg - Clearwater | September 3 to September 6 | $117 |
| SWF | St. Petersburg - Clearwater | September 3 to September 6 | $117 |
| CLE | Tampa | September 11 to September 14 | $124 |
| EWR | Tampa | September 9 to September 15 | $163 |
| MSP | Tampa | September 12 to September 19 | $188 |
| ORD | Tampa | August 25 to September 2 | $209 |
| YYZ | Tampa | September 21 to September 25 | $249 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| PSM | St. Petersburg - Clearwater | July 18 to July 22 | $154 |
| PSM | St. Petersburg - Clearwater | July 18 to July 22 | $154 |
| TTN | St. Petersburg - Clearwater | July 18 to July 29 | $154 |
| TTN | St. Petersburg - Clearwater | July 18 to July 29 | $154 |
| CLE | Tampa | July 18 to July 25 | $192 |
| EWR | Tampa | July 18 to July 28 | $265 |
| EWR | Tampa | July 18 to July 28 | $265 |
| RFD | St. Petersburg - Clearwater | July 17 to July 27 | $280 |
| RFD | St. Petersburg - Clearwater | July 17 to July 27 | $280 |
| DTW | Tampa | July 19 to August 19 | $282 |
| YYZ | Tampa | July 17 to July 19 | $291 |
| SWF | St. Petersburg - Clearwater | July 19 to July 21 | $309 |
| ORD | Tampa | July 18 to July 28 | $337 |
| MSP | Tampa | July 17 to July 21 | $337 |
Winter Haven Flight Information
Traveling to | Winter Haven |
|---|---|
Lowest Price | $76 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines, Allegiant Air |
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 19 to Jul 20
$95 total
Jul 19 - Jul 20
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! (1,009 reviews)
"The first night I arrived there was a rain storm and it knocked the internet out which also affected the cable. Once it was restored I chilled a little then want to shower and no hot water. It was 1:00 in the morning there was nothing really anyone can do at that time. Front desk did offer to move ..."
Reviewed on Jul 11, 2026
Budget Inn Winter Haven
401 6th Street HWY 17N Winter Haven FL
$83 nightly
The price is $93 total per night from Jul 12 to Jul 13
$93 total
Jul 12 - Jul 13
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 (292 reviews)
"I enjoyed my stay, would stay again"
Reviewed on Jun 1, 2026
Rodeway Inn & Suites Winter Haven Chain Of Lakes
1911 Cypress Gardens Blvd Winter Haven FL
$85 nightly
The price is $95 total per night from Jul 12 to Jul 13
$95 total
Jul 12 - Jul 13
Total with taxes and fees
Book a stay at this business-friendly motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LEGOLAND® Florida and Lake ...
5.4/10 (287 reviews)
"No continental breakfast, staff was late upon check in, it’s a 150$ 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 19 to Jul 20
$95 total
Jul 19 - Jul 20
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! (1,009 reviews)
"The first night I arrived there was a rain storm and it knocked the internet out which also affected the cable. Once it was restored I chilled a little then want to shower and no hot water. It was 1:00 in the morning there was nothing really anyone can do at that time. Front desk did offer to move ..."
Reviewed on Jul 11, 2026
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
$98 nightly
The price is $110 total per night from Jul 12 to Jul 13
$110 total
Jul 12 - Jul 13
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! (1,001 reviews)
"You expect quaint. You get unsafe, unsanitary and rudeness. You realize from the check-in through a tiny gated slot that this is not going well. You climb the rickety stairs up and follow the uneven hallway down to the room and use your old fashioned door key to enter. Inside the room is extremely ..."
Reviewed on Jul 3, 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
$85 nightly
The price is $95 total per night from Jul 19 to Jul 20
$95 total
Jul 19 - Jul 20
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! (1,009 reviews)
"The first night I arrived there was a rain storm and it knocked the internet out which also affected the cable. Once it was restored I chilled a little then want to shower and no hot water. It was 1:00 in the morning there was nothing really anyone can do at that time. Front desk did offer to move ..."
Reviewed on Jul 11, 2026
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
$98 nightly
The price is $110 total per night from Jul 12 to Jul 13
$110 total
Jul 12 - Jul 13
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! (1,001 reviews)
"You expect quaint. You get unsafe, unsanitary and rudeness. You realize from the check-in through a tiny gated slot that this is not going well. You climb the rickety stairs up and follow the uneven hallway down to the room and use your old fashioned door key to enter. Inside the room is extremely ..."
Reviewed on Jul 3, 2026
Hampton Inn Winter Haven
202 Cypress Gardens Blvd Winter Haven FL
$87 nightly
The price is $98 total per night from Jul 23 to Jul 24
$98 total
Jul 23 - Jul 24
Total with taxes and fees
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)
"I’ve stayed at this property multiple times in the past and never had a problem until this time. First off there were ants everywhere in the room. You can tell they don’t clean. The smell in the room was horrendous. My poor daughter even found an ant on her pillow. To top it off my toilet was clogged ..."
Reviewed on Jul 7, 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
$85 nightly
The price is $95 total per night from Jul 12 to Jul 13
$95 total
Jul 12 - Jul 13
Total with taxes and fees
Book a stay at this business-friendly motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LEGOLAND® Florida and Lake ...
5.4/10 (287 reviews)
"No continental breakfast, staff was late upon check in, it’s a 150$ deposit for an already dirty room. Multiple reasons for an uncomfortable stay."
Reviewed on Jul 1, 2026
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
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View all tripsNeed a Car For After Your Flight?
Standard
Tampa, USA
$5
$10 total
found 1 day ago
Economy
Tampa, USA
$6
$11 total
found 1 day ago
Compact SUV
Tampa, USA
$7
$13 total
found 1 day ago
Fullsize
Tampa, USA
$7
$13 total
found 1 day ago
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
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Winter Haven Vacation Rentals
Great Deals on alternative accommodations
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Affordable cars to get you around town
Winter Haven Vacations
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