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 1 day ago
$76
Roundtrip
found 1 day ago
ORD
O'Hare Intl.
TPA
Tampa Intl.
$111 Roundtrip, found 21 hours ago
$111
Roundtrip
found 21 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| TTN | Tampa | May 18 to May 23 | $76 |
| CLE | Tampa | May 30 to May 31 | $90 |
| DTW | Tampa | June 21 to June 28 | $121 |
| ORD | Tampa | May 17 to May 20 | $139 |
| ORD | Tampa | May 17 to May 20 | $139 |
| LGA | Tampa | June 9 to June 10 | $142 |
| EWR | Tampa | May 13 to May 18 | $159 |
| BOS | Tampa | June 1 to June 10 | $173 |
| MSP | Tampa | May 12 to May 15 | $195 |
| YYZ | Tampa | June 17 to June 26 | $240 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| CLE | Tampa | May 3 to May 8 | $101 |
| TTN | Tampa | May 3 to May 7 | $120 |
| ORD | Tampa | May 1 to May 4 | $176 |
| ORD | Tampa | May 1 to May 4 | $176 |
| MSP | Tampa | May 3 to May 14 | $214 |
| DTW | Tampa | May 2 to May 3 | $232 |
| EWR | Tampa | May 3 to May 6 | $238 |
| EWR | Tampa | May 3 to May 6 | $238 |
| BOS | Tampa | May 1 to May 8 | $247 |
| YYZ | Tampa | May 3 to May 7 | $605 |
Winter Haven Flight Information
Traveling to | Winter Haven |
|---|---|
Lowest Price | $76 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines, Spirit 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
$102 nightly
The price is $114 total per night from Apr 26 to Apr 27
$114 total
Apr 26 - Apr 27
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. ...
7.2/10 Good! (1,015 reviews)
I had a great experience. I highly recommend it for a quick stay.
Reviewed on Apr 20, 2026
Budget Inn Winter Haven
401 6th Street HWY 17N Winter Haven FL
$76 nightly
The price is $86 total per night from May 8 to May 9
$86 total
May 8 - May 9
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 (286 reviews)
Había mucho ruido en la calle, la gente pasaba y no nos dejaban dormir
Reviewed on Apr 23, 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 Apr 26 to Apr 27
$95 total
Apr 26 - Apr 27
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 Peppa ...
5.4/10 (275 reviews)
I had a very mixed experience at Rodeway Inn & Suites Winter Haven Chain of Lakes. The biggest issue was the cleanliness of the room—it did not meet basic expectations. Because of that, we didn’t feel safe or comfortable staying. We ended up only being there for about 3 hours just to rest briefly ...
Reviewed on Apr 22, 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
$102 nightly
The price is $114 total per night from Apr 26 to Apr 27
$114 total
Apr 26 - Apr 27
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. ...
7.2/10 Good! (1,015 reviews)
I had a great experience. I highly recommend it for a quick stay.
Reviewed on Apr 20, 2026
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
$108 nightly
The price is $121 total per night from Apr 26 to Apr 27
$121 total
Apr 26 - Apr 27
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! (1,003 reviews)
Amazing place recomend to all
Reviewed on Apr 23, 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
$102 nightly
The price is $114 total per night from Apr 26 to Apr 27
$114 total
Apr 26 - Apr 27
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. ...
7.2/10 Good! (1,015 reviews)
I had a great experience. I highly recommend it for a quick stay.
Reviewed on Apr 20, 2026
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
$108 nightly
The price is $121 total per night from Apr 26 to Apr 27
$121 total
Apr 26 - Apr 27
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! (1,003 reviews)
Amazing place recomend to all
Reviewed on Apr 23, 2026
Hampton Inn Winter Haven
202 Cypress Gardens Blvd Winter Haven FL
$99 nightly
The price is $111 total per night from May 3 to May 4
$111 total
May 3 - May 4
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! (1,000 reviews)
Excellent
Reviewed on Apr 12, 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 Apr 26 to Apr 27
$95 total
Apr 26 - Apr 27
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 Peppa ...
5.4/10 (275 reviews)
I had a very mixed experience at Rodeway Inn & Suites Winter Haven Chain of Lakes. The biggest issue was the cleanliness of the room—it did not meet basic expectations. Because of that, we didn’t feel safe or comfortable staying. We ended up only being there for about 3 hours just to rest briefly ...
Reviewed on Apr 22, 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.
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View all tripsNeed a Car For After Your Flight?
Compact
Tampa, USA
$7
$13 total
found 1 day ago
Economy
Tampa, USA
$7
$13 total
found 1 day ago
Standard
Tampa, Florida, USA
$7
$19 total
found 1 day ago
Midsize
Tampa, Florida, USA
$8
$15 total
found 14 hours 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
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Winter Haven Vacations
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Things to do in Winter Haven
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