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 $82 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.
$82 Roundtrip, found 6 days ago
$82
Roundtrip
found 6 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| TTN | Tampa | August 30 to September 6 | $88 |
| CLE | Tampa | August 29 to August 29 | $93 |
| SWF | Tampa | August 26 to September 2 | $145 |
| EWR | Tampa | August 25 to September 1 | $177 |
| BOS | Tampa | August 20 to August 25 | $193 |
| DTW | Tampa | September 9 to September 16 | $193 |
| MSP | Tampa | July 25 to July 31 | $197 |
| RFD | Tampa | July 21 to July 28 | $213 |
| ORD | Tampa | August 25 to September 2 | $221 |
| YYZ | Tampa | August 12 to August 16 | $278 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| SWF | Tampa | June 13 to June 17 | $241 |
| PHL | Tampa | June 13 to June 17 | $242 |
| CLE | Tampa | June 14 to June 16 | $268 |
| MDW | Tampa | June 13 to June 20 | $294 |
| EWR | Tampa | June 13 to June 16 | $302 |
| BOS | Tampa | June 14 to June 19 | $349 |
| MSP | Tampa | June 12 to June 16 | $360 |
| ORD | Tampa | June 13 to June 20 | $407 |
| DTW | Tampa | June 13 to June 20 | $408 |
| YYZ | Tampa | June 13 to June 22 | $620 |
Winter Haven Flight Information
Traveling to | Winter Haven |
|---|---|
Lowest Price | $82 |
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 Jun 11 to Jun 12
$95 total
Jun 11 - Jun 12
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! (1,014 reviews)
"No me gusto el aire acondicionado fatal. Toda la noche tumbando y un ruido terrible dejaba de enfriar.Mas no me limpiaron la habitación al menos recojer la basura. Los matress estan de cambiar."
Reviewed on Jun 8, 2026
Budget Inn Winter Haven
401 6th Street HWY 17N Winter Haven FL
$83 nightly
The price is $93 total per night from Jun 10 to Jun 11
$93 total
Jun 10 - Jun 11
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
$81 nightly
The price is $90 total per night from Jun 29 to Jun 30
$90 total
Jun 29 - Jun 30
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 ...
5.2/10 (282 reviews)
"Everything was good other than the photo shows they provide breakfast. The staff were very helpful, it would be nicer if the vending machines carried diet drinks for us diabetic people also if they provided some type of complementary waters that would be nice other than that it was okay for the ..."
Reviewed on Jun 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 Jun 11 to Jun 12
$95 total
Jun 11 - Jun 12
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! (1,014 reviews)
"No me gusto el aire acondicionado fatal. Toda la noche tumbando y un ruido terrible dejaba de enfriar.Mas no me limpiaron la habitación al menos recojer la basura. Los matress estan de cambiar."
Reviewed on Jun 8, 2026
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
$98 nightly
The price is $110 total per night from Jun 10 to Jun 11
$110 total
Jun 10 - Jun 11
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)
"The room was ok beds was terrible back breaking the shower didn't work until I had them install a new shower head the front door would close but now solid could be picked open with a butter knife toilet was clogged when we got there I had to plunge it to get the toilet paper cardboard out my tablet ..."
Reviewed on Jun 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 Jun 11 to Jun 12
$95 total
Jun 11 - Jun 12
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! (1,014 reviews)
"No me gusto el aire acondicionado fatal. Toda la noche tumbando y un ruido terrible dejaba de enfriar.Mas no me limpiaron la habitación al menos recojer la basura. Los matress estan de cambiar."
Reviewed on Jun 8, 2026
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
$98 nightly
The price is $110 total per night from Jun 10 to Jun 11
$110 total
Jun 10 - Jun 11
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)
"The room was ok beds was terrible back breaking the shower didn't work until I had them install a new shower head the front door would close but now solid could be picked open with a butter knife toilet was clogged when we got there I had to plunge it to get the toilet paper cardboard out my tablet ..."
Reviewed on Jun 3, 2026
Hampton Inn Winter Haven
202 Cypress Gardens Blvd Winter Haven FL
$115 nightly
The price is $128 total per night from Jun 21 to Jun 22
$128 total
Jun 21 - Jun 22
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! (1,009 reviews)
"Nice hot powerful shower."
Reviewed on Jun 8, 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
$81 nightly
The price is $90 total per night from Jun 29 to Jun 30
$90 total
Jun 29 - Jun 30
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 ...
5.2/10 (282 reviews)
"Everything was good other than the photo shows they provide breakfast. The staff were very helpful, it would be nicer if the vending machines carried diet drinks for us diabetic people also if they provided some type of complementary waters that would be nice other than that it was okay for the ..."
Reviewed on Jun 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.
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See all available trips from Cleveland to Winter Haven
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Price found within the past 48 hours. Click for updated prices.
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See all available trips from Newark Liberty Intl. Airport to Winter Haven
View all tripsWinter Haven flight + hotel packages - first class 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?
Standard
Tampa, USA
$5
$10 total
found 20 hours ago
Economy
Tampa, USA
$6
$11 total
found 20 hours ago
Compact SUV
Tampa, Florida, USA
$7
$14 total
found 20 hours ago
Fullsize
Tampa, Florida, USA
$7
$15 total
found 20 hours ago
Lowest prices found within the past 20 hours. 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
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