Cheap Flights to Winter Haven from $38
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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 $38 for one-way flights to Winter Haven for the period specified. Prices and availability are subject to change. Additional terms apply
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$76 Roundtrip, just found
$76
Roundtrip
just found
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| PHL | Tampa | June 6 to June 10 | $76 |
| CLE | Tampa | July 14 to July 22 | $98 |
| SWF | Tampa | May 30 to June 3 | $133 |
| DTW | Tampa | June 9 to June 23 | $172 |
| ORD | Tampa | May 26 to June 23 | $173 |
| ORD | Tampa | May 26 to June 23 | $173 |
| MSP | Tampa | May 17 to May 24 | $188 |
| EWR | Tampa | May 24 to June 2 | $193 |
| BOS | Tampa | May 23 to May 29 | $202 |
| YYZ | Tampa | July 27 to July 27 | $270 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| CLE | Tampa | May 10 to May 17 | $131 |
| MDW | Tampa | May 10 to May 11 | $241 |
| DTW | Tampa | May 9 to May 16 | $262 |
| PHL | Tampa | May 9 to May 11 | $262 |
| MSP | Tampa | May 10 to May 12 | $265 |
| SWF | Tampa | May 9 to May 16 | $268 |
| ORD | Tampa | May 10 to May 17 | $298 |
| BOS | Tampa | May 9 to May 15 | $470 |
| EWR | Tampa | May 9 to May 14 | $521 |
| YYZ | Tampa | May 10 to May 15 | $623 |
Winter Haven Flight Information
Traveling to | Winter Haven |
|---|---|
Lowest Price | $76 |
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 May 5 to May 6
$95 total
May 5 - May 6
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. ...
Budget Inn Winter Haven
401 6th Street HWY 17N Winter Haven FL
$83 nightly
The price is $93 total per night from May 8 to May 9
$93 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 (287 reviews)
There were no amenities with this hotel. It was clean, and staff was very pleasant and helpful. Was on busy road, which was alittle noisy.
Reviewed on May 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 May 24 to May 25
$90 total
May 24 - May 25
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 (277 reviews)
It says there’s a continental breakfast on here but there is none….i booked that room because it said there’s breakfast
Reviewed on Apr 30, 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 May 5 to May 6
$95 total
May 5 - May 6
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. ...
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
$98 nightly
The price is $110 total per night from Jun 3 to Jun 4
$110 total
Jun 3 - Jun 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)
Gran espacio, muy limpio excelente vista
Reviewed on Apr 26, 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 May 5 to May 6
$95 total
May 5 - May 6
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. ...
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
$98 nightly
The price is $110 total per night from Jun 3 to Jun 4
$110 total
Jun 3 - Jun 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)
Gran espacio, muy limpio excelente vista
Reviewed on Apr 26, 2026
Hampton Inn Winter Haven
202 Cypress Gardens Blvd Winter Haven FL
$138 nightly
The price is $154 total per night from May 11 to May 12
$154 total
May 11 - May 12
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)
The breakfast menu was very good. Excellent variety. Staff was very friendly. Room was clean. Didn't go swimming. Rooms were quiet. Bed was so comfortable. Slept like a baby. LOL
Reviewed on Apr 28, 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 May 24 to May 25
$90 total
May 24 - May 25
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 (277 reviews)
It says there’s a continental breakfast on here but there is none….i booked that room because it said there’s breakfast
Reviewed on Apr 30, 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 tripsWinter Haven flight + hotel packages - first class flights
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View all tripsNeed a Car For After Your Flight?
Compact
Tampa, USA
$7
$13 total
found 2 days ago
Economy
Tampa, USA
$7
$13 total
found 2 days ago
Standard
Tampa, Florida, USA
$7
$19 total
found 1 day ago
Special
Tampa, Florida, USA
$9
$30 total
found 2 days ago
Lowest prices found within the past 2 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
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Winter Haven Vacation Rentals
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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
Activities, attractions and tours
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