Cheap Flights to Winter Haven from $29
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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 $58 and $29 for one-way flights to Winter Haven for the period specified. Prices and availability are subject to change. Additional terms apply
ATL
Hartsfield-Jackson Atlanta Intl.
TPA
Tampa Intl.
$58 Roundtrip, found 2 hours ago
$58
Roundtrip
found 2 hours ago
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$86 Roundtrip, found 6 hours ago
$86
Roundtrip
found 6 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| PHL | Tampa | May 30 to June 6 | $88 |
| CLE | Tampa | July 14 to July 22 | $98 |
| SWF | Tampa | May 30 to June 3 | $133 |
| MDW | Tampa | May 26 to May 28 | $164 |
| ORD | Tampa | June 30 to November 5 | $186 |
| DTW | Tampa | June 3 to June 10 | $195 |
| BOS | Tampa | May 20 to May 23 | $202 |
| MSP | Tampa | June 28 to July 3 | $202 |
| EWR | Tampa | June 9 to June 11 | $203 |
| YYZ | Tampa | June 23 to July 8 | $260 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| CLE | Tampa | May 8 to May 19 | $195 |
| TTN | Tampa | May 9 to May 16 | $244 |
| SWF | Tampa | May 9 to May 16 | $268 |
| YYZ | Tampa | May 10 to May 15 | $273 |
| MDW | Tampa | May 9 to May 10 | $297 |
| ORD | Tampa | May 8 to May 10 | $310 |
| DTW | Tampa | May 9 to May 11 | $352 |
| MSP | Tampa | May 10 to May 18 | $367 |
| EWR | Tampa | May 10 to May 13 | $405 |
| BOS | Tampa | May 9 to May 12 | $467 |
Winter Haven Flight Information
Traveling to | Winter Haven |
|---|---|
Lowest Price | $58 |
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 7 to May 8
$95 total
May 7 - May 8
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! (1,004 reviews)
Breakfast so poor
Reviewed on May 3, 2026
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 25 to May 26
$90 total
May 25 - May 26
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 7 to May 8
$95 total
May 7 - May 8
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! (1,004 reviews)
Breakfast so poor
Reviewed on May 3, 2026
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 7 to May 8
$95 total
May 7 - May 8
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! (1,004 reviews)
Breakfast so poor
Reviewed on May 3, 2026
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! (1,001 reviews)
The breakfast was great! Staff ever efficient. Parking was great! The room was clean and very comfortable! I really enjoyed my stay! Good location too! Overall amazing value and would definitely stay again.
Reviewed on May 3, 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 25 to May 26
$90 total
May 25 - May 26
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.
Winter Haven flight + hotel packages - premium economy flights
Price found within the past 48 hours. Click for updated prices.
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See all available trips from Philadelphia 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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See all available trips from New York to Winter Haven
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
$18 total
found 9 hours ago
Midsize
Tampa, Florida, USA
$7
$18 total
found 9 hours 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
Find the perfect hotel after your flight
Winter Haven Vacation Rentals
Great Deals on alternative accommodations
Winter Haven Car Rentals
Affordable cars to get you around town
Winter Haven Vacations
Save more by combining flights, hotels and cars
Things to do in Winter Haven
Activities, attractions and tours
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