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 $44 and $39 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.
$44 Roundtrip, found 18 hours ago
$44
Roundtrip
found 18 hours ago
ILG
New Castle
TPA
Tampa Intl.
$99 Roundtrip, found 10 hours ago
$99
Roundtrip
found 10 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| PHL | Tampa | December 5 to December 8 | $56 |
| CLE | Tampa | October 24 to October 31 | $57 |
| PHL | St. Petersburg - Clearwater | October 2 to October 5 | $78 |
| DTW | Tampa | December 3 to December 9 | $82 |
| ORD | Tampa | December 4 to December 13 | $141 |
| ORD | Tampa | December 4 to December 13 | $141 |
| MSP | Tampa | October 27 to October 31 | $148 |
| RFD | St. Petersburg - Clearwater | October 30 to November 2 | $151 |
| SWF | Tampa | September 30 to October 3 | $153 |
| SWF | St. Petersburg - Clearwater | November 1 to November 5 | $156 |
| DTW | Lakeland | December 7 to December 14 | $164 |
| BOS | Tampa | November 3 to November 7 | $179 |
| YYZ | Tampa | October 18 to October 25 | $180 |
| EWR | Tampa | November 10 to November 18 | $211 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| MDW | Tampa | September 12 to October 12 | $267 |
| SWF | Tampa | September 12 to November 4 | $283 |
| TTN | Tampa | September 13 to September 14 | $305 |
| SWF | St. Petersburg - Clearwater | September 13 to September 20 | $315 |
| YYZ | Tampa | September 12 to September 20 | $318 |
| CLE | Tampa | September 12 to September 15 | $338 |
| MSP | Tampa | September 12 to October 22 | $345 |
| ORD | Tampa | September 12 to September 14 | $365 |
| DTW | Tampa | September 12 to September 13 | $375 |
| BOS | Tampa | September 12 to September 18 | $516 |
| EWR | Tampa | September 13 to September 15 | $576 |
Winter Haven Flight Information
Traveling to | Winter Haven |
|---|---|
Lowest Price | $44 |
Number of Airlines Serving | |
Airlines Serving | Allegiant Air, Frontier Airlines, Avelo 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 Sep 12 to Sep 13
$95 total
Sep 12 - Sep 13
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
$76 nightly
The price is $86 total per night from Oct 9 to Oct 10
$86 total
Oct 9 - Oct 10
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 ...
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 Sep 12 to Sep 13
$90 total
Sep 12 - Sep 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 (289 reviews)
"Ok yo stay one night, the receptionist veo helpful and friendly. No breakfast offered, even we paid for"
Reviewed on Sep 7, 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 Sep 12 to Sep 13
$95 total
Sep 12 - Sep 13
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
$87 nightly
The price is $97 total per night from Sep 13 to Sep 14
$97 total
Sep 13 - Sep 14
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)
"My wife and her sister stayed the first night which was fine, so I booked a second night ,the breakfast are free but you have to paid a 50.00 to use the utensils nonrefundable so breakfast isn't free however please take note that you are responsible for washing the dishware that you have chosen to ..."
Reviewed on Aug 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 Sep 12 to Sep 13
$95 total
Sep 12 - Sep 13
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
$87 nightly
The price is $97 total per night from Sep 13 to Sep 14
$97 total
Sep 13 - Sep 14
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)
"My wife and her sister stayed the first night which was fine, so I booked a second night ,the breakfast are free but you have to paid a 50.00 to use the utensils nonrefundable so breakfast isn't free however please take note that you are responsible for washing the dishware that you have chosen to ..."
Reviewed on Aug 26, 2026
Hampton Inn Winter Haven
202 Cypress Gardens Blvd Winter Haven FL
$114 nightly
The price is $128 total per night from Sep 20 to Sep 21
$128 total
Sep 20 - Sep 21
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)
"We checked and stayed 3 nights the first night we discovered we had a leak under the bathroom sink and the light socket in the bathroom was broken also we told the front desk the next morning they said no maintenance was on duty to fix it . The next morning told them again they never fixed it. They ..."
Reviewed on Sep 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
$81 nightly
The price is $90 total per night from Sep 12 to Sep 13
$90 total
Sep 12 - Sep 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 (289 reviews)
"Ok yo stay one night, the receptionist veo helpful and friendly. No breakfast offered, even we paid for"
Reviewed on Sep 7, 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.
Winter Haven flight + hotel packages - first class flights
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
See all available trips from New York to Winter Haven
View all tripsNeed a Car For After Your Flight?
Standard
Tampa, USA
$5
$10 total
found 7 hours ago
Midsize
Tampa, USA
$6
$11 total
found 7 hours ago
Compact SUV
Tampa, USA
$7
$13 total
found 7 hours ago
Economy
TAMPA, USA
$7
$14 total
found 7 hours ago
Lowest prices found within the past 7 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
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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