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
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$58 Roundtrip, found 1 hour ago
$58
Roundtrip
found 1 hour ago
MSP
Minneapolis - St. Paul Intl.
TPA
Tampa Intl.
$130 Roundtrip, found 2 days ago
$130
Roundtrip
found 2 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| PHL | Tampa | January 12 to January 21 | $58 |
| CLE | Tampa | January 19 to January 28 | $58 |
| DTW | Tampa | January 5 to January 15 | $59 |
| ORD | Tampa | February 15 to February 20 | $63 |
| ORD | Tampa | February 15 to February 20 | $63 |
| JFK | Tampa | January 7 to January 14 | $64 |
| BOS | Tampa | January 25 to January 31 | $119 |
| YYZ | Tampa | January 20 to January 21 | $153 |
| EWR | Tampa | January 19 to January 21 | $155 |
| MSP | St. Petersburg - Clearwater | February 9 to February 13 | $170 |
| MSP | St. Petersburg - Clearwater | February 9 to February 13 | $170 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| DTW | Tampa | January 4 to January 9 | $113 |
| CLE | Tampa | January 4 to January 9 | $135 |
| JFK | Tampa | January 4 to January 17 | $141 |
| PHL | Tampa | January 4 to January 9 | $151 |
| YYZ | Tampa | January 3 to January 10 | $267 |
| MSP | Tampa | January 3 to January 24 | $274 |
| BOS | Tampa | January 3 to January 17 | $297 |
| ORD | Tampa | January 3 to January 7 | $305 |
| ORD | Tampa | January 3 to January 7 | $305 |
| EWR | Tampa | January 2 to January 7 | $331 |
Winter Haven Flight Information
Traveling to | Winter Haven |
|---|---|
Lowest Price | $58 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines, Sun Country 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 Dec 30 to Dec 31
$95 total
Dec 30 - Dec 31
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. ...
7/10 Good! (1,002 reviews)
The only thing to note that is the smell no very good
Reviewed on Dec 28, 2025
Budget Inn Winter Haven
401 6th Street HWY 17N Winter Haven FL
$83 nightly
The price is $93 total per night from Dec 30 to Dec 31
$93 total
Dec 30 - Dec 31
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 ...
6.6/10 (271 reviews)
Good
Reviewed on Dec 21, 2025
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 Dec 30 to Dec 31
$95 total
Dec 30 - Dec 31
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 (253 reviews)
Great night
Reviewed on Nov 27, 2025
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 ...
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 Dec 30 to Dec 31
$95 total
Dec 30 - Dec 31
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. ...
7/10 Good! (1,002 reviews)
The only thing to note that is the smell no very good
Reviewed on Dec 28, 2025
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
$89 nightly
The price is $100 total per night from Jan 5 to Jan 6
$100 total
Jan 5 - Jan 6, 2026
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 ...
6.8/10 (990 reviews)
Everything was fine and staff very helpful.
Reviewed on Dec 26, 2025
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 Dec 30 to Dec 31
$95 total
Dec 30 - Dec 31
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. ...
7/10 Good! (1,002 reviews)
The only thing to note that is the smell no very good
Reviewed on Dec 28, 2025
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
$89 nightly
The price is $100 total per night from Jan 5 to Jan 6
$100 total
Jan 5 - Jan 6, 2026
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 ...
6.8/10 (990 reviews)
Everything was fine and staff very helpful.
Reviewed on Dec 26, 2025
Hampton Inn Winter Haven
202 Cypress Gardens Blvd Winter Haven FL
$106 nightly
The price is $118 total per night from Jan 4 to Jan 5
$118 total
Jan 4 - Jan 5, 2026
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 ...
8.8/10 Excellent! (1,002 reviews)
Very kind, friendly and helpful employees! Water pressure in shower was great! Beds were not as comfortable as some Hamptons. Would stay here again!
Reviewed on Dec 27, 2025
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 Dec 30 to Dec 31
$95 total
Dec 30 - Dec 31
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 (253 reviews)
Great night
Reviewed on Nov 27, 2025
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 Detroit to Winter Haven
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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 Newark Liberty Intl. Airport to Winter Haven
View all tripsNeed a Car For After Your Flight?
Midsize
Tampa, Florida, USA
$4
$8 total
found 1 day ago
Special
Tampa, Florida, USA
$4
$8 total
found 1 day ago
Compact
Tampa, Florida, USA
$4
$8 total
found 1 day ago
Economy
Tampa, Florida, USA
$4
$8 total
found 1 day 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
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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