Cheap Flights to Winter Haven from $49

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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 $49 for one-way flights to Winter Haven for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
TTNTampaMay 18 to May 23$76
CLETampaJune 17 to June 19$109
DTWTampaJune 9 to June 14$126
LGATampaJune 2 to June 9$139
ORDTampaMay 10 to May 19$153
ORDTampaMay 10 to May 19$153
BOSTampaJune 2 to June 6$177
EWRTampaMay 12 to May 12$180
MSPTampaJune 30 to July 12$197
YYZTampaJune 1 to June 2$225
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
CLETampaMay 3 to May 5$162
ORDTampaMay 2 to May 10$165
ORDTampaMay 2 to May 10$165
TTNTampaMay 2 to May 7$175
LGATampaMay 1 to May 18$255
DTWTampaMay 2 to May 6$256
EWRTampaMay 1 to May 5$262
MSPTampaMay 1 to May 4$306
BOSTampaMay 2 to May 9$318
YYZTampaMay 3 to May 7$689
*Prices include taxes and fees

Winter Haven Flight Information

Traveling to
Winter Haven
Lowest Price
$76
Number of Airlines Serving
Airlines Serving
Frontier Airlines, Spirit 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

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St Winter Haven FL
$85 nightly
The price is $95 total per night from May 3 to May 4
$95 total
May 3 - May 4
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! (1,005 reviews)
Horrible breakfast all else great

Reviewed on Apr 27, 2026

Opens in a new windowHoward Johnson by Wyndham Winter Haven FL
Budget Inn Winter Haven

Budget Inn Winter Haven

2 out of 5
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 (286 reviews)
Había mucho ruido en la calle, la gente pasaba y no nos dejaban dormir

Reviewed on Apr 23, 2026

Opens in a new windowBudget Inn Winter Haven
Rodeway Inn & Suites Winter Haven Chain Of Lakes

Rodeway Inn & Suites Winter Haven Chain Of Lakes

2 out of 5
1911 Cypress Gardens Blvd Winter Haven FL
$85 nightly
The price is $95 total per night from Apr 29 to Apr 30
$95 total
Apr 29 - Apr 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 ...
5.4/10 (276 reviews)
Horrible experience overall, spider webs everywhere, breakfast was not included as advertised on the website, no shampoo available.

Reviewed on Apr 27, 2026

Opens in a new windowRodeway Inn & Suites Winter Haven Chain Of Lakes
Save an average of 15% on thousands of hotels when you're signed in
Winter Haven Gardens Inn

Winter Haven Gardens Inn

2.5 out of 5
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

Opens in a new windowWinter Haven Gardens Inn
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

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St Winter Haven FL
$85 nightly
The price is $95 total per night from May 3 to May 4
$95 total
May 3 - May 4
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! (1,005 reviews)
Horrible breakfast all else great

Reviewed on Apr 27, 2026

Opens in a new windowHoward Johnson by Wyndham Winter Haven FL
Lake Roy Beach Inn

Lake Roy Beach Inn

2 out of 5
1823 Cypress Gardens Blvd Winter Haven FL
$108 nightly
The price is $121 total per night from Apr 29 to Apr 30
$121 total
Apr 29 - Apr 30
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! (1,005 reviews)
Gran espacio, muy limpio excelente vista

Reviewed on Apr 26, 2026

Opens in a new windowLake Roy Beach Inn
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

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St Winter Haven FL
$85 nightly
The price is $95 total per night from May 3 to May 4
$95 total
May 3 - May 4
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! (1,005 reviews)
Horrible breakfast all else great

Reviewed on Apr 27, 2026

Opens in a new windowHoward Johnson by Wyndham Winter Haven FL
Lake Roy Beach Inn

Lake Roy Beach Inn

2 out of 5
1823 Cypress Gardens Blvd Winter Haven FL
$108 nightly
The price is $121 total per night from Apr 29 to Apr 30
$121 total
Apr 29 - Apr 30
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! (1,005 reviews)
Gran espacio, muy limpio excelente vista

Reviewed on Apr 26, 2026

Opens in a new windowLake Roy Beach Inn
Hampton Inn Winter Haven

Hampton Inn Winter Haven

2.5 out of 5
202 Cypress Gardens Blvd Winter Haven FL
$115 nightly
The price is $128 total per night from May 10 to May 11
$128 total
May 10 - May 11
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 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

Opens in a new windowHampton Inn Winter Haven
Save an average of 15% on thousands of hotels when you're signed in
Rodeway Inn & Suites Winter Haven Chain Of Lakes

Rodeway Inn & Suites Winter Haven Chain Of Lakes

2 out of 5
1911 Cypress Gardens Blvd Winter Haven FL
$85 nightly
The price is $95 total per night from Apr 29 to Apr 30
$95 total
Apr 29 - Apr 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 ...
5.4/10 (276 reviews)
Horrible experience overall, spider webs everywhere, breakfast was not included as advertised on the website, no shampoo available.

Reviewed on Apr 27, 2026

Opens in a new windowRodeway Inn & Suites Winter Haven Chain Of Lakes
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.
Mar Bay Motel &Suites
Cedar Cove Resort and Cottages
Ocean Club Treasure Island Hotel
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See all available trips from Boston to Winter Haven
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Winter Haven flight + hotel packages - business class flights

Price found within the past 48 hours. Click for updated prices.
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
Hyatt House Tampa Downtown
Hyatt Place Tampa Downtown
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See all available trips from Minneapolis to Winter Haven
View all trips

Winter Haven flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel
Cedar Cove Resort and Cottages
Ocean Club Treasure Island Hotel
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See all available trips from Boston to Winter Haven
View all trips

Need a Car For After Your Flight?

Lowest prices found within the past 12 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.

Explore More Ways to Travel with Travelocity

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.