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 $60 and $38 for one-way flights to Winter Haven for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
DTWTampaSeptember 1 to September 9$60
TTNTampaOctober 5 to October 8$76
CLETampaAugust 31 to September 7$114
SWFTampaAugust 26 to September 2$122
EWRTampaOctober 3 to October 7$157
BOSTampaSeptember 8 to September 12$177
RFDTampaSeptember 9 to September 12$193
MSPTampaSeptember 6 to September 6$197
ORDTampaSeptember 14 to September 17$205
YYZTampaSeptember 4 to September 25$242
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
CLETampaJuly 10 to July 26$242
LGATampaJuly 10 to July 13$260
MSPTampaJuly 12 to July 18$286
TTNTampaJuly 12 to July 18$297
MDWTampaJuly 11 to July 18$322
ORDTampaJuly 11 to July 18$340
DTWTampaJuly 11 to July 12$357
EWRTampaJuly 10 to July 14$372
BOSTampaJuly 12 to July 16$425
YYZTampaJuly 12 to August 24$705
*Prices include taxes and fees

Winter Haven Flight Information

Traveling to
Winter Haven
Lowest Price
$60
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

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 Jul 6 to Jul 7
$95 total
Jul 6 - Jul 7
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. ...
7.4/10 Good! (1,000 reviews)
"Clean room and well maintained compared to others in this range. Close to Legoland. Not many breakfast options but thats not really a big deal. Overall pretty satisfied."

Reviewed on Jul 3, 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 Jul 5 to Jul 6
$93 total
Jul 5 - Jul 6
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 (292 reviews)
"I enjoyed my stay, would stay again"

Reviewed on Jun 1, 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
$81 nightly
The price is $90 total per night from Jul 26 to Jul 27
$90 total
Jul 26 - Jul 27
Total with taxes and fees
Book a stay at this business-friendly motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LEGOLAND® Florida and Peppa ...
5.4/10 (287 reviews)
"No continental breakfast, staff was late upon check in, it’s a 150$ deposit for an already dirty room. Multiple reasons for an uncomfortable stay."

Reviewed on Jul 1, 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 Jul 6 to Jul 7
$95 total
Jul 6 - Jul 7
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. ...
7.4/10 Good! (1,000 reviews)
"Clean room and well maintained compared to others in this range. Close to Legoland. Not many breakfast options but thats not really a big deal. Overall pretty satisfied."

Reviewed on Jul 3, 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
$98 nightly
The price is $110 total per night from Jul 7 to Jul 8
$110 total
Jul 7 - Jul 8
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! (1,001 reviews)
"You expect quaint. You get unsafe, unsanitary and rudeness. You realize from the check-in through a tiny gated slot that this is not going well. You climb the rickety stairs up and follow the uneven hallway down to the room and use your old fashioned door key to enter. Inside the room is extremely ..."

Reviewed on Jul 3, 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 Jul 6 to Jul 7
$95 total
Jul 6 - Jul 7
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. ...
7.4/10 Good! (1,000 reviews)
"Clean room and well maintained compared to others in this range. Close to Legoland. Not many breakfast options but thats not really a big deal. Overall pretty satisfied."

Reviewed on Jul 3, 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
$98 nightly
The price is $110 total per night from Jul 7 to Jul 8
$110 total
Jul 7 - Jul 8
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! (1,001 reviews)
"You expect quaint. You get unsafe, unsanitary and rudeness. You realize from the check-in through a tiny gated slot that this is not going well. You climb the rickety stairs up and follow the uneven hallway down to the room and use your old fashioned door key to enter. Inside the room is extremely ..."

Reviewed on Jul 3, 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
$107 nightly
The price is $120 total per night from Jul 26 to Jul 27
$120 total
Jul 26 - Jul 27
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)
"Awesome gym."

Reviewed on Jul 2, 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
$81 nightly
The price is $90 total per night from Jul 26 to Jul 27
$90 total
Jul 26 - Jul 27
Total with taxes and fees
Book a stay at this business-friendly motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LEGOLAND® Florida and Peppa ...
5.4/10 (287 reviews)
"No continental breakfast, staff was late upon check in, it’s a 150$ deposit for an already dirty room. Multiple reasons for an uncomfortable stay."

Reviewed on Jul 1, 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.
St Pete Beach Suites
CW Hotel
Cedar Cove Resort and Cottages
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See all available trips from Boston to Winter Haven
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Winter Haven flight + hotel packages - premium economy flights

Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Clearwater Beach
CW Hotel
The Avalon Club
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See all available trips from Minneapolis 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.
The Sarasota Modern, a Tribute Portfolio Hotel
Legacy Hotel at IMG Academy
Seaside at Anna Maria Island Inn
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See all available trips from Newark Liberty Intl. Airport to Winter Haven
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Need a Car For After Your Flight?

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.

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*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.