Cheap Flights to Winter Haven from $35

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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 $68 and $35 for one-way flights to Winter Haven for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
PHLTampaJanuary 31 to January 31$68
ORDTampaJanuary 18 to January 31$68
ORDTampaJanuary 18 to January 31$68
JFKTampaJanuary 6 to January 14$68
DTWTampaJanuary 9 to January 12$76
CLETampaJanuary 19 to January 27$88
EWRTampaFebruary 3 to February 9$127
BOSTampaDecember 13 to December 17$139
MSPSt. Petersburg - ClearwaterFebruary 9 to February 13$167
MSPTampaJanuary 7 to January 14$167
YYZTampaJanuary 6 to January 16$170
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
CLETampaDecember 5 to December 12$112
DTWTampaDecember 7 to December 15$122
PHLTampaDecember 7 to December 10$147
LGATampaDecember 5 to December 11$150
EWRTampaDecember 6 to December 10$162
ORDTampaDecember 7 to December 10$205
ORDTampaDecember 7 to December 10$205
MSPTampaDecember 7 to December 11$211
YYZTampaDecember 7 to December 15$246
BOSTampaDecember 5 to December 8$268
*Prices include taxes and fees

Winter Haven Flight Information

Traveling to
Winter Haven
Lowest Price
$68
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 Nov 29 to Nov 30
$95 total
Nov 29 - Nov 30
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. ...
6.8/10 (1,007 reviews)
Check in was smooth. Room is fine. Clean but has a slight hint of smoke despite being a non-smoking room. Comfortable bed and nice shower.

Reviewed on Nov 18, 2025

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 Nov 30 to Dec 1
$93 total
Nov 30 - Dec 1
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 (268 reviews)
Friendly professional

Reviewed on Nov 14, 2025

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 Nov 29 to Nov 30
$95 total
Nov 29 - Nov 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 ...
5.2/10 (251 reviews)
No table and chairs, and No couch or living room chair, 1 swivel chair with some counter space near the television. No light over the sink for the bathroom. Other than these few items, a very pleasant, quiet stay.

Reviewed on Oct 11, 2025

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 ...
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 Nov 29 to Nov 30
$95 total
Nov 29 - Nov 30
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. ...
6.8/10 (1,007 reviews)
Check in was smooth. Room is fine. Clean but has a slight hint of smoke despite being a non-smoking room. Comfortable bed and nice shower.

Reviewed on Nov 18, 2025

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
$93 nightly
The price is $105 total per night from Dec 4 to Dec 5
$105 total
Dec 4 - Dec 5
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 (981 reviews)
clean room

Reviewed on Nov 6, 2025

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 Nov 29 to Nov 30
$95 total
Nov 29 - Nov 30
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. ...
6.8/10 (1,007 reviews)
Check in was smooth. Room is fine. Clean but has a slight hint of smoke despite being a non-smoking room. Comfortable bed and nice shower.

Reviewed on Nov 18, 2025

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
$93 nightly
The price is $105 total per night from Dec 4 to Dec 5
$105 total
Dec 4 - Dec 5
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 (981 reviews)
clean room

Reviewed on Nov 6, 2025

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
$95 nightly
The price is $107 total per night from Dec 7 to Dec 8
$107 total
Dec 7 - Dec 8
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! (1,005 reviews)
Yes

Reviewed on Nov 12, 2025

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 Nov 29 to Nov 30
$95 total
Nov 29 - Nov 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 ...
5.2/10 (251 reviews)
No table and chairs, and No couch or living room chair, 1 swivel chair with some counter space near the television. No light over the sink for the bathroom. Other than these few items, a very pleasant, quiet stay.

Reviewed on Oct 11, 2025

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.
Hilton Garden Inn Sarasota - Bradenton Airport
Mar Bay Motel &Suites
Hibiscus Suites - Gateway to Siesta Key
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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.
Hibiscus Suites - Gateway to Siesta Key
The Hotel Zamora
voco Sarasota by IHG
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See all available trips from Boston 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.
Wyndham Garden Tampa Fairgrounds/Casino
Saddlebrook Resort
Holiday Inn Express & Suites Trinity by IHG
Don't see what you're looking for?
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 20 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.