Cheap Flights to Winter Haven from $29
Wander Wisely with exceptional service, 24/7 supportOpens in a new window
Feel at ease with free flight cancellations within 24 hours of booking
Change your flight without a fee on select flights
How Much Does it Cost To Fly To Winter Haven?
The cheapest prices found with in the last 7 days for return flights were $56 and $29 for one-way flights to Winter Haven for the period specified. Prices and availability are subject to change. Additional terms apply
ATL
Hartsfield-Jackson Atlanta Intl.
TPA
Tampa Intl.
$56 Roundtrip, found 8 hours ago
$56
Roundtrip
found 8 hours ago
CLE
Hopkins Intl.
TPA
Tampa Intl.
$88 Roundtrip, found 19 hours ago
$88
Roundtrip
found 19 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| TTN | Tampa | June 3 to August 12 | $88 |
| CLE | Tampa | August 11 to August 11 | $93 |
| SWF | Tampa | August 19 to October 10 | $171 |
| MDW | Tampa | June 17 to June 24 | $185 |
| ORD | Tampa | June 30 to July 15 | $190 |
| DTW | Tampa | July 8 to July 12 | $194 |
| BOS | Tampa | July 14 to July 21 | $200 |
| EWR | Tampa | June 16 to June 24 | $200 |
| MSP | Tampa | August 6 to August 7 | $207 |
| YYZ | Tampa | August 8 to August 9 | $266 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| CLE | Tampa | May 24 to June 7 | $168 |
| LGA | Tampa | May 24 to May 27 | $253 |
| PHL | Tampa | May 24 to May 30 | $275 |
| ORD | Tampa | May 24 to May 24 | $288 |
| ORD | Tampa | May 24 to May 24 | $288 |
| BOS | Tampa | May 24 to June 2 | $297 |
| MSP | Tampa | May 24 to May 30 | $317 |
| DTW | Tampa | May 24 to May 28 | $349 |
| EWR | Tampa | May 23 to May 27 | $383 |
| YYZ | Tampa | May 22 to May 25 | $872 |
Winter Haven Flight Information
Traveling to | Winter Haven |
|---|---|
Lowest Price | $56 |
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
1300 3rd St Winter Haven FL
$85 nightly
The price is $95 total per night from May 18 to May 19
$95 total
May 18 - May 19
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! (1,011 reviews)
Everything about this property was wonderful. We enjoyed our stay very much!
Reviewed on May 11, 2026
Budget Inn Winter Haven
401 6th Street HWY 17N Winter Haven FL
$83 nightly
The price is $93 total per night from May 16 to May 17
$93 total
May 16 - May 17
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 (287 reviews)
There were no amenities with this hotel. It was clean, and staff was very pleasant and helpful. Was on busy road, which was alittle noisy.
Reviewed on May 1, 2026
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 May 16 to May 17
$95 total
May 16 - May 17
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 (279 reviews)
The cost not worth the price. Did not like 150 deposit for the check in.
Reviewed on May 10, 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 May 18 to May 19
$95 total
May 18 - May 19
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! (1,011 reviews)
Everything about this property was wonderful. We enjoyed our stay very much!
Reviewed on May 11, 2026
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
$98 nightly
The price is $110 total per night from Jun 3 to Jun 4
$110 total
Jun 3 - Jun 4
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)
Gran espacio, muy limpio excelente vista
Reviewed on Apr 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 May 18 to May 19
$95 total
May 18 - May 19
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! (1,011 reviews)
Everything about this property was wonderful. We enjoyed our stay very much!
Reviewed on May 11, 2026
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
$98 nightly
The price is $110 total per night from Jun 3 to Jun 4
$110 total
Jun 3 - Jun 4
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)
Gran espacio, muy limpio excelente vista
Reviewed on Apr 26, 2026
Hampton Inn Winter Haven
202 Cypress Gardens Blvd Winter Haven FL
$115 nightly
The price is $128 total per night from Jun 7 to Jun 8
$128 total
Jun 7 - Jun 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 ...
9/10 Wonderful! (1,001 reviews)
Clean room, friendly & professional staff.
Reviewed on May 10, 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
$85 nightly
The price is $95 total per night from May 16 to May 17
$95 total
May 16 - May 17
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 (279 reviews)
The cost not worth the price. Did not like 150 deposit for the check in.
Reviewed on May 10, 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.
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?
Economy
Tampa, USA
$5
$10 total
found 12 hours ago
Standard
Tampa, USA
$5
$10 total
found 12 hours ago
Midsize
Tampa, USA
$7
$13 total
found 12 hours ago
Compact
Tampa, USA
$7
$13 total
found 12 hours ago
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.
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
Explore More Ways to Travel with Travelocity
- Orlando Hotels
- B&B in Eloise
- Cabins in Eloise
- Condos in Eloise
- Eloise Hotels
- Motels in Eloise
- Hotels near Inman Park
- Hotels near LEGOLAND® Florida
- Hotels near Indigo's Billiards
- Hotels near Rotary Park
- Motels in Winter Haven Station
- Hotels near Northgate Shopping Center
- Hotels near Theatre Winter Haven
- Hotels near Chain Of Wakes
- Holiday Park Resorts in Cypress Gardens
- Cheap Hotels in Cypress Gardens
- Pet Friendly Hotels in Cypress Gardens
- Lodges in Cypress Gardens
- Motels in Cypress Gardens
- Resorts in Cypress Gardens
- Hotels near Baytree Golf Club
- Hotels near Winter Haven Municipal
- Hotels near Sertoma Park
- Jan Phyl Village Hotels
- Cabins in Auburndale
- Condos in Auburndale
- Cottages in Auburndale
- Extended Stay Hotels in Auburndale
- Guest Houses in Auburndale
- Hostels in Auburndale
- Cheap Hotels in Auburndale
- Pet Friendly Hotels in Auburndale
- Auburndale Hotels
- Houseboats in Auburndale
- Motels in Auburndale
- Vacation Homes in Auburndale
- Villas in Auburndale
- 5 Star Hotels in Eagle Lake
- Apartments in Eagle Lake
- B&B in Eagle Lake
- Cabins in Eagle Lake
- Condos in Eagle Lake
- Cottages in Eagle Lake
- Eagle Lake Hotels
- Houseboats in Eagle Lake
- Vacation Homes in Eagle Lake
- Rv Parks in Eagle Lake
- Resorts in Eagle Lake
- Hotels near Willowbrook Golf Course
- Flights to Orlando
- Flights to Tampa
- Flights to Celebration
- Flights to Lithia
- Flights to Lakeland - Winter Haven
- Flights to Lakeland
- Flights to Crystal Springs
- Flights to Avon Park
- Flights to Zephyrhills
- Flights to Lake Buena Vista
- Flights to Haines City
- Flights to Lake Wales
- Flights to Dover
- Flights to Waverly
- Flights to Valrico
- Flights to Fort Meade
- Flights to Lake Alfred
- Flights to Frostproof
- Flights to Kissimmee
- Flights from Winter Haven Municipal
- Flights to Lake Buena Vista North
- Flights to Plant City
- Flights to Champions Gate
- Flights to Four Corners
- Flights to Poinciana
- Flights to Florida
- Flights to Central Florida
- Flights to Bartow
- Flights to Auburndale
- Flights to Davenport