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Winter Haven

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Cheap Flights to Winter Haven

Fall in love at first flight with your vacation to Winter Haven by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Winter Haven on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Winter Haven, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Winter Haven

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Winter Haven with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the TPA airport.

What is the cheapest month to fly to Winter Haven?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Winter Haven are in , but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Winter Haven?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find  to choose from for your flight to Winter Haven.

What airport is best to fly into Winter Haven?

When you’re planning your trip to Winter Haven, convenience is the name of the game. Luckily, Winter Haven Lakeland Intl. Airport Airport is nearby so you can deplane and get going on checking off everything on your Winter Haven must-do list.

How much are flights to Winter Haven?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winter Haven on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as , you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Winter Haven?

The trick to saving a stack of cash on your flight to Winter Haven? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as  right now, why wait?

Winter Haven Flight Information
Destination airport
Tampa Intl.
Destination airport IATA code
TPA
Airlines serving
Alaska Airlines, American Airlines, Delta, Hawaiian Airlines, United
Number of airlines serving
5
Roundtrip price
$357
Popular airline
Delta

Last Minute Hotel Deals in Winter Haven

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 

3.5 out of 5
5801 Roosevelt Dr Winter Haven FL
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 ...
9.4/10 Exceptional! (1,106 reviews)
Clean

Reviewed on Jan 5, 2026

Best Western Plus Winter Haven Inn & Suites 
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way Winter Haven FL
Stay at this hotel in Winter Haven. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Popular attractions LEGOLAND® Florida and Peppa Pig Theme Park Florida ...
8.8/10 Excellent! (58 reviews)
Location, theming, activities were amazing

Reviewed on Jan 3, 2026

Legoland Florida Hotel
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
8/10 Very Good! (8,892 reviews)
Everything was great!!!!

Reviewed on Jan 2, 2026

The Grove Resort & Water Park Orlando
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3 out of 5
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
Stay at this resort in Kissimmee. Enjoy free WiFi, 2 hot tubs, and 2 outdoor pickleball courts. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN ...
9.4/10 Exceptional! (2,160 reviews)
Not bad

Reviewed on Jan 1, 2026

Kompose Boutique Resort at Theme Parks
Margaritaville Resort Orlando

Margaritaville Resort Orlando

4 out of 5
8000 Fins Up Circle Kissimmee FL
Book a stay at this spa resort in Kissimmee. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. ...
8.8/10 Excellent! (3,637 reviews)
The resort is top notch! Staff is great the location is awesome! Will definitely be back in the future!!

Reviewed on Jan 2, 2026

Margaritaville Resort Orlando
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

4 out of 5
7600 Mystic Dunes Lane Kissimmee FL
Book a stay at this golf property in Kissimmee. Enjoy free WiFi, free parking, and 4 outdoor pools. Our guests praise the pool and the restaurant in our reviews. ...
9/10 Wonderful! (4,547 reviews)
Clean and comfortable stay. My family enjoyed our rooms. The workers were friendly. The resort was more for younger aged children (the pool went only to 3 feet and the slide was not built for older kids) but overall, it made for a nice vacation for our family of 5.

Reviewed on Jan 1, 2026

Hilton Vacation Club Mystic Dunes Orlando
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

4 out of 5
8505 W Irlo Bronson Memorial Hwy Kissimmee FL
Book a stay at this golf resort in Kissimmee. Enjoy free WiFi, free parking, and 7 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (2,541 reviews)
Nuestra estadía fue muy buena,nuestra villa estaba limpia ,cómoda ,completa para pasar varios días ,piscinas limpias ,personal amable ,lo único q no me gustó fue la insistencia del personal para agendarme un recorrido para venderme un tiempo compartido,cuando pague un precio completo ,no me gusto ...

Reviewed on Jan 2, 2026

Holiday Inn Club Vacations at Orange Lake Resort by IHG
Comfort Inn & Suites Kissimmee by the Parks

Comfort Inn & Suites Kissimmee by the Parks

2.5 out of 5
7675 W Irlo Bronson Hwy Kissimmee FL
Stay at this hotel in Kissimmee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
7/10 Good! (2,107 reviews)
Me and my family really loved our stay. The highlight was the staff and the breakfast. The staff were very helpful and nice. The hot breakfast was great which consisted of Micky waffles, sausages, eggs, and hash browns. There were also other things such as cereal yogurt, etc. The free shuttles to ...

Reviewed on Jan 2, 2026

Comfort Inn & Suites Kissimmee by the Parks
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.