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Winter Haven

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Winter Haven Flights as Low as $148

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Frontier Airlines
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Sun Country Airlines
Frontier Airlines
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Frontier Airlines
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Delta
American Airlines
United
Alaska Airlines
Sun Country Airlines
Sun Country Airlines
Sun Country Airlines

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 February, 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 16 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 $148, 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 $148 right now, why wait?

Winter Haven Flight Information
Destination airport
Tampa Intl.
Destination airport IATA code
TPA
Roundtrip price
$148

Last Minute Hotel Deals 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
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. ...
7/10 Good! (1,014 reviews)
Front deak staff was very polite and efficient. The room was okay, could have been cleaner, there were cigarette bitts all over the patio outside and some garbage left in the room.

Reviewed on Jan 27, 2026

Howard Johnson by Wyndham Winter Haven FL
LEGOLAND Beach Retreat

LEGOLAND Beach Retreat

3 out of 5
100 Legoland Way SE Winter Haven FL
Stay at this hotel in Winter Haven. Enjoy free breakfast, parking (surcharge), and a 24-hour front desk. Popular attractions LEGOLAND® Florida and Peppa Pig ...
9/10 Wonderful! (156 reviews)
Everything was perfect!!!! Cool crisp blankets wonderful pillows, clean room and bathroom!! Loved everything!!

Reviewed on Jan 25, 2026

LEGOLAND Beach Retreat
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! (64 reviews)
Perfect for young kids

Reviewed on Jan 27, 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! (8,993 reviews)
My young son and I loved the resort! The waterpark, pools, and hot tub were our favorite features. We loved the arcade and indoor mini golf too. The grounds were well maintained, and we enjoyed the lake and courtyard views. The two bedroom condo was spacious and clean. We also enjoyed the meal options ...

Reviewed on Feb 1, 2026

The Grove Resort & Water Park Orlando
Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

3 out of 5
2975 Arabian Nights Blvd Kissimmee FL
Book a stay at this family-friendly condo in Kissimmee. Enjoy free WiFi, 7 outdoor pools, and 7 hot tubs. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (3,275 reviews)
First time staying there. Loved everything about the property

Reviewed on Feb 2, 2026

Vacation Village Orlando, Celebration
Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

3 out of 5
5711 W Irlo Bronson Memorial Hwy Kissimmee FL
Book a stay at this family-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.2/10 Very Good! (2,219 reviews)
Clean Room , Great Staff , Awesome Breakfast

Reviewed on Jan 29, 2026

Holiday Inn & Suites Orlando SW - Celebration Area by IHG
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! (2,564 reviews)
My son and I loved the pool, lazy river, and outdoor mini golf. We also enjoyed the free breakfast. The staff were friendly and helpful!

Reviewed on Feb 1, 2026

Kompose Boutique Resort at Theme Parks
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! (2,586 reviews)
Absolutely lovely. Huge space. Clean and bright. Easy parking

Reviewed on Jan 30, 2026

Holiday Inn Club Vacations at Orange Lake Resort by IHG
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.