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Winter Haven

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Winter Haven Flights as Low as $108

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

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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 May, 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 $108, 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 $108 right now, why wait?

Winter Haven Flight Information
Destination airport
Tampa Intl.
Destination airport IATA code
TPA
Roundtrip price
$196

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. ...
7.2/10 Good! (1,002 reviews)
Rooms smelled like mold.

Reviewed on Mar 12, 2026

Howard Johnson by Wyndham Winter Haven FL
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 ...
9/10 Wonderful! (88 reviews)
We stayed here for the convenience of location to Legoland. Our room was the Adventure room. It was at the very end of the hallway and looked like it hadn't been used in awhile. The shelves were dusty and the bathtub even had dust in it. The room was pretty dark. The bed was relatively comfortable. ...

Reviewed on Mar 9, 2026

Legoland Florida Hotel
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! (177 reviews)
Excellent breakfast fun kid environment!

Reviewed on Mar 15, 2026

LEGOLAND Beach Retreat
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! (9,144 reviews)
Great place to enjoy family and friends!

Reviewed on Mar 15, 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 breakfast, free WiFi, and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World ...
9.4/10 Exceptional! (3,111 reviews)
The reason for all the good reviews is that they give you a free snack at check in. So reviews are before people even see their room. Breakfast was horrible. Room smelled musty and not exactly clean. Very sterile. Wouldn’t stay there again

Reviewed on Mar 15, 2026

Kompose Boutique Resort at Theme Parks
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! (3,614 reviews)
We had a pretty busy week in Orlando planned so we didn't use much of the resorts amenities, but the room was excellent. Clean, well maintained, lots of space, and a great value for what we paid. Spacious bathroom, good kitchen area, and nice screened in patio. I would definitely stay here again. ...

Reviewed on Mar 15, 2026

Vacation Village Orlando, Celebration
Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

3 out of 5
7470 W. Irlo Bronson Memorial Hwy. Kissimmee FL
Book a stay at this business-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff ...
8/10 Very Good! (3,903 reviews)
Great location. Rooms are ok not the best but not the worst

Reviewed on Mar 15, 2026

Ramada by Wyndham Kissimmee Gateway
Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

3.5 out of 5
3011 Maingate Ln Kissimmee FL
Book a stay at this family-friendly hotel in Kissimmee. Enjoy free parking, 2 outdoor pools, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,395 reviews)
Pool had great hours, conveniently located, very comfortable beds

Reviewed on Mar 15, 2026

Holiday Inn Resort Kissimmee by the Parks 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.