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Winter Haven

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Winter Haven Flights as Low as $167

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

Breeze Airways
Fri, Jul 10 - Tue, Jul 14
HVN
Tweed - New Haven Regional
TPA
Tampa Intl.
$167 Roundtrip, found 9 hours ago
$167
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Fri, Jul 10 from Tweed - New Haven Regional to Tampa Intl., returning Tue, Jul 14, priced at $167 found 9 hours ago
Breeze Airways
Fri, Jul 10 - Tue, Jul 14
HVN
Tweed - New Haven Regional
TPA
Tampa Intl.
$172 Roundtrip, found 9 hours ago
$172
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Fri, Jul 10 from Tweed - New Haven Regional to Tampa Intl., returning Tue, Jul 14, priced at $172 found 9 hours ago
Avelo Airlines
Wed, Jul 1 - Fri, Jul 3
HVN
Tweed - New Haven Regional
TPA
Tampa Intl.
$174 Roundtrip, found 6 days ago
$174
Roundtrip
found 6 days ago
Select Avelo Airlines flight, departing Wed, Jul 1 from Tweed - New Haven Regional to Tampa Intl., returning Fri, Jul 3, priced at $174 found 6 days ago
Avelo Airlines
Fri, Jul 10 - Sun, Jul 12
HVN
Tweed - New Haven Regional
LAL
Lakeland Intl. Airport
$176 Roundtrip, found 10 hours ago
$176
Roundtrip
found 10 hours ago
Select Avelo Airlines flight, departing Fri, Jul 10 from Tweed - New Haven Regional to Lakeland Intl. Airport, returning Sun, Jul 12, priced at $176 found 10 hours ago
Breeze Airways
Fri, Jul 10 - Tue, Jul 14
HVN
Tweed - New Haven Regional
TPA
Tampa Intl.
$177 Roundtrip, found 9 hours ago
$177
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Fri, Jul 10 from Tweed - New Haven Regional to Tampa Intl., returning Tue, Jul 14, priced at $177 found 9 hours ago
Avelo Airlines
Fri, Jul 3 - Fri, Jul 10
HVN
Tweed - New Haven Regional
TPA
Tampa Intl.
$179 Roundtrip, found 6 days ago
$179
Roundtrip
found 6 days ago
Select Avelo Airlines flight, departing Fri, Jul 3 from Tweed - New Haven Regional to Tampa Intl., returning Fri, Jul 10, priced at $179 found 6 days ago
Avelo Airlines
Fri, Jul 10 - Mon, Jul 13
HVN
Tweed - New Haven Regional
LAL
Lakeland Intl. Airport
$186 Roundtrip, found 4 days ago
$186
Roundtrip
found 4 days ago
Select Avelo Airlines flight, departing Fri, Jul 10 from Tweed - New Haven Regional to Lakeland Intl. Airport, returning Mon, Jul 13, priced at $186 found 4 days ago
Avelo Airlines
Fri, Jul 10 - Sun, Jul 12
HVN
Tweed - New Haven Regional
LAL
Lakeland Intl. Airport
$192 Roundtrip, found 1 day ago
$192
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Fri, Jul 10 from Tweed - New Haven Regional to Lakeland Intl. Airport, returning Sun, Jul 12, priced at $192 found 1 day ago
Avelo Airlines
Mon, Jul 27 - Mon, Aug 3
HVN
Tweed - New Haven Regional
LAL
Lakeland Intl. Airport
$194 Roundtrip, found 6 days ago
$194
Roundtrip
found 6 days ago
Select Avelo Airlines flight, departing Mon, Jul 27 from Tweed - New Haven Regional to Lakeland Intl. Airport, returning Mon, Aug 3, priced at $194 found 6 days ago
Breeze Airways
Tue, Jun 30 - Fri, Jul 3
HVN
Tweed - New Haven Regional
TPA
Tampa Intl.
$204 Roundtrip, found 6 days ago
$204
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Tue, Jun 30 from Tweed - New Haven Regional to Tampa Intl., returning Fri, Jul 3, priced at $204 found 6 days ago
Avelo Airlines
Wed, Jul 1 - Fri, Jul 3
HVN
Tweed - New Haven Regional
TPA
Tampa Intl.
$207 Roundtrip, found 13 hours ago
$207
Roundtrip
found 13 hours ago
Select Avelo Airlines flight, departing Wed, Jul 1 from Tweed - New Haven Regional to Tampa Intl., returning Fri, Jul 3, priced at $207 found 13 hours ago
Breeze Airways
Tue, Jun 30 - Fri, Jul 3
HVN
Tweed - New Haven Regional
TPA
Tampa Intl.
$209 Roundtrip, found 6 days ago
$209
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Tue, Jun 30 from Tweed - New Haven Regional to Tampa Intl., returning Fri, Jul 3, priced at $209 found 6 days ago
Avelo Airlines
Mon, Jul 27 - Mon, Aug 3
HVN
Tweed - New Haven Regional
LAL
Lakeland Intl. Airport
$212 Roundtrip, found 4 days ago
$212
Roundtrip
found 4 days ago
Select Avelo Airlines flight, departing Mon, Jul 27 from Tweed - New Haven Regional to Lakeland Intl. Airport, returning Mon, Aug 3, priced at $212 found 4 days ago
Breeze Airways
Mon, Jun 29 - Fri, Jul 3
HVN
Tweed - New Haven Regional
TPA
Tampa Intl.
$214 Roundtrip, found 6 days ago
$214
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Mon, Jun 29 from Tweed - New Haven Regional to Tampa Intl., returning Fri, Jul 3, priced at $214 found 6 days ago
Breeze Airways
Tue, Jun 30 - Fri, Jul 3
HVN
Tweed - New Haven Regional
TPA
Tampa Intl.
$214 Roundtrip, found 6 days ago
$214
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Tue, Jun 30 from Tweed - New Haven Regional to Tampa Intl., returning Fri, Jul 3, priced at $214 found 6 days ago
Breeze Airways
Mon, Jun 29 - Tue, Jul 7
HVN
Tweed - New Haven Regional
TPA
Tampa Intl.
$226 Roundtrip, found 6 days ago
$226
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Mon, Jun 29 from Tweed - New Haven Regional to Tampa Intl., returning Tue, Jul 7, priced at $226 found 6 days ago

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 July, 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 $167, 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 $167 right now, why wait?

Winter Haven Flight Information
Destination airport
Tampa Intl.
Destination airport IATA code
TPA
Roundtrip price
$76

Last Minute Hotel Deals in Winter Haven

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

3 out of 5
200 Cypress Gardens Boulevard Winter Haven FL
Book a stay at this business-friendly hotel in Winter Haven. Enjoy free WiFi, free parking, and room service. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,011 reviews)
"Breakfast isn't included, which wasn't clear on booking"

Reviewed on Jun 8, 2026

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Holiday Inn Winter Haven by IHG
Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG

3 out of 5
305 5th St NW and Avenue D NW Winter Haven FL
Stay at this hotel in Winter Haven. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.8/10 Exceptional! (813 reviews)
"Great hotel, the rooms were clean the staff was helpful, very family friendly!"

Reviewed on Jun 7, 2026

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Staybridge Suites Winter Haven Auburndale by IHG
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. ...
7.4/10 Good! (1,015 reviews)
"No me gusto el aire acondicionado fatal. Toda la noche tumbando y un ruido terrible dejaba de enfriar.Mas no me limpiaron la habitación al menos recojer la basura. Los matress estan de cambiar."

Reviewed on Jun 8, 2026

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Howard Johnson by Wyndham Winter Haven FL
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! (1,292 reviews)
"Good breakfast"

Reviewed on Jun 9, 2026

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Best Western Plus Winter Haven Inn & Suites 
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 ...
8.8/10 Excellent! (256 reviews)
"I loved that this property was so family friendly. My kids loved how “on-theme” it was. Lego everywhere! They even got a free small Lego set on their pillows upon checking in. The pool was great, with a fire pit and you could purchase smores kits for nighttime at the fire pit. It felt very safe as ..."

Reviewed on Jun 9, 2026

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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! (129 reviews)
"Best hotel to stay when visiting Legoland. On the expensive side, but it is worth it."

Reviewed on Jun 4, 2026

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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! (10,174 reviews)
"Wonderful"

Reviewed on Jun 10, 2026

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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! (4,364 reviews)
"The property, staff ,amenities, cleanliness’s was great. The only issue we had is that having to have the same hot breakfast for 5 days. Maybe consider having a pancake day, French toast day or even an omelette day, besides the repeated breakfast, no complains. Would most definitely be booking with ..."

Reviewed on Jun 10, 2026

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Kompose Boutique Resort at Theme Parks
See all 37,864 properties in Winter Haven
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.