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Winter Haven

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Winter Haven Flights as Low as $64

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

Frontier Airlines
Wed, Feb 12 - Wed, Feb 12
BOS
Logan Intl.
TPA
Tampa Intl.
$64 Roundtrip, found 1 day ago
$64
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Feb 12 from Logan Intl. to Tampa Intl., returning Wed, Feb 12, priced at $64 found 1 day ago
Spirit Airlines
Sun, Feb 9 - Wed, Feb 12
BOS
Logan Intl.
TPA
Tampa Intl.
$66 Roundtrip, found 1 day ago
$66
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Feb 9 from Logan Intl. to Tampa Intl., returning Wed, Feb 12, priced at $66 found 1 day ago
Frontier Airlines
Sun, Feb 9 - Wed, Feb 12
BOS
Logan Intl.
TPA
Tampa Intl.
$71 Roundtrip, found 1 day ago
$71
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Feb 9 from Logan Intl. to Tampa Intl., returning Wed, Feb 12, priced at $71 found 1 day ago
Spirit Airlines
Sun, Feb 9 - Wed, Feb 12
BOS
Logan Intl.
TPA
Tampa Intl.
$71 Roundtrip, found 1 day ago
$71
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Feb 9 from Logan Intl. to Tampa Intl., returning Wed, Feb 12, priced at $71 found 1 day ago
Frontier Airlines
Wed, Feb 12 - Thu, Feb 13
BOS
Logan Intl.
TPA
Tampa Intl.
$76 Roundtrip, found 1 day ago
$76
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Feb 12 from Logan Intl. to Tampa Intl., returning Thu, Feb 13, priced at $76 found 1 day ago
Frontier Airlines
Wed, Feb 12 - Sat, Feb 22
ORD
O'Hare Intl.
TPA
Tampa Intl.
$77 Roundtrip, found 22 hours ago
$77
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Wed, Feb 12 from O'Hare Intl. to Tampa Intl., returning Sat, Feb 22, priced at $77 found 22 hours ago
Spirit Airlines
Sat, Feb 22 - Thu, Feb 27
BOS
Logan Intl.
TPA
Tampa Intl.
$78 Roundtrip, just found
$78
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Feb 22 from Logan Intl. to Tampa Intl., returning Thu, Feb 27, priced at $78 just found
Frontier Airlines
Sat, Feb 22 - Thu, Feb 27
BOS
Logan Intl.
TPA
Tampa Intl.
$83 Roundtrip, just found
$83
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Feb 22 from Logan Intl. to Tampa Intl., returning Thu, Feb 27, priced at $83 just found
Frontier Airlines
Sat, Feb 15 - Sat, Feb 22
ORD
O'Hare Intl.
TPA
Tampa Intl.
$84 Roundtrip, found 22 hours ago
$84
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Sat, Feb 15 from O'Hare Intl. to Tampa Intl., returning Sat, Feb 22, priced at $84 found 22 hours ago
Spirit Airlines
Thu, Feb 27 - Mon, Mar 10
BOS
Logan Intl.
TPA
Tampa Intl.
$88 Roundtrip, found 20 hours ago
$88
Roundtrip
found 20 hours ago
Select Spirit Airlines flight, departing Thu, Feb 27 from Logan Intl. to Tampa Intl., returning Mon, Mar 10, priced at $88 found 20 hours ago
Frontier Airlines
Wed, Feb 19 - Tue, Feb 25
BOS
Logan Intl.
TPA
Tampa Intl.
$88 Roundtrip, just found
$88
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Feb 19 from Logan Intl. to Tampa Intl., returning Tue, Feb 25, priced at $88 just found
JetBlue Airways
Sat, Feb 22 - Thu, Feb 27
BOS
Logan Intl.
TPA
Tampa Intl.
$137 Roundtrip, just found
$137
Roundtrip
just found
Select JetBlue Airways flight, departing Sat, Feb 22 from Logan Intl. to Tampa Intl., returning Thu, Feb 27, priced at $137 just found
Delta
Tue, Feb 11 - Wed, Feb 12
BOS
Logan Intl.
TPA
Tampa Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Feb 11 from Logan Intl. to Tampa Intl., returning Wed, Feb 12, priced at $137 found 1 day ago
United
Tue, Feb 18 - Wed, Feb 19
ORD
O'Hare Intl.
TPA
Tampa Intl.
$157 Roundtrip, found 5 days ago
$157
Roundtrip
found 5 days ago
Select United flight, departing Tue, Feb 18 from O'Hare Intl. to Tampa Intl., returning Wed, Feb 19, priced at $157 found 5 days ago
American Airlines
Tue, Feb 18 - Wed, Feb 19
ORD
O'Hare Intl.
TPA
Tampa Intl.
$157 Roundtrip, found 5 days ago
$157
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Feb 18 from O'Hare Intl. to Tampa Intl., returning Wed, Feb 19, priced at $157 found 5 days ago
Spirit Airlines
Tue, Mar 11 - Wed, Mar 12
ROC
Greater Rochester Intl.
TPA
Tampa Intl.
$160 Roundtrip, found 19 hours ago
$160
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Tue, Mar 11 from Greater Rochester Intl. to Tampa Intl., returning Wed, Mar 12, priced at $160 found 19 hours 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 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 $64, 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 $64 right now, why wait?

Winter Haven Flight Information
Destination airport
Tampa Intl.
Destination airport IATA code
TPA
Roundtrip price
$139

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
The price is $139 per night from Jan 29 to Jan 30
$139
includes taxes & fees
Jan 29 - Jan 30
Stay at this 3.5-star 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! (673 reviews)
"Everything was great with the exception of the eggs at breakfast. They are circular egg patties and they are the worst egg I have ever tasted. Best western should consider going back to scrambled eggs."

Reviewed on Jan 20, 2025

Best Western Plus Winter Haven Inn & Suites 
Howard Johnson by Wyndham Winter Haven FL
Howard Johnson by Wyndham Winter Haven FL
2 out of 5
1300 3rd St Sw, Cypress Gardens & US 17 South, Winter Haven, FL
The price is $114 per night from Jan 26 to Jan 27
$114
includes taxes & fees
Jan 26 - Jan 27
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! (1,004 reviews)
"Nice property at a nice price. Friendly staff"

Reviewed on Jan 19, 2025

Howard Johnson by Wyndham Winter Haven FL
Holiday Inn Winter Haven, an IHG Hotel
Holiday Inn Winter Haven, an IHG Hotel
3 out of 5
200 Cypress Gardens Boulevard, Winter Haven, FL
The price is $124 per night from Jan 26 to Jan 27
$124
includes taxes & fees
Jan 26 - Jan 27
Stay at this 3-star business-friendly hotel in Winter Haven. Enjoy free WiFi, free parking, and room service. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,004 reviews)
"Beautiful area with a variety of restaurants to choose from. Hotel is very clean and staff are friendly"

Reviewed on Jan 17, 2025

Holiday Inn Winter Haven, an IHG Hotel
The Grove Resort & Water Park Orlando
The Grove Resort & Water Park Orlando
4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
The price is $211 per night from Jan 23 to Jan 24
$211
includes taxes & fees
Jan 23 - Jan 24
Stay at this 4-star spa resort in Four Corners. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
8/10 Very Good! (6,744 reviews)
"Very good"

Reviewed on Jan 21, 2025

The Grove Resort & Water Park Orlando
Hilton Vacation Club Mystic Dunes Orlando
Hilton Vacation Club Mystic Dunes Orlando
7600 Mystic Dunes Lane, Kissimmee, FL
The price is $140 per night from Jan 29 to Jan 30
$140
includes taxes & fees
Jan 29 - Jan 30
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. ...
8.8/10 Excellent! (3,525 reviews)
"Easy check-in and checkout"

Reviewed on Jan 21, 2025

Hilton Vacation Club Mystic Dunes Orlando
Margaritaville Resort Orlando
Margaritaville Resort Orlando
4 out of 5
8000 Fins Up Circle, Kissimmee, FL
The price is $217 per night from Jan 26 to Jan 27
$217
includes taxes & fees
Jan 26 - Jan 27
Stay at this 4-star spa resort in Kissimmee. Enjoy 3 outdoor pools, a full-service spa, and 3 restaurants. Our guests praise the pool and the restaurant in our ...
8.8/10 Excellent! (3,194 reviews)
"Friendly and helpful staff, delicious dining, and channeling the spirit of Jimmy Buffett -- a wonderful experience!"

Reviewed on Jan 21, 2025

Margaritaville Resort Orlando
Hilton Vacation Club Aqua Sol Orlando West
Hilton Vacation Club Aqua Sol Orlando West
4 out of 5
17777 Bali Blvd, Winter Garden, FL
The price is $155 per night from Jan 29 to Jan 30
$155
includes taxes & fees
Jan 29 - Jan 30
Stay at this 4-star family-friendly hotel in Four Corners. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff ...
8.6/10 Excellent! (3,763 reviews)
"Excellent !"

Reviewed on Jan 20, 2025

Hilton Vacation Club Aqua Sol Orlando West
Delta Hotels by Marriott Orlando Celebration
Delta Hotels by Marriott Orlando Celebration
3.5 out of 5
2900 Parkway Blvd, Kissimmee, FL
The price is $123 per night from Jan 26 to Jan 27
$123
includes taxes & fees
Jan 26 - Jan 27
Stay at this 3.5-star business-friendly hotel in Kissimmee. Enjoy free WiFi, 2 outdoor pools, and 4 restaurants. Our guests praise the pool and the helpful staff ...
8/10 Very Good! (1,477 reviews)
"Great location, needed to attend competitions at ESPN Wide World of Sports each day. Lobby is great, open, clean, bar and restaurant very good. Outdoor pool/bar and property very pretty well cared for. Our guest room needed to be painted. Stains on ceiling and wall. Thank you! Enjoyed our stay. Would ..."

Reviewed on Jan 21, 2025

Delta Hotels by Marriott Orlando Celebration
See all 38,024 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.