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Winter Haven

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Winter Haven Flights as Low as $68

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

Frontier Airlines
Mon, Feb 24 - Thu, Feb 27
BOS
Logan Intl.
TPA
Tampa Intl.
$68 Roundtrip, found 10 hours ago
$68
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Mon, Feb 24 from Logan Intl. to Tampa Intl., returning Thu, Feb 27, priced at $68 found 10 hours ago
Frontier Airlines
Mon, Feb 24 - Fri, Feb 28
TTN
Mercer
TPA
Tampa Intl.
$68 Roundtrip, found 18 hours ago
$68
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Mon, Feb 24 from Mercer to Tampa Intl., returning Fri, Feb 28, priced at $68 found 18 hours ago
Frontier Airlines
Tue, Jan 7 - Thu, Jan 16
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$68 Roundtrip, found 5 hours ago
$68
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Jan 7 from Philadelphia Intl. to Tampa Intl., returning Thu, Jan 16, priced at $68 found 5 hours ago
Frontier Airlines
Sun, Jan 12 - Fri, Jan 24
BWI
Baltimore Washington Intl. Thurgood Marshall
TPA
Tampa Intl.
$68 Roundtrip, found 11 hours ago
$68
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Sun, Jan 12 from Baltimore Washington Intl. Thurgood Marshall to Tampa Intl., returning Fri, Jan 24, priced at $68 found 11 hours ago
Frontier Airlines
Sun, Feb 9 - Fri, Feb 14
BWI
Baltimore Washington Intl. Thurgood Marshall
TPA
Tampa Intl.
$73 Roundtrip, found 3 days ago
$73
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Feb 9 from Baltimore Washington Intl. Thurgood Marshall to Tampa Intl., returning Fri, Feb 14, priced at $73 found 3 days ago
Frontier Airlines
Sat, Jan 18 - Thu, Jan 30
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$74 Roundtrip, found 6 hours ago
$74
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sat, Jan 18 from Philadelphia Intl. to Tampa Intl., returning Thu, Jan 30, priced at $74 found 6 hours ago
Frontier Airlines
Mon, Feb 10 - Fri, Feb 14
BWI
Baltimore Washington Intl. Thurgood Marshall
TPA
Tampa Intl.
$78 Roundtrip, found 3 days ago
$78
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Feb 10 from Baltimore Washington Intl. Thurgood Marshall to Tampa Intl., returning Fri, Feb 14, priced at $78 found 3 days ago
Spirit Airlines
Fri, Feb 7 - Wed, Feb 12
BOS
Logan Intl.
TPA
Tampa Intl.
$78 Roundtrip, found 3 days ago
$78
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Fri, Feb 7 from Logan Intl. to Tampa Intl., returning Wed, Feb 12, priced at $78 found 3 days ago
Frontier Airlines
Mon, Feb 10 - Wed, Feb 19
BWI
Baltimore Washington Intl. Thurgood Marshall
TPA
Tampa Intl.
$83 Roundtrip, found 3 days ago
$83
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Feb 10 from Baltimore Washington Intl. Thurgood Marshall to Tampa Intl., returning Wed, Feb 19, priced at $83 found 3 days ago
Frontier Airlines
Mon, Jan 6 - Thu, Jan 9
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$85 Roundtrip, found 4 days ago
$85
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Jan 6 from Philadelphia Intl. to Tampa Intl., returning Thu, Jan 9, priced at $85 found 4 days ago
Frontier Airlines
Mon, Jan 13 - Mon, Jan 13
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$88 Roundtrip, found 2 days ago
$88
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Jan 13 from Philadelphia Intl. to Tampa Intl., returning Mon, Jan 13, priced at $88 found 2 days ago
JetBlue Airways
Thu, Feb 6 - Wed, Feb 12
BOS
Logan Intl.
TPA
Tampa Intl.
$129 Roundtrip, found 3 days ago
$129
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Thu, Feb 6 from Logan Intl. to Tampa Intl., returning Wed, Feb 12, priced at $129 found 3 days ago
Delta
Tue, Jan 7 - Sat, Jan 11
BOS
Logan Intl.
TPA
Tampa Intl.
$137 Roundtrip, found 20 hours ago
$137
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Jan 7 from Logan Intl. to Tampa Intl., returning Sat, Jan 11, priced at $137 found 20 hours ago
American Airlines
Fri, Jan 10 - Sun, Jan 12
BOS
Logan Intl.
TPA
Tampa Intl.
$158 Roundtrip, found 20 hours ago
$158
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Fri, Jan 10 from Logan Intl. to Tampa Intl., returning Sun, Jan 12, priced at $158 found 20 hours ago
Delta
Wed, Feb 12 - Mon, Feb 17
DCA
Ronald Reagan Washington National
TPA
Tampa Intl.
$167 Roundtrip, found 3 days ago
$167
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Feb 12 from Ronald Reagan Washington National to Tampa Intl., returning Mon, Feb 17, priced at $167 found 3 days ago
United
Mon, Jan 20 - Mon, Jan 27
BOS
Logan Intl.
TPA
Tampa Intl.
$186 Roundtrip, found 3 days ago
$186
Roundtrip
found 3 days ago
Select United flight, departing Mon, Jan 20 from Logan Intl. to Tampa Intl., returning Mon, Jan 27, priced at $186 found 3 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 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 Kissimmee Gateway 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 $68, 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 $68 right now, why wait?

Winter Haven Flight Information
Destination airport
Tampa Intl.
Destination airport IATA code
TPA
Roundtrip price
$138

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 $148 per night from Dec 24 to Dec 25
$148
includes taxes & fees
Dec 24 - Dec 25
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! (634 reviews)
"Everything was amazing"

Reviewed on Dec 20, 2024

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 Dec 26 to Dec 27
$114
includes taxes & fees
Dec 26 - Dec 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. ...
6.8/10 (1,003 reviews)
"Nice"

Reviewed on Dec 15, 2024

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 $140 per night from Jan 13 to Jan 14
$140
includes taxes & fees
Jan 13 - Jan 14, 2025
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! (1,001 reviews)
"One night stay so no chance to review all facilities. Room was a good size / comfy bed / good shower / friendly staff / easy parking / multiple eateries in easy walking distance. Good price."

Reviewed on Dec 19, 2024

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 $207 per night from Dec 24 to Dec 25
$207
includes taxes & fees
Dec 24 - Dec 25
Stay at this 4-star family-friendly resort in Four Corners. Enjoy free WiFi, 3 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
8/10 Very Good! (6,673 reviews)
"Excellent service clean fresh nice new awesome place to stay and I will stay there again I take my boyfriend there for his birthday and he loved it."

Reviewed on Dec 21, 2024

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 $132 per night from Jan 12 to Jan 13
$132
includes taxes & fees
Jan 12 - Jan 13, 2025
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! (3,421 reviews)
"I loved the suite. It had everything our family needed to feel like a home away from home."

Reviewed on Dec 22, 2024

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 $192 per night from Jan 5 to Jan 6
$192
includes taxes & fees
Jan 5 - Jan 6, 2025
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! (3,190 reviews)
"Loved it all!!!"

Reviewed on Dec 21, 2024

Margaritaville Resort Orlando
Ramada by Wyndham Kissimmee Gateway
Ramada by Wyndham Kissimmee Gateway
3 out of 5
7470 W. Irlo Bronson Memorial Hwy., Kissimmee, FL
The price is $81 per night from Jan 6 to Jan 7
$81
includes taxes & fees
Jan 6 - Jan 7, 2025
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 ...
7.6/10 Good! (4,040 reviews)
Prompt response and perfect place to lay your head
"We checked into our first room and my dad discovered his bed was broken when he sat down and fell off it. I went and let the front desk know immediately and they had no problem switching us quickly to a new room. This is my go to hotel for every Orlando trip so I highly recommend."

Reviewed on Dec 20, 2024

Ramada by Wyndham Kissimmee Gateway
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 $161 per night from Jan 4 to Jan 5
$161
includes taxes & fees
Jan 4 - Jan 5, 2025
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! (3,721 reviews)
"The rooms are spacious and in great condition! It has a full kitchen, living room, and dining area. Excellent for a family vacation!!"

Reviewed on Dec 19, 2024

Hilton Vacation Club Aqua Sol Orlando West
See all 37,996 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.