Cheap Flights to Winter Haven
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| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| PHL | Tampa | September 6 to October 1 | $76 |
| CLE | Tampa | July 13 to July 22 | $119 |
| SWF | Tampa | August 26 to September 2 | $149 |
| MDW | Tampa | June 30 to July 7 | $171 |
| MSP | Tampa | August 24 to September 1 | $187 |
| DTW | Tampa | September 5 to September 19 | $199 |
| EWR | Tampa | August 22 to August 29 | $207 |
| ORD | Tampa | July 8 to July 29 | $209 |
| BOS | Tampa | August 12 to August 17 | $234 |
| YYZ | Tampa | September 4 to September 7 | $317 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| PHL | Tampa | June 6 to June 13 | $169 |
| SWF | Tampa | June 6 to June 13 | $216 |
| CLE | Tampa | June 7 to July 27 | $225 |
| YYZ | Tampa | June 6 to June 8 | $278 |
| MDW | Tampa | June 6 to June 23 | $317 |
| ORD | Tampa | June 7 to June 16 | $350 |
| BOS | Tampa | June 7 to June 12 | $400 |
| DTW | Tampa | June 5 to June 8 | $408 |
| EWR | Tampa | June 5 to June 10 | $408 |
| MSP | Tampa | June 7 to June 13 | $429 |
Winter Haven Flight Information
Traveling to | Winter Haven |
|---|---|
Lowest Price | $76 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines, Breeze Airways, Southwest Airlines, Sun Country Airlines, Delta, American Airlines, WestJet |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Amazing Winter Haven Accommodation Deals
Howard Johnson by Wyndham Winter Haven FL
1300 3rd St Winter Haven FL
$85 nightly
The price is $95 total per night from Jun 3 to Jun 4
$95 total
Jun 3 - Jun 4
Total with taxes and fees
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! (1,007 reviews)
"Well I didn't look at the pictures good enough because if I did, there's no way I would had booked this room. There are tile floors, room has a mold/mildew odor coming from it. Bottom of the bed looks like it's dirty. Tub had what appeared to be rust or mold. Very old outdated hotel. Even the comforter ..."
Reviewed on Jun 1, 2026
Budget Inn Winter Haven
401 6th Street HWY 17N Winter Haven FL
$83 nightly
The price is $93 total per night from Jun 2 to Jun 3
$93 total
Jun 2 - Jun 3
Total with taxes and fees
Stay at this motel in Winter Haven. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions LEGOLAND® Florida and Winter Haven Public Library ...
6.8/10 (291 reviews)
"I enjoyed my stay, would stay again"
Reviewed on Jun 1, 2026
Rodeway Inn & Suites Winter Haven Chain Of Lakes
1911 Cypress Gardens Blvd Winter Haven FL
$72 nightly
The price is $81 total per night from Jun 30 to Jul 1
$81 total
Jun 30 - Jul 1
Total with taxes and fees
Book a stay at this business-friendly motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LEGOLAND® Florida and Peppa ...
5.2/10 (281 reviews)
"this hotel is in a very poor condition they advertise free breakfast but they stopped serving it. The lights in the room did not work. No shampoo. The bed is noisy and the air matress is on very bad condition."
Reviewed on May 30, 2026
Save an average of 15% on thousands of hotels when you're signed in
Winter Haven Gardens Inn
1150 3rd Street SW Winter Haven FL
Stay at this hotel in Winter Haven. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions LEGOLAND® Florida and Indigo's Family Fun Center ...
5.8/10 (1,000 reviews)
Booked a hotel that was permanently closed
"Didn't stay. Got here and sign on door saying permanent closed. Had to find somewhere else to stay at last minute. Good thing other family members had extra room and allowed us to stay with them."
Reviewed on Dec 18, 2022
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.
Luxury Hotels in Winter Haven
Howard Johnson by Wyndham Winter Haven FL
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! (1,007 reviews)
"Well I didn't look at the pictures good enough because if I did, there's no way I would had booked this room. There are tile floors, room has a mold/mildew odor coming from it. Bottom of the bed looks like it's dirty. Tub had what appeared to be rust or mold. Very old outdated hotel. Even the comforter ..."
Reviewed on Jun 1, 2026
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
Book a stay at this beach hotel in Winter Haven. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
7/10 Good! (1,000 reviews)
"Gran espacio, muy limpio excelente vista"
Reviewed on Apr 26, 2026
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.
Family Friendly Hotels in Winter Haven
Howard Johnson by Wyndham Winter Haven FL
1300 3rd St Winter Haven FL
$85 nightly
The price is $95 total per night from Jun 3 to Jun 4
$95 total
Jun 3 - Jun 4
Total with taxes and fees
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! (1,007 reviews)
"Well I didn't look at the pictures good enough because if I did, there's no way I would had booked this room. There are tile floors, room has a mold/mildew odor coming from it. Bottom of the bed looks like it's dirty. Tub had what appeared to be rust or mold. Very old outdated hotel. Even the comforter ..."
Reviewed on Jun 1, 2026
Lake Roy Beach Inn
1823 Cypress Gardens Blvd Winter Haven FL
$98 nightly
The price is $110 total per night from Jun 2 to Jun 3
$110 total
Jun 2 - Jun 3
Total with taxes and fees
Book a stay at this beach hotel in Winter Haven. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
7/10 Good! (1,000 reviews)
"Gran espacio, muy limpio excelente vista"
Reviewed on Apr 26, 2026
Hampton Inn Winter Haven
202 Cypress Gardens Blvd Winter Haven FL
$115 nightly
The price is $128 total per night from Jun 7 to Jun 8
$128 total
Jun 7 - Jun 8
Total with taxes and fees
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 ...
9/10 Wonderful! (1,004 reviews)
"Great location, so many restaurants within walking distance. The staff were friendly and helpful. Breakfast was plentiful and varied."
Reviewed on May 29, 2026
Save an average of 15% on thousands of hotels when you're signed in
Rodeway Inn & Suites Winter Haven Chain Of Lakes
1911 Cypress Gardens Blvd Winter Haven FL
$72 nightly
The price is $81 total per night from Jun 30 to Jul 1
$81 total
Jun 30 - Jul 1
Total with taxes and fees
Book a stay at this business-friendly motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LEGOLAND® Florida and Peppa ...
5.2/10 (281 reviews)
"this hotel is in a very poor condition they advertise free breakfast but they stopped serving it. The lights in the room did not work. No shampoo. The bed is noisy and the air matress is on very bad condition."
Reviewed on May 30, 2026
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.
Best Winter Haven Flight and Hotel Packages
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View all tripsNeed a Car For After Your Flight?
Economy
Tampa, USA
$6
$11 total
found 1 day ago
Midsize
Tampa, USA
$7
$13 total
found 1 day ago
Compact
Tampa, USA
$7
$13 total
found 1 day ago
Standard
Tampa, USA
$7
$13 total
found 1 day ago
Flights To Winter Haven
Situated within striking range of both Orlando and Tampa, Winter Haven is a popular spot within Central Florida, as the combo of amusement parks, picturesque natural areas, excellent water skiing spots, and laid-back atmosphere make it a place where you can have fun without feeling in a rush. Hence, it's a true Florida town. If you plan on getting here via air, you're in luck too, as you can choose to land at either Orlando International Airport (MCO) or Tampa International Airport (TPA).
Transportation from TPA and MCO
If you've found some great deals for Winter Haven flights landing at Tampa International Airport, know you'll be roughly 57 miles from the city when you arrive. Thus, your best option is to rent a car in the baggage claim area, though you could catch a taxi outside the baggage claim level, or book a shuttle van. If you've discovered some good flights to Winter Haven that land at Orlando International Airport, know you'll be roughly 48 miles from the city when you arrive. Hence, your most convenient option is to also get a rental vehicle, which can be arranged on the ground transportation level of any terminal at MCO. It is possible to take a public bus from MCO to Winter Haven, but there are numerous transfers, and it's very time consuming. After all, you'll want to drop your bags off at your choice of Winter Haven hotels and go explore as quick as possible.
Experience Winter Haven
Enjoy the rides at Legoland Florida, and fish at Lake Hamilton while in Winter Haven. If you want to find discount plane tickets and hotel rooms for Winter Haven, look no further than Travelocity. We offer a price match guarantee, which means that if you find cheaper airfare to Winter Haven or lower cost packages to Winter Haven elsewhere, we'll match that price and refund the difference.
More Ways To Wander
Winter Haven Hotels
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Things to do in Winter Haven
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