Cheap Flight Deals to Winter Haven FL from CA $91

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How to find cheap flights to Winter Haven?

The cheapest prices found with in the last 7 days for return flights were CA $91 and CA $91 for one-way flights to Winter Haven for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
BOSTampaMarch 24 to April 1CA $91
DTWTampaMay 6 to May 13CA $104
ORDTampaMarch 30 to April 5CA $113
ORDTampaMarch 30 to April 5CA $113
PHLTampaMarch 24 to April 4CA $133
CLETampaMarch 30 to April 5CA $138
JFKTampaMarch 29 to April 3CA $168
MSPTampaApril 19 to April 29CA $201
EWRTampaApril 1 to April 4CA $207
YYZTampaApril 4 to April 15CA $234
MSPSt. Petersburg - ClearwaterApril 24 to April 24CA $255
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
BOSTampaMarch 23 to April 2CA $142
CLETampaMarch 23 to April 4CA $210
YYZTampaMarch 23 to March 28CA $243
EWRTampaMarch 23 to April 5CA $287
EWRTampaMarch 23 to April 5CA $287
DTWTampaMarch 22 to March 27CA $373
MSPTampaMarch 21 to March 25CA $404
ORDTampaMarch 21 to March 31CA $448
ORDTampaMarch 21 to March 31CA $448
*Prices include taxes and fees

Your guide to flights to Winter Haven, FL

Spirit Airlines, Porter Airlines, Delta fly to Winter Haven, so use Travelocity to search, find, and compare some truly tempting deals from the 4 airlines—that way you can be sure you’ve found the best deal for you. A flight to Winter Haven FL currently costs between CA $91 and CA $448. Prices vary, but for the best fares, travel in April when prices are at their lowest.  

Top tips for finding cheap flights to Winter Haven  

The cheapest flight for a round trip to Winter Haven is currently CA $91. When you search for flights to Winter Haven, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Winter Haven for nearby days.  The cheapest month to travel to Winter Haven is April from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to Winter Haven 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to Winter Haven with Travelocity 

We have top deals on plane tickets even for last minute flights to Winter Haven, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Winter Haven for less. 

Find The Perfect Hotel For After Your Flight

Amazing Place to Stay After Flight to Winter Haven

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St, SW, Winter Haven, FL
The price is CA $159 per night from Apr. 6 to Apr. 7
CA $159
CA $178 total
includes taxes & fees
6 Apr - 7 Apr
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 (1,004 reviews)
"Need a bigger TV in room"

Reviewed on 14 Mar. 2025

Howard Johnson by Wyndham Winter Haven FL
Budget Inn Winter Haven

Budget Inn Winter Haven

2 out of 5
401 6th Street HWY 17N, Winter Haven, FL
The price is CA $136 per night from Mar. 16 to Mar. 17
CA $136
CA $153 total
includes taxes & fees
16 Mar - 17 Mar
Stay at this motel in Winter Haven. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions LEGOLAND® Florida and Indigo's Family Fun Center ...
6.6/10 (244 reviews)
"Room was clean. It is a non smoking facility, but vaguely smelled of cigarettes."

Reviewed on 5 Mar. 2025

Budget Inn Winter Haven
Rodeway Inn & Suites Winter Haven Chain Of Lakes

Rodeway Inn & Suites Winter Haven Chain Of Lakes

2 out of 5
1911 Cypress Gardens Blvd, Winter Haven, FL
The price is CA $151 per night from Mar. 16 to Mar. 17
CA $151
CA $169 total
includes taxes & fees
16 Mar - 17 Mar
Book a stay at this business-friendly motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LEGOLAND® Florida and Baytree ...
5.4/10 (234 reviews)
"I like the staff. They call me when I didn’t check in and I find out that I made a mistake on the day on my reservation. I didn’t like that it show in the link that they have free breakfast and that did not include."

Reviewed on 10 Sep. 2024

Rodeway Inn & Suites Winter Haven Chain Of Lakes
Save an average of 15% on thousands of hotels when you're signed in
Winter Haven Gardens Inn

Winter Haven Gardens Inn

2.5 out of 5
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 18 Dec. 2022

Winter Haven Gardens Inn
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

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St, SW, Winter Haven, FL
The price is CA $159 per night from Apr. 6 to Apr. 7
CA $159
CA $178 total
includes taxes & fees
6 Apr - 7 Apr
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 (1,004 reviews)
"Need a bigger TV in room"

Reviewed on 14 Mar. 2025

Howard Johnson by Wyndham Winter Haven FL
Lake Roy Beach Inn

Lake Roy Beach Inn

2 out of 5
1823 Cypress Gardens Blvd, Winter Haven, FL
The price is CA $198 per night from Mar. 19 to Mar. 20
CA $198
CA $222 total
includes taxes & fees
19 Mar - 20 Mar
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 ...
6.8/10 (939 reviews)
"The location was excellent. Just an 8 minute drive from Legoland. Lots of food options nearby, iHop just a minute away, Denny’s 5 minutes, and a few minutes more Chipotle, McDonald’s, etc. The hotel itself is old, but everything functioned. Room had a fridge, microwave, coffeemaker, tv. Everything ..."

Reviewed on 13 Mar. 2025

Lake Roy Beach Inn
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

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St, SW, Winter Haven, FL
The price is CA $159 per night from Apr. 6 to Apr. 7
CA $159
CA $178 total
includes taxes & fees
6 Apr - 7 Apr
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 (1,004 reviews)
"Need a bigger TV in room"

Reviewed on 14 Mar. 2025

Howard Johnson by Wyndham Winter Haven FL
Lake Roy Beach Inn

Lake Roy Beach Inn

2 out of 5
1823 Cypress Gardens Blvd, Winter Haven, FL
The price is CA $198 per night from Mar. 19 to Mar. 20
CA $198
CA $222 total
includes taxes & fees
19 Mar - 20 Mar
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 ...
6.8/10 (939 reviews)
"The location was excellent. Just an 8 minute drive from Legoland. Lots of food options nearby, iHop just a minute away, Denny’s 5 minutes, and a few minutes more Chipotle, McDonald’s, etc. The hotel itself is old, but everything functioned. Room had a fridge, microwave, coffeemaker, tv. Everything ..."

Reviewed on 13 Mar. 2025

Lake Roy Beach Inn
Hampton Inn Winter Haven

Hampton Inn Winter Haven

2.5 out of 5
202 Cypress Gardens Blvd, Winter Haven, FL
The price is CA $182 per night from Apr. 6 to Apr. 7
CA $182
CA $204 total
includes taxes & fees
6 Apr - 7 Apr
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 ...
8.8/10 Excellent! (1,001 reviews)
Bedtime
"Bed needs help. Not the most comfortable"

Reviewed on 12 Mar. 2025

Hampton Inn Winter Haven
Save an average of 15% on thousands of hotels when you're signed in
Rodeway Inn & Suites Winter Haven Chain Of Lakes

Rodeway Inn & Suites Winter Haven Chain Of Lakes

2 out of 5
1911 Cypress Gardens Blvd, Winter Haven, FL
The price is CA $151 per night from Mar. 16 to Mar. 17
CA $151
CA $169 total
includes taxes & fees
16 Mar - 17 Mar
Book a stay at this business-friendly motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LEGOLAND® Florida and Baytree ...
5.4/10 (234 reviews)
"I like the staff. They call me when I didn’t check in and I find out that I made a mistake on the day on my reservation. I didn’t like that it show in the link that they have free breakfast and that did not include."

Reviewed on 10 Sep. 2024

Rodeway Inn & Suites Winter Haven Chain Of Lakes
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

Winter Haven flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites
Ocean Club Treasure Island Hotel
The Avalon Club
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Winter Haven flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
Kompose Boutique Hotel
voco Sarasota by IHG
Carlisle Inn
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Need a car after flight to Winter Haven?

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.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.