Cheap Flights To Winter Haven (GIF)

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Cheap Flights to Winter Haven from $46 One Way, $107 Round Trip

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

Wed, Sep 9 - Sat, Sep 12
ROC
Greater Rochester Intl.
TPA
Tampa Intl.
$107 Roundtrip, found 4 days ago
$107
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Sep 9 from Greater Rochester Intl. to Tampa Intl., returning Sat, Sep 12, priced at $107 found 4 days ago
Wed, Sep 23 - Sun, Sep 27
SJU
Luis Munoz Marin Intl.
TPA
Tampa Intl.
$108 Roundtrip, just found
$108
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Sep 23 from Luis Munoz Marin Intl. to Tampa Intl., returning Sun, Sep 27, priced at $108 just found
Thu, Oct 15 - Thu, Oct 22
HVN
Tweed - New Haven Regional
LAL
Lakeland Intl. Airport
$110 Roundtrip, found 14 hours ago
$110
Roundtrip
found 14 hours ago
Select Avelo Airlines flight, departing Thu, Oct 15 from Tweed - New Haven Regional to Lakeland Intl. Airport, returning Thu, Oct 22, priced at $110 found 14 hours ago
Sat, Sep 19 - Sat, Sep 26
ROC
Greater Rochester Intl.
TPA
Tampa Intl.
$112 Roundtrip, found 1 hour ago
$112
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Sep 19 from Greater Rochester Intl. to Tampa Intl., returning Sat, Sep 26, priced at $112 found 1 hour ago
Tue, Aug 25 - Tue, Sep 1
HVN
Tweed - New Haven Regional
TPA
Tampa Intl.
$116 Roundtrip, found 4 days ago
$116
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Tue, Aug 25 from Tweed - New Haven Regional to Tampa Intl., returning Tue, Sep 1, priced at $116 found 4 days ago
Sat, Sep 5 - Sat, Sep 12
ROC
Greater Rochester Intl.
TPA
Tampa Intl.
$118 Roundtrip, just found
$118
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Sep 5 from Greater Rochester Intl. to Tampa Intl., returning Sat, Sep 12, priced at $118 just found
Sat, Sep 12 - Sat, Sep 19
ROC
Greater Rochester Intl.
TPA
Tampa Intl.
$119 Roundtrip, found 12 hours ago
$119
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Sat, Sep 12 from Greater Rochester Intl. to Tampa Intl., returning Sat, Sep 19, priced at $119 found 12 hours ago
Thu, Aug 27 - Mon, Aug 31
HVN
Tweed - New Haven Regional
TPA
Tampa Intl.
$120 Roundtrip, just found
$120
Roundtrip
just found
Select Avelo Airlines flight, departing Thu, Aug 27 from Tweed - New Haven Regional to Tampa Intl., returning Mon, Aug 31, priced at $120 just found
Fri, Sep 11 - Mon, Sep 14
ROC
Greater Rochester Intl.
LAL
Lakeland Intl. Airport
$121 Roundtrip, found 20 hours ago
$121
Roundtrip
found 20 hours ago
Select Avelo Airlines flight, departing Fri, Sep 11 from Greater Rochester Intl. to Lakeland Intl. Airport, returning Mon, Sep 14, priced at $121 found 20 hours ago
Sat, Sep 12 - Wed, Sep 16
ROC
Greater Rochester Intl.
TPA
Tampa Intl.
$125 Roundtrip, just found
$125
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Sep 12 from Greater Rochester Intl. to Tampa Intl., returning Wed, Sep 16, priced at $125 just found

Winter Haven Flight Information

Traveling To
Winter Haven
Destination Airport IATA Code
TPA
Number of Airlines Serving
Airlines
Breeze Airways, Frontier Airlines, Avelo Airlines
Flight Price
$107
Earliest Departing Flight
Latest Departing Flight

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Winter Haven economy flight packages

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites
2.0-star property

Mar Bay Motel &Suites

Aug 15 - Aug 23

8 night stay

Rochester (ROC) to Tampa (TPA)

Breeze Airways • Non-stop • Coach

Tampa (TPA) to Rochester (ROC)

American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,070, price is now $554 per person
$554
per person
found 17 hours ago
ChartHouse Clearwater Beach Marina Hotel
2.0-star property

ChartHouse Clearwater Beach Marina Hotel

Sep 6 - Sep 11

5 night stay

Hartford (BDL) to Tampa (TPA)

Southwest Airlines • Coach

Tampa (TPA) to Hartford (BDL)

JetBlue Airways • Coach
Save 100% on your flight
Price was $1,002, price is now $602 per person
$602
per person
found 1 day ago
CW Hotel
4.0-star property

CW Hotel

Sep 3 - Sep 8

5 night stay

Hartford (BDL) to Tampa (TPA)

Breeze Airways • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,550, price is now $961 per person
$961
per person
found 1 day ago
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Winter Haven premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Cedar Cove Resort and Cottages
3.0-star property

Cedar Cove Resort and Cottages

9.2/10 Wonderful! (543 reviews)

Sep 4 - Sep 8

4 night stay

Hartford (BDL) to Tampa (TPA)

JetBlue Airways • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,723, price is now $1,081 per person
$1,081
per person
found 6 hours ago
Staff and property was 10/10!!

Reviewed on Jul 13, 2026

Driftwood at Anna Maria Island Inn
3.0-star property

Driftwood at Anna Maria Island Inn

8.6/10 Excellent! (134 reviews)

Sep 4 - Sep 8

4 night stay

Hartford (BDL) to Tampa (TPA)

JetBlue Airways • Non-stop roundtrip • PremiumEconomy
Price was $1,456, price is now $1,163 per person
$1,163
per person
found 6 hours ago
Very clean and quiet, close to all amenities

Reviewed on Jul 12, 2026

Tropic Isle at Anna Maria Island Inn
4.0-star property

Tropic Isle at Anna Maria Island Inn

9/10 Wonderful! (654 reviews)

Sep 4 - Sep 8

4 night stay

Hartford (BDL) to Tampa (TPA)

JetBlue Airways • Non-stop roundtrip • PremiumEconomy
Price was $1,619, price is now $1,312 per person
$1,312
per person
found 6 hours ago
Great location for what we needed

Reviewed on Jul 13, 2026

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Winter Haven business class flight packages

Price found within the past 48 hours. Click for updated prices.
Cedar Cove Resort and Cottages
3.0-star property

Cedar Cove Resort and Cottages

9.2/10 Wonderful! (543 reviews)

Aug 21 - Aug 24

3 night stay

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,320, price is now $960 per person
$960
per person
found 20 hours ago
Staff and property was 10/10!!

Reviewed on Jul 13, 2026

Bali Hai Beachfront Resort and Spa
4.0-star property

Bali Hai Beachfront Resort and Spa

8.6/10 Excellent! (721 reviews)

Aug 21 - Aug 24

3 night stay

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,763, price is now $1,438 per person
$1,438
per person
found 20 hours ago
Accommodations were perfect, even with a late flight.

Reviewed on Jul 12, 2026

Seaside at Anna Maria Island Inn
3.0-star property

Seaside at Anna Maria Island Inn

9.4/10 Exceptional! (115 reviews)

Aug 21 - Aug 24

3 night stay

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $2,504, price is now $2,051 per person
$2,051
per person
found 20 hours ago
Room was definitely not cleaned. Dirty napkins and just generally not wiped down. Solo cups left from the previous guest on the back deck. The views and location were awesome. Also no guarantee in getting a beach front umbrella in front of the rooms. People come early and reserve spots with towels and then maybe they show up maybe not.

Reviewed on Jul 11, 2026

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Winter Haven first class flight packages

Price found within the past 48 hours. Click for updated prices.
CW Hotel
4.0-star property

CW Hotel

No reviews

Aug 18 - Aug 25

7 night stay

New York (JFK) to Tampa (TPA)

Delta • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,182, price is now $1,373 per person
$1,373
per person
found 22 hours ago
We had such a great stay at the CW Resort in Clearwater! The pool area was beautiful and relaxing, the views were amazing, and the entire property was very clean and well maintained. It was the perfect place to unwind and enjoy a Florida getaway. We would definitely stay here again!

Reviewed on Jul 8, 2026

The Marker
2.0-star property

The Marker

6/10 (3 reviews)

Aug 18 - Aug 25

7 night stay

New York (JFK) to Tampa (TPA)

Delta • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,734, price is now $1,941 per person
$1,941
per person
found 22 hours ago

Wyndham Grand Clearwater Beach
4.0-star property

Wyndham Grand Clearwater Beach

9.4/10 Exceptional! (3,447 reviews)

Aug 18 - Aug 25

7 night stay

New York (JFK) to Tampa (TPA)

Delta • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,237, price is now $1,642 per person
$1,642
per person
found 22 hours ago
The hotel was great! The gratuities are added on your checks! Beware because they aren’t very open about that when you go there. We ordered to drinks and our bill was 30.00 and then we also saw a bar fee of almost 3 more dollars! I understand we are at the beach but the 3 wasn’t even on our check I don’t know where it came from. By the way parking is 40.00 a day plus tax!!

Reviewed on Jul 13, 2026

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Winter Haven

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.