$41 Cheap flight deals from Boston (BOS) to Howey-in-the-Hills (ORL)

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This Weekend's Flight Deals from Boston to Howey-in-the-Hills

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Jan 25 - Sat, Jan 31
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$96 Roundtrip, found 4 days ago
$96
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sun, Jan 25 from Portsmouth Intl. to Orlando Intl., returning Sat, Jan 31, priced at $96 found 4 days ago
Sun, Jan 25 - Sat, Jan 31
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$96 Roundtrip, found 4 days ago
$96
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sun, Jan 25 from Portsmouth Intl. to Orlando Intl., returning Sat, Jan 31, priced at $96 found 4 days ago
Sun, Jan 25 - Thu, Jan 29
PVD
T.F. Green
MCO
Orlando Intl.
$120 Roundtrip, found 7 hours ago
$120
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Sun, Jan 25 from T.F. Green to Orlando Intl., returning Thu, Jan 29, priced at $120 found 7 hours ago
Sun, Jan 25 - Sat, Jan 31
MHT
Manchester-Boston Regional
MCO
Orlando Intl.
$170 Roundtrip, just found
$170
Roundtrip
just found
Select Breeze Airways flight, departing Sun, Jan 25 from Manchester-Boston Regional to Orlando Intl., returning Sat, Jan 31, priced at $170 just found

Airfares from $41 One Way, $68 Round Trip from Boston to Howey-in-the-Hills

Prices starting at $68 for return flights and $41 for one-way flights to Howey-in-the-Hills were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Feb 10 - Sat, Feb 14
BOS
Boston
MCO
Orlando
$68 Roundtrip, found 8 hours ago
$68
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Tue, Feb 10 from Boston to Orlando, returning Sat, Feb 14, priced at $68 found 8 hours ago
Tue, Feb 24 - Wed, Mar 4
BOS
Boston
MCO
Orlando
$78 Roundtrip, found 10 hours ago
$78
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Tue, Feb 24 from Boston to Orlando, returning Wed, Mar 4, priced at $78 found 10 hours ago
Sat, Apr 4 - Thu, Apr 9
BOS
Boston
MCO
Orlando
$88 Roundtrip, found 2 hours ago
$88
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Apr 4 from Boston to Orlando, returning Thu, Apr 9, priced at $88 found 2 hours ago
Sun, Jan 25 - Sat, Jan 31
PSM
Portsmouth
MCO
Orlando
$96 Roundtrip, found 4 days ago
$96
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sun, Jan 25 from Portsmouth to Orlando, returning Sat, Jan 31, priced at $96 found 4 days ago
Sat, Jan 31 - Wed, Feb 11
MHT
Manchester
MCO
Orlando
$108 Roundtrip, just found
$108
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Jan 31 from Manchester to Orlando, returning Wed, Feb 11, priced at $108 just found

Howey-in-the-Hills economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

8/10 Very Good! (1,367 reviews)

Mar 5 - Mar 9

4 night stay

Boston (BOS) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $638, price is now $314 per person
$314
per person
found 1 day ago
We took our 3 year old nephew here and he had a BLAST! There is so much to do, we didn’t leave for 2 of the 3 days that we stayed. He’s about 42 inches which got him on most of the slides but not all. Keep size in mind when booking for little ones because if they’re under 40in they’re limited to the slides. He was a little bummed that he couldn’t do the pirates plunge (biggest slide) but there were enough distractions that it didn’t matter. Also, the lazy river is great! Just be careful with the big kids, they tend to knock the little ones over or into the wall because they’re just running through it. The water park is an extra fee FYI There’s “ice” skating, swan paddle boats, water park, mini golf, a train trolly, restaurants, arcade, jungle gym, multiple pools. Definitely a good spot if you don’t want to do the parks every day that you’re there! Highly recommend.

Reviewed on Apr 6, 2025

Westgate Towers Resort
3.5-star property

Westgate Towers Resort

8.6/10 Excellent! (1,002 reviews)

Feb 26 - Mar 4

6 night stay

Boston (BOS) to Orlando (MCO)

Delta • Coach

Orlando (MCO) to Boston (BOS)

Spirit Airlines • Coach
Price was $807, price is now $322 per person
$322
per person
found 1 day ago
Great place and very clean. They provide so many amenities

Reviewed on Aug 24, 2025

Westgate Cocoa Beach Resort
4.0-star property

Westgate Cocoa Beach Resort

8.8/10 Excellent! (500 reviews)

Feb 22 - Feb 28

6 night stay

Boston (BOS) to Orlando (MCO)

Spirit Airlines • Coach

Orlando (MCO) to Boston (BOS)

Frontier Airlines • Coach
Price was $2,254, price is now $1,033 per person
$1,033
per person
found 1 day ago
Sue behind the bar was amazing. Hotel is a little dated and could use a new external color scheme. Rooms were modernized and mostly clean (sofa needs vacuumed) We had a great time and made use of all the pool areas and took advantage of happy hour every day. It is a bit of a walk from the main part of the resort to the beach so keep that in mind. Great place for family relaxing

Reviewed on Oct 5, 2025

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Howey-in-the-Hills packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
CoCo Key Hotel and Water Resort 
3.5-star property

CoCo Key Hotel and Water Resort 

8/10 Very Good! (3,666 reviews)

Mar 8 - Mar 13

5 night stay

Boston (BOS) to Orlando (MCO)

Spirit Airlines • PremiumEconomy

Orlando (MCO) to Boston (BOS)

Delta • PremiumEconomy
Price was $677, price is now $477 per person
$477
per person
found 8 hours ago
My wife didn't really care for the place! Pool area was the best part about this place.

Reviewed on Dec 2, 2025

Hyatt Place Orlando/Lake Buena Vista
3.0-star property

Hyatt Place Orlando/Lake Buena Vista

8.4/10 Very Good! (1,397 reviews)

Mar 8 - Mar 13

5 night stay

Boston (BOS) to Orlando (MCO)

Spirit Airlines • PremiumEconomy

Orlando (MCO) to Boston (BOS)

Delta • PremiumEconomy
Price was $771, price is now $573 per person
$573
per person
found 8 hours ago
The breakfast could be more varied.

Reviewed on Dec 4, 2025

DoubleTree by Hilton Orlando Airport
4.0-star property

DoubleTree by Hilton Orlando Airport

8.8/10 Excellent! (2,055 reviews)

Mar 8 - Mar 13

5 night stay

Boston (BOS) to Orlando (MCO)

Spirit Airlines • PremiumEconomy

Orlando (MCO) to Boston (BOS)

Delta • PremiumEconomy
Price was $839, price is now $625 per person
$625
per person
found 8 hours ago
We arrived very late but the stage as very accommodating

Reviewed on Jan 11, 2026

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Howey-in-the-Hills first class flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

8/10 Very Good! (1,367 reviews)

Mar 9 - Mar 13

4 night stay

Boston (BOS) to Orlando (MCO)

American Airlines • FirstClass

Orlando (MCO) to Boston (BOS)

Delta • FirstClass
Price was $1,130, price is now $855 per person
$855
per person
found 1 day ago
We took our 3 year old nephew here and he had a BLAST! There is so much to do, we didn’t leave for 2 of the 3 days that we stayed. He’s about 42 inches which got him on most of the slides but not all. Keep size in mind when booking for little ones because if they’re under 40in they’re limited to the slides. He was a little bummed that he couldn’t do the pirates plunge (biggest slide) but there were enough distractions that it didn’t matter. Also, the lazy river is great! Just be careful with the big kids, they tend to knock the little ones over or into the wall because they’re just running through it. The water park is an extra fee FYI There’s “ice” skating, swan paddle boats, water park, mini golf, a train trolly, restaurants, arcade, jungle gym, multiple pools. Definitely a good spot if you don’t want to do the parks every day that you’re there! Highly recommend.

Reviewed on Apr 6, 2025

Westgate Lakes Resort & Spa Universal Studios Area
4.0-star property

Westgate Lakes Resort & Spa Universal Studios Area

8.2/10 Very Good! (5,482 reviews)

Mar 9 - Mar 13

4 night stay

Boston (BOS) to Orlando (MCO)

American Airlines • FirstClass

Orlando (MCO) to Boston (BOS)

Delta • FirstClass
Price was $1,218, price is now $943 per person
$943
per person
found 1 day ago
It was ok for the price

Reviewed on Sep 27, 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays
4.0-star property

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

9.2/10 Wonderful! (1,001 reviews)

Mar 9 - Mar 13

4 night stay

Boston (BOS) to Orlando (MCO)

American Airlines • FirstClass

Orlando (MCO) to Boston (BOS)

Delta • FirstClass
Price was $1,737, price is now $1,353 per person
$1,353
per person
found 1 day ago
We were very displeased with the cleanliness of our cottage upon arrival. I found multiple hairs on the ground and furniture, so vacuumed Before I even unpacked my suitcase. At the end of the night, our feet were so filthy dirty, we had to wash them before we could get into bed because the floors werent clean. The pool was gross, even had a used band aid in it. The kitchen barely had enough dishes and they left nothing to help with cooking coffee or anything. We've had many vrbo properties in the past, and this was one of the least desirable that we've stayed at.

Reviewed on Oct 7, 2024

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More About Flying To Howey-in-the-Hills from Boston

Route Information for Flights from Boston to Howey-in-the-Hills

Origin Airport IATA Code
BOS
Destination Airport IATA Code
ORL
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Boston to Howey-in-the-Hills

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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.