$44 Cheap flight deals from Boston (BOS) to Winter Garden (ORL)

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This Weekend's Flight Deals from Boston to Winter Garden

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.

Sat, Jul 26 - Sat, Aug 2
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$116 Roundtrip, found 5 days ago
$116
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Jul 26 from Portsmouth Intl. to Orlando Intl., returning Sat, Aug 2, priced at $116 found 5 days ago
Sat, Jul 26 - Sat, Aug 2
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$116 Roundtrip, found 5 days ago
$116
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Jul 26 from Portsmouth Intl. to Orlando Intl., returning Sat, Aug 2, priced at $116 found 5 days ago
Sat, Jul 26 - Sat, Aug 2
MHT
Manchester-Boston Regional
MCO
Orlando Intl.
$154 Roundtrip, found 2 hours ago
$154
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Sat, Jul 26 from Manchester-Boston Regional to Orlando Intl., returning Sat, Aug 2, priced at $154 found 2 hours ago
Sun, Jul 27 - Thu, Jul 31
PVD
T.F. Green
MCO
Orlando Intl.
$189 Roundtrip, found 3 days ago
$189
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, Jul 27 from T.F. Green to Orlando Intl., returning Thu, Jul 31, priced at $189 found 3 days ago

Airfares from $44 One Way, $87 Round Trip from Boston to Winter Garden

Prices starting at $87 for return flights and $44 for one-way flights to Winter Garden 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, Aug 12 - Sat, Aug 16
BOS
Boston
MCO
Orlando
$87 Roundtrip, found 10 hours ago
$87
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Tue, Aug 12 from Boston to Orlando, returning Sat, Aug 16, priced at $87 found 10 hours ago
Sat, Oct 4 - Sat, Oct 11
PSM
Portsmouth
MCO
Orlando
$102 Roundtrip, found 2 hours ago
$102
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Sat, Oct 4 from Portsmouth to Orlando, returning Sat, Oct 11, priced at $102 found 2 hours ago
Wed, Oct 1 - Sat, Oct 4
MHT
Manchester
MCO
Orlando
$102 Roundtrip, found 8 hours ago
$102
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Wed, Oct 1 from Manchester to Orlando, returning Sat, Oct 4, priced at $102 found 8 hours ago
Thu, Sep 25 - Wed, Oct 1
PVD
Providence
MCO
Orlando
$102 Roundtrip, found 3 hours ago
$102
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Thu, Sep 25 from Providence to Orlando, returning Wed, Oct 1, priced at $102 found 3 hours ago
Fri, Aug 15 - Mon, Aug 18
BOS
Boston
MCO
Orlando
$105 Roundtrip, found 8 hours ago
$105
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Fri, Aug 15 from Boston to Orlando, returning Mon, Aug 18, priced at $105 found 8 hours ago

Winter Garden economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Lakes Resort & Spa Universal Studios Area
4.0-star property

Westgate Lakes Resort & Spa Universal Studios Area

8.2/10 Very Good! (5,097 reviews)

Sep 19 - Sep 22

3 night stay

Boston (BOS) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Pros: Clean, beautiful grounds. There are pools throughout the property, and food/store options available onsite. Beds were comfortable. Nice patios. Able to get bus to Universal for free. Cons: Check in was awful. Took close to 1 hour. There is a shuttle that can take you from your building to the front as it's a long walk. However, we mostly had to walk because the shuttle was either parked up front or MIA. The property and rooms are dated. Plugs/outlets in the room were few and we had two just not even work in our room. The waterpark was fine, but requires additional paid entry for non-members. Pools on property are just open swimming..no attendants.

Reviewed on Jun 23, 2025

Westgate Blue Tree Resort in Lake Buena Vista
3.5-star property

Westgate Blue Tree Resort in Lake Buena Vista

8.4/10 Very Good! (995 reviews)

Aug 28 - Sep 2

5 night stay

Boston (BOS) to Orlando (MCO)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Originally got a one bedroom villa and got a free upgrade to a two bedroom which was perfect. The villa was super clean, easy access, washer/dryer, kitchen fully stored with pots, pans, utensils, cups, and plates. They had enough towels for our entire stay, and even had beach towels as well. They had everything that you needed. I didn’t need to call the front desk for anything my entire stay. I loved that place and the size of the villa was perfect for the two of us and maybe more. Definitely will come back if I’m ever back in Orlando.

Reviewed on Jun 11, 2025

Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

8/10 Very Good! (1,277 reviews)

Aug 30 - Sep 4

5 night stay

Boston (BOS) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
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

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Winter Garden packages with premium economy flights

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! (1,277 reviews)

Sep 13 - Sep 17

4 night stay

Boston (BOS) to Orlando (MCO)

Delta • Roundtrip • PremiumEconomy
per person
found 9 hours 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 Palace Hotel / Universal / I-Drive
4.0-star property

Westgate Palace Hotel / Universal / I-Drive

8.6/10 Excellent! (1,006 reviews)

Sep 13 - Sep 17

4 night stay

Boston (BOS) to Orlando (MCO)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 9 hours ago
Only thing that we complained was bed sheets were dirty and floor in one of the room full of hair.

Reviewed on Jul 3, 2025

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

Westgate Lakes Resort & Spa Universal Studios Area

8.2/10 Very Good! (5,097 reviews)

Sep 13 - Sep 17

4 night stay

Boston (BOS) to Orlando (MCO)

Delta • Roundtrip • PremiumEconomy
per person
found 9 hours ago
Pros: Clean, beautiful grounds. There are pools throughout the property, and food/store options available onsite. Beds were comfortable. Nice patios. Able to get bus to Universal for free. Cons: Check in was awful. Took close to 1 hour. There is a shuttle that can take you from your building to the front as it's a long walk. However, we mostly had to walk because the shuttle was either parked up front or MIA. The property and rooms are dated. Plugs/outlets in the room were few and we had two just not even work in our room. The waterpark was fine, but requires additional paid entry for non-members. Pools on property are just open swimming..no attendants.

Reviewed on Jun 23, 2025

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Winter Garden first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Resort on Cocoa Beach
3.5-star property

The Resort on Cocoa Beach

9.4/10 Exceptional! (564 reviews)

Sep 12 - Sep 15

3 night stay

Boston (BOS) to Orlando (MCO)

Delta • Roundtrip • FirstClass
per person
found 1 day ago
Our room was perfect for the 5 of us. The room smelled very strongly of mold/mildew. That was our biggest complaint. Otherwise parking was good. The pool and hot tub were great and all the activities planned were super fun. The walk to the beach is quick close and safe feeling. The beach was clean and so nice to relax. Place on the hotel side to rent chairs umbrellas boogie boards and surf boards for minimal prices. You don't need to pack your beach towel they are there and free of charge. We came down for spring break and as a single mom with four girls coming in it was a wonderful spot. It was safe. We joked that it was kind of the geriatric form of spring break, but it was wonderful. We hope to return again.

Reviewed on Mar 23, 2025

Westgate Cocoa Beach Resort
4.0-star property

Westgate Cocoa Beach Resort

8.8/10 Excellent! (478 reviews)

Sep 12 - Sep 15

3 night stay

Boston (BOS) to Orlando (MCO)

Delta • Roundtrip • FirstClass
per person
found 1 day ago
Our room was beautiful, very clean and equipped with everything we could need. Unfortunately the pool was out of commission along with the hot tub but wasn’t communicated after booking. There isn’t much to do at the hotel if you catch a rainy day like we did

Reviewed on Jan 25, 2022

Harbor Island Beach Club by Villatel
2.0-star property

Harbor Island Beach Club by Villatel

9.4/10 Exceptional! (3 reviews)

Sep 12 - Sep 15

3 night stay

Boston (BOS) to Orlando (MCO)

Delta • Roundtrip • FirstClass
per person
found 1 day ago
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More About Flying To Winter Garden from Boston

Route Information for Flights from Boston to Winter Garden

Origin Airport IATA Code
BOS
Destination Airport IATA Code
ORL
Distance
1121 mi
Direct Flight Airlines
KLM, Qatar Airways, JAL, Icelandair, Azul, Aer Lingus, Air France, Delta Air Lines, Aeromexico, El Al, Etihad Airways, JetBlue, LATAM Airlines, SAS, Hawaiian Airlines, Korean Air, TAP Air Portugal, Virgin Atlantic, Spirit Airlines, British Airways
Earliest Flight Arrival
1:39PM UTC
Latest Flight Arrival
3:59AM UTC

Boston to Winter Garden

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Boston to Winter Garden flights at discounted rates

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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.