$49 Cheap flight deals from Boston (BOS) to Windermere (ORL)

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This Weekend's Flight Deals from Boston to Windermere

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, Mar 1 - Thu, Mar 5
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$159 Roundtrip, found 4 hours ago
$159
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Sun, Mar 1 from Portsmouth Intl. to Orlando Intl., returning Thu, Mar 5, priced at $159 found 4 hours ago
Sun, Mar 1 - Thu, Mar 5
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$159 Roundtrip, found 4 hours ago
$159
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Sun, Mar 1 from Portsmouth Intl. to Orlando Intl., returning Thu, Mar 5, priced at $159 found 4 hours ago
Sat, Feb 28 - Wed, Apr 29
PVD
T.F. Green
MCO
Orlando Intl.
$254 Roundtrip, just found
$254
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Feb 28 from T.F. Green to Orlando Intl., returning Wed, Apr 29, priced at $254 just found
Sun, Mar 1 - Fri, Mar 6
MHT
Manchester-Boston Regional
MCO
Orlando Intl.
$275 Roundtrip, just found
$275
Roundtrip
just found
Select Breeze Airways flight, departing Sun, Mar 1 from Manchester-Boston Regional to Orlando Intl., returning Fri, Mar 6, priced at $275 just found

Airfares from $49 One Way, $98 Round Trip from Boston to Windermere

Prices starting at $98 for return flights and $49 for one-way flights to Windermere 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, Mar 10 - Tue, Mar 24
BOS
Boston
MCO
Orlando
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Mar 10 from Boston to Orlando, returning Tue, Mar 24, priced at $98 found 1 day ago
Sat, May 2 - Wed, May 6
BOS
Boston
MCO
Orlando
$98 Roundtrip, just found
$98
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 2 from Boston to Orlando, returning Wed, May 6, priced at $98 just found
Sat, May 30 - Sat, Jun 6
PSM
Portsmouth
MCO
Orlando
$102 Roundtrip, just found
$102
Roundtrip
just found
Select Breeze Airways flight, departing Sat, May 30 from Portsmouth to Orlando, returning Sat, Jun 6, priced at $102 just found
Sat, Apr 11 - Wed, Apr 15
MHT
Manchester
MCO
Orlando
$103 Roundtrip, found 6 hours ago
$103
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Sat, Apr 11 from Manchester to Orlando, returning Wed, Apr 15, priced at $103 found 6 hours ago
Wed, Aug 26 - Tue, Sep 1
PVD
Providence
MCO
Orlando
$112 Roundtrip, found 6 days ago
$112
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Aug 26 from Providence to Orlando, returning Tue, Sep 1, priced at $112 found 6 days ago

Windermere economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Towers Resort
3.5-star property

Westgate Towers Resort

8.6/10 Excellent! (1,002 reviews)

Apr 2 - Apr 9

7 night stay

Boston (BOS) to Orlando (MCO)

Spirit Airlines • Coach

Orlando (MCO) to Boston (BOS)

Frontier Airlines • Coach
Price was $1,013, price is now $457 per person
$457
per person
found 1 day ago
Great place and very clean. They provide so many amenities

Reviewed on Aug 24, 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)

Apr 2 - Apr 9

7 night stay

Boston (BOS) to Orlando (MCO)

Spirit Airlines • Coach

Orlando (MCO) to Boston (BOS)

Frontier Airlines • Coach
Price was $1,195, price is now $489 per person
$489
per person
found 1 day ago
We had to get 4 room keys for our door to finally work, however staff was kind and helped us as much as they could.

Reviewed on Feb 12, 2026

Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

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

Apr 2 - Apr 9

7 night stay

Boston (BOS) to Orlando (MCO)

Spirit Airlines • Coach

Orlando (MCO) to Boston (BOS)

Frontier Airlines • Coach
Price was $1,098, price is now $469 per person
$469
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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Windermere 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! (1,367 reviews)

Apr 17 - Apr 20

3 night stay

Boston (BOS) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $939, price is now $712 per person
$712
per person
found 10 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

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)

Apr 17 - Apr 20

3 night stay

Boston (BOS) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,390, price is now $1,084 per person
$1,084
per person
found 10 hours 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

Reunion Resort & Golf Club
5.0-star property

Reunion Resort & Golf Club

8.8/10 Excellent! (1,422 reviews)

Apr 17 - Apr 20

3 night stay

Boston (BOS) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,055, price is now $866 per person
$866
per person
found 10 hours ago
I believe the place is outdated. They need to renovate. I also feel like they should make breakfast free and available to all patrons

Reviewed on Oct 15, 2025

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Windermere first class flight packages

Price found within the past 48 hours. Click for updated prices.
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
3.0-star property

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

7.8/10 Good! (188 reviews)

Apr 12 - Apr 18

6 night stay

Boston (BOS) to Orlando (MCO)

Delta • FirstClass

Orlando (MCO) to Boston (BOS)

American Airlines • FirstClass
Price was $1,496, price is now $1,108 per person
$1,108
per person
found 1 day ago
The staff were amazing, the parking for the hotel was horrible.

Reviewed on Jan 3, 2026

Margaritaville Resort Orlando
4.0-star property

Margaritaville Resort Orlando

8.8/10 Excellent! (3,656 reviews)

Apr 12 - Apr 18

6 night stay

Boston (BOS) to Orlando (MCO)

Delta • FirstClass

Orlando (MCO) to Boston (BOS)

American Airlines • FirstClass
Price was $1,648, price is now $1,411 per person
$1,411
per person
found 1 day ago
Room was out of this hemisphere. I will keep coming back every time we do Disney! Thanks for the upgrade!

Reviewed on Dec 24, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
4.0-star property

DoubleTree by Hilton at the Entrance to Universal Orlando

8.4/10 Very Good! (6,833 reviews)

Apr 12 - Apr 18

6 night stay

Boston (BOS) to Orlando (MCO)

Delta • FirstClass

Orlando (MCO) to Boston (BOS)

American Airlines • FirstClass
Price was $1,621, price is now $1,413 per person
$1,413
per person
found 1 day ago
Everything was great. The staff were super nice and accommodating. The food was super fresh. The plus was our room had a window facing universal so we saw the firework and drone show every night we were there.

Reviewed on Dec 29, 2025

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More About Flying To Windermere from Boston

Route Information for Flights from Boston to Windermere

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

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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.