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Windermere

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Windermere Flights as Low as $69

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

Frontier Airlines
Sat, Sep 6 - Thu, Sep 18
CLT
Charlotte-Douglas Intl.
MCO
Orlando Intl.
$69 Roundtrip, found 6 hours ago
$69
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sat, Sep 6 from Charlotte-Douglas Intl. to Orlando Intl., returning Thu, Sep 18, priced at $69 found 6 hours ago
Frontier Airlines
Fri, Sep 12 - Thu, Sep 18
CLT
Charlotte-Douglas Intl.
MCO
Orlando Intl.
$72 Roundtrip, found 23 hours ago
$72
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Fri, Sep 12 from Charlotte-Douglas Intl. to Orlando Intl., returning Thu, Sep 18, priced at $72 found 23 hours ago
Frontier Airlines
Sun, Sep 7 - Mon, Sep 22
CLT
Charlotte-Douglas Intl.
MCO
Orlando Intl.
$73 Roundtrip, found 6 hours ago
$73
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sun, Sep 7 from Charlotte-Douglas Intl. to Orlando Intl., returning Mon, Sep 22, priced at $73 found 6 hours ago
Frontier Airlines
Sat, Sep 6 - Sat, Sep 20
CLT
Charlotte-Douglas Intl.
MCO
Orlando Intl.
$78 Roundtrip, just found
$78
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Sep 6 from Charlotte-Douglas Intl. to Orlando Intl., returning Sat, Sep 20, priced at $78 just found
Frontier Airlines
Fri, Sep 12 - Tue, Sep 16
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$89 Roundtrip, found 14 hours ago
$89
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Fri, Sep 12 from Philadelphia Intl. to Orlando Intl., returning Tue, Sep 16, priced at $89 found 14 hours ago
Spirit Airlines
Sat, Aug 30 - Thu, Sep 4
BDL
Bradley Intl.
MCO
Orlando Intl.
$91 Roundtrip, just found
$91
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Aug 30 from Bradley Intl. to Orlando Intl., returning Thu, Sep 4, priced at $91 just found
Breeze Airways
Sat, Aug 30 - Thu, Sep 4
BDL
Bradley Intl.
MCO
Orlando Intl.
$92 Roundtrip, just found
$92
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Aug 30 from Bradley Intl. to Orlando Intl., returning Thu, Sep 4, priced at $92 just found
Frontier Airlines
Sat, Aug 30 - Fri, Sep 5
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$97 Roundtrip, found 1 hour ago
$97
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Aug 30 from John F. Kennedy Intl. to Orlando Intl., returning Fri, Sep 5, priced at $97 found 1 hour ago
Spirit Airlines
Wed, Sep 3 - Wed, Sep 10
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$99 Roundtrip, found 2 days ago
$99
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Sep 3 from Philadelphia Intl. to Orlando Intl., returning Wed, Sep 10, priced at $99 found 2 days ago
Breeze Airways
Wed, Oct 22 - Sat, Oct 25
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$107 Roundtrip, found 2 days ago
$107
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Oct 22 from Portsmouth Intl. to Orlando Intl., returning Sat, Oct 25, priced at $107 found 2 days ago
Spirit Airlines
Mon, Oct 20 - Thu, Oct 23
BOS
Logan Intl.
MCO
Orlando Intl.
$110 Roundtrip, found 20 hours ago
$110
Roundtrip
found 20 hours ago
Select Spirit Airlines flight, departing Mon, Oct 20 from Logan Intl. to Orlando Intl., returning Thu, Oct 23, priced at $110 found 20 hours ago
Frontier Airlines
Thu, Sep 4 - Fri, Sep 5
TTN
Mercer
MCO
Orlando Intl.
$129 Roundtrip, found 6 hours ago
$129
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Thu, Sep 4 from Mercer to Orlando Intl., returning Fri, Sep 5, priced at $129 found 6 hours ago
JetBlue Airways
Tue, Nov 11 - Tue, Nov 18
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$137 Roundtrip, just found
$137
Roundtrip
just found
Select JetBlue Airways flight, departing Tue, Nov 11 from John F. Kennedy Intl. to Orlando Intl., returning Tue, Nov 18, priced at $137 just found
Delta
Tue, Dec 2 - Tue, Dec 9
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$137 Roundtrip, found 14 hours ago
$137
Roundtrip
found 14 hours ago
Select Delta flight, departing Tue, Dec 2 from John F. Kennedy Intl. to Orlando Intl., returning Tue, Dec 9, priced at $137 found 14 hours ago
American Airlines
Tue, Nov 11 - Tue, Nov 18
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$159 Roundtrip, just found
$159
Roundtrip
just found
Select American Airlines flight, departing Tue, Nov 11 from John F. Kennedy Intl. to Orlando Intl., returning Tue, Nov 18, priced at $159 just found
United
Tue, Sep 9 - Sat, Sep 13
BOS
Logan Intl.
MCO
Orlando Intl.
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 9 from Logan Intl. to Orlando Intl., returning Sat, Sep 13, priced at $200 found 1 day ago

Cheap Flights to Windermere

Fall in love at first flight with your vacation to Windermere by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Windermere on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Windermere, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Windermere

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Windermere with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the ORL airport.

What is the cheapest month to fly to Windermere?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Windermere are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Windermere?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Windermere.

What airport is best to fly into Windermere?

When you’re planning your trip to Windermere, convenience is the name of the game. Luckily, Windermere Orlando Intl. Airport is nearby so you can deplane and get going on checking off everything on your Windermere must-do list.

How much are flights to Windermere?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Windermere on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $69, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Windermere?

The trick to saving a stack of cash on your flight to Windermere? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $69 right now, why wait?

Windermere Flight Information
Destination airport
Orlando Intl.
Destination airport IATA code
MCO
Roundtrip price
$69

Last Minute Hotel Deals in Windermere

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd, Orlando, FL
Stay at this 4-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.4/10 Very Good! (6,536 reviews)
"I liked the breakfast bar !"

Reviewed on Aug 17, 2025

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DoubleTree by Hilton at the Entrance to Universal Orlando
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista, Orlando, FL
Stay at this 4-star spa hotel in Orlando. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. ...
8.8/10 Excellent! (2,856 reviews)
"Family friendly. Daily pool side activities for guest, pool side movie was my fav. Friendly staff all throughout the property. They supply clean towels at the pool which is nice because most hotels you have to take them from your"

Reviewed on Aug 15, 2025

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Marriott's Grande Vista
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way, Orlando, FL
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
8.8/10 Excellent! (5,128 reviews)
"Great vacation spot if traveling with kids"

Reviewed on Aug 16, 2025

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Universal's Cabana Bay Beach Resort
DoubleTree by Hilton Hotel Orlando at SeaWorld

DoubleTree by Hilton Hotel Orlando at SeaWorld

4 out of 5
10100 International Drive, Orlando, FL
Stay at this 4-star family-friendly resort in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
7.4/10 Good! (6,065 reviews)
"Good"

Reviewed on Aug 15, 2025

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DoubleTree by Hilton Hotel Orlando at SeaWorld
Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

3 out of 5
341 Flagler Ave, Winter Garden, FL
Stay at this 3-star business-friendly hotel in Winter Garden. Enjoy free breakfast, a free theme park shuttle, and a 24-hour fitness center. Our guests praise ...
9.2/10 Wonderful! (4,453 reviews)
"very good"

Reviewed on Aug 15, 2025

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Home2 Suites by Hilton Orlando at Flamingo Crossings
Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

3.5 out of 5
3011 Maingate Ln, Kissimmee, FL
Stay at this 3.5-star family-friendly hotel in Kissimmee. Enjoy free parking, 2 outdoor pools, and breakfast (surcharge). Our guests praise the helpful staff ...
8.4/10 Very Good! (437 reviews)
"Nice pool and comfortable bed. Great location for Disney"

Reviewed on Aug 14, 2025

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Holiday Inn Resort Kissimmee by the Parks by IHG
CoCo Key Hotel and Water Resort 

CoCo Key Hotel and Water Resort 

3.5 out of 5
7400 International Dr, Orlando, FL
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy 3 outdoor pools, 4 restaurants, and 2 poolside bars. Our guests praise the pool and the helpful ...
7.8/10 Good! (3,493 reviews)
"All"

Reviewed on Aug 15, 2025

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CoCo Key Hotel and Water Resort 
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr, Orlando, FL
Stay at this 4-star eco-certified hotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in ...
9.2/10 Wonderful! (3,364 reviews)
"The prop3was beautiful staff was welcoming and we had a great time! Cant wait to go back."

Reviewed on Aug 15, 2025

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Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
See all 52,295 properties in Windermere
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.