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Windermere

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Windermere Flights as Low as $66

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

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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 April, 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 $66, 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 $66 right now, why wait?

Windermere Flight Information
Destination airport
Orlando Sanford Intl.
Destination airport IATA code
SFB
Roundtrip price
$339

Last Minute Hotel Deals in Windermere

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
Book a stay at this family-friendly 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! (4,646 reviews)
Nice room, no breakfast on weekdays! Marketplace ran out of pepperoni pizzas. Shuttle service was very good. Reserved parking fee on credit card even though I have a car? (Removed at checkout)

Reviewed on Feb 19, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
8/10 Very Good! (9,067 reviews)
Bathroom -shower had soap residue in drain and floors weren’t too clean. Floors weren’t clean

Reviewed on Feb 19, 2026

The Grove Resort & Water Park Orlando
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
Book a stay at this 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! (6,894 reviews)
Room has a mold smell and smoke smell

Reviewed on Feb 19, 2026

DoubleTree by Hilton at the Entrance to Universal Orlando
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way Orlando FL
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (6,372 reviews)
food was terrible, had to buy floaties for lazy river which is so worthless since we flew in and can't really take it back.

Reviewed on Feb 19, 2026

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
Book a stay at this family-friendly resort in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
7.6/10 Good! (6,566 reviews)
Despite Expedia showing a “what you see is what you pay” price be prepared to pay an extra 100+ for parking and resort fees. The fact that they have the parking listed as an “optional” fee despite it being mandatory is absolutely scummy. Also, pictures are misleading in showing that the stay would ...

Reviewed on Feb 19, 2026

DoubleTree by Hilton Hotel Orlando at SeaWorld
Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

3 out of 5
2975 Arabian Nights Blvd Kissimmee FL
Book a stay at this family-friendly condo in Kissimmee. Enjoy free WiFi, 7 outdoor pools, and 7 hot tubs. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (3,405 reviews)
The room was clean and well equipped. The location and grounds are perfect. The check-in was a little painful and we initially were given a room that was occupied. The second room was good.

Reviewed on Feb 20, 2026

Vacation Village Orlando, Celebration
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista Orlando FL
Book a stay at this 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. ...
9/10 Wonderful! (3,911 reviews)
Everything was amazing, rooms were large and clean, staff was attentive and the location was perfect!!

Reviewed on Feb 18, 2026

Marriott's Grande Vista
Sonesta Essential Orlando Airport

Sonesta Essential Orlando Airport

3 out of 5
8101 Aircenter Ct Orlando FL
Stay at this hotel in Orlando. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8/10 Very Good! (600 reviews)
We had issues with the TV in the room. We made several attempts to get it working, then took the remote to the front desk thinking that it needed batteries. The front desk clerk gave us a remote that was not compatible with the tv. Finally after several trips he came down and got the tv and remote ...

Reviewed on Feb 20, 2026

Sonesta Essential Orlando Airport
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.