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Kissimmee

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Kissimmee Flights as Low as $209

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

Breeze Airways
Wed, Aug 5 - Wed, Aug 19
HVN
Tweed - New Haven Regional
MCO
Orlando Intl.
$209 Roundtrip, found 2 days ago
$209
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Aug 5 from Tweed - New Haven Regional to Orlando Intl., returning Wed, Aug 19, priced at $209 found 2 days ago
Avelo Airlines
Fri, Jul 10 - Mon, Jul 13
HVN
Tweed - New Haven Regional
LAL
Lakeland Intl. Airport
$210 Roundtrip, found 3 days ago
$210
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Fri, Jul 10 from Tweed - New Haven Regional to Lakeland Intl. Airport, returning Mon, Jul 13, priced at $210 found 3 days ago
Breeze Airways
Wed, Aug 5 - Wed, Aug 19
HVN
Tweed - New Haven Regional
MCO
Orlando Intl.
$214 Roundtrip, found 2 days ago
$214
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Aug 5 from Tweed - New Haven Regional to Orlando Intl., returning Wed, Aug 19, priced at $214 found 2 days ago
Breeze Airways
Wed, Aug 5 - Wed, Aug 19
HVN
Tweed - New Haven Regional
MCO
Orlando Intl.
$219 Roundtrip, found 2 days ago
$219
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Aug 5 from Tweed - New Haven Regional to Orlando Intl., returning Wed, Aug 19, priced at $219 found 2 days ago
Avelo Airlines
Fri, Jul 10 - Mon, Jul 13
HVN
Tweed - New Haven Regional
LAL
Lakeland Intl. Airport
$220 Roundtrip, found 4 days ago
$220
Roundtrip
found 4 days ago
Select Avelo Airlines flight, departing Fri, Jul 10 from Tweed - New Haven Regional to Lakeland Intl. Airport, returning Mon, Jul 13, priced at $220 found 4 days ago
Breeze Airways
Thu, Aug 6 - Tue, Aug 18
HVN
Tweed - New Haven Regional
MCO
Orlando Intl.
$224 Roundtrip, found 3 days ago
$224
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Aug 6 from Tweed - New Haven Regional to Orlando Intl., returning Tue, Aug 18, priced at $224 found 3 days ago
Avelo Airlines
Fri, Jul 10 - Mon, Jul 13
HVN
Tweed - New Haven Regional
LAL
Lakeland Intl. Airport
$230 Roundtrip, found 5 days ago
$230
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Fri, Jul 10 from Tweed - New Haven Regional to Lakeland Intl. Airport, returning Mon, Jul 13, priced at $230 found 5 days ago
Breeze Airways
Sun, Aug 2 - Thu, Aug 13
HVN
Tweed - New Haven Regional
MCO
Orlando Intl.
$234 Roundtrip, found 3 days ago
$234
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, Aug 2 from Tweed - New Haven Regional to Orlando Intl., returning Thu, Aug 13, priced at $234 found 3 days ago
Breeze Airways
Sun, Aug 2 - Thu, Aug 13
HVN
Tweed - New Haven Regional
MCO
Orlando Intl.
$238 Roundtrip, found 3 days ago
$238
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, Aug 2 from Tweed - New Haven Regional to Orlando Intl., returning Thu, Aug 13, priced at $238 found 3 days ago
Breeze Airways
Sun, Aug 2 - Thu, Aug 13
HVN
Tweed - New Haven Regional
MCO
Orlando Intl.
$244 Roundtrip, found 3 days ago
$244
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, Aug 2 from Tweed - New Haven Regional to Orlando Intl., returning Thu, Aug 13, priced at $244 found 3 days ago
Breeze Airways
Sun, Aug 2 - Thu, Aug 13
HVN
Tweed - New Haven Regional
MCO
Orlando Intl.
$248 Roundtrip, found 3 days ago
$248
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, Aug 2 from Tweed - New Haven Regional to Orlando Intl., returning Thu, Aug 13, priced at $248 found 3 days ago
Breeze Airways
Sun, Aug 2 - Thu, Aug 13
HVN
Tweed - New Haven Regional
MCO
Orlando Intl.
$251 Roundtrip, found 3 days ago
$251
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, Aug 2 from Tweed - New Haven Regional to Orlando Intl., returning Thu, Aug 13, priced at $251 found 3 days ago
American Airlines
Wed, Jun 17 - Tue, Jun 23
ILG
New Castle
MCO
Orlando Intl.
$257 Roundtrip, found 3 days ago
$257
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Jun 17 from New Castle to Orlando Intl., returning Tue, Jun 23, priced at $257 found 3 days ago
Avelo Airlines
Mon, May 18 - Sun, May 24
HVN
Tweed - New Haven Regional
LAL
Lakeland Intl. Airport
$260 Roundtrip, found 6 days ago
$260
Roundtrip
found 6 days ago
Select Avelo Airlines flight, departing Mon, May 18 from Tweed - New Haven Regional to Lakeland Intl. Airport, returning Sun, May 24, priced at $260 found 6 days ago
Avelo Airlines
Sat, Oct 17 - Fri, Oct 30
HVN
Tweed - New Haven Regional
MCO
Orlando Intl.
$277 Roundtrip, found 3 days ago
$277
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Sat, Oct 17 from Tweed - New Haven Regional to Orlando Intl., returning Fri, Oct 30, priced at $277 found 3 days ago
Avelo Airlines
Thu, May 28 - Sun, May 31
ILG
New Castle
LAL
Lakeland Intl. Airport
$340 Roundtrip, found 6 days ago
$340
Roundtrip
found 6 days ago
Select Avelo Airlines flight, departing Thu, May 28 from New Castle to Lakeland Intl. Airport, returning Sun, May 31, priced at $340 found 6 days ago

Cheap Flights to Kissimmee

Fall in love at first flight with your vacation to Kissimmee 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 Kissimmee on Hotwire, and you’ll be up, up, and on a getaway in no time.

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

Frequently Asked Questions About flights to Kissimmee

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Kissimmee 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 Kissimmee?

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 Kissimmee are in August, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Kissimmee?

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 Kissimmee.

What airport is best to fly into Kissimmee?

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

How much are flights to Kissimmee?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Kissimmee on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $209, 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 Kissimmee?

The trick to saving a stack of cash on your flight to Kissimmee? 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 $209 right now, why wait?

Kissimmee Flight Information
Destination airport
Orlando Intl.
Destination airport IATA code
MCO
Roundtrip price
$56

Last Minute Hotel Deals in Kissimmee

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! (4,111 reviews)
Friendly staff, clean room, nice property with a lot to do.

Reviewed on May 12, 2026

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Vacation Village Orlando, Celebration
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3 out of 5
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
Stay at this resort in Kissimmee. Enjoy free breakfast, free WiFi, and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World ...
9.4/10 Exceptional! (3,972 reviews)
We stayed at this resort for 4 days 5 nights. When we first checked in Expedia said we had a perk for the hotel, when we brought it up the front desk said it’s only for gold members and said to ask Expedia. Another issue was the staff was inconsistent with charges of drinks, food, etc. The shower ...

Reviewed on May 12, 2026

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Kompose Boutique Resort at Theme Parks
Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

4 out of 5
8000 Fins Up Circle Kissimmee FL
Book a stay at this spa resort in Kissimmee. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. ...
8.8/10 Excellent! (3,632 reviews)
Only issue I would like to communicate is that the hotel staff at check in. Did not do a very good job explaining amenities pool open/close time water park etc.. They did not explain that there is a shuttle on site that takes you around property. I ubered to IHOP which was a waste of $ there where ...

Reviewed on May 12, 2026

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Margaritaville Resort Orlando with H2O Waterpark
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

4 out of 5
8505 W Irlo Bronson Memorial Hwy Kissimmee FL
Book a stay at this golf resort in Kissimmee. Enjoy free WiFi, free parking, and 7 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
8.8/10 Excellent! (2,895 reviews)
Great resort

Reviewed on May 12, 2026

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Holiday Inn Club Vacations at Orange Lake Resort by IHG
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
4944 W. Irlo Bronson Memorial Highway Kissimmee FL
Stay at this hotel in Kissimmee. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.2/10 Very Good! (5,182 reviews)
The young gentleman that worked the front desk at check in 4pmish was friendly. Some of the other staff, not so much!! The entire property was VERY CLEAN and that matters a lot when traveling! Breakfast was mediocre but well run, and again clean. The pool was nice and the hammocks and dock area were ...

Reviewed on May 12, 2026

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Palazzo Lakeside Hotel
Delta Hotels by Marriott Orlando Celebration

Delta Hotels by Marriott Orlando Celebration

3.5 out of 5
2900 Parkway Blvd Kissimmee FL
Book a stay at this business-friendly hotel in Kissimmee. Enjoy free WiFi, 2 outdoor pools, and 4 restaurants. Our guests praise the pool and the helpful staff ...
8.2/10 Very Good! (2,975 reviews)
Staff was very helpful. Very close to Disney and Universal. Pool is awesome for the whole family. Starbucks inside hotel, ice cream shop and the bar/restaurant all super convenient. Food at restaurant is really good.

Reviewed on May 12, 2026

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Delta Hotels by Marriott Orlando Celebration
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
7700 Westgate Blvd. Kissimmee FL
Book a stay at this family-friendly resort in Kissimmee. Enjoy free parking, 14 outdoor pools, and 2 restaurants. Our guests praise the helpful staff and the ...
8.2/10 Very Good! (1,920 reviews)
They gave away my room and put me in a smaller room. The floor was sticky, sheets were dirty, there were no blankets, the phone didn’t work and the safe didn’t work it took them 3 days and multiple trips to the desk to repair these issues. Staff was friendly, room appeared clean but was not, there ...

Reviewed on May 11, 2026

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Westgate Vacation Villas Resort
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
4736 W Irlo Bronson Hwy Memorial Kissimmee FL
Book a stay at this business-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (3,568 reviews)
Room was beautiful and right at the pool also right downtown and could walk to everything

Reviewed on May 12, 2026

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Seasons Florida Resort
See all 27,367 properties in Kissimmee
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.

Top Hotels With Free Airport Shuttle

Paradise Palms by Home 2U

Paradise Palms by Home 2U

3.5 out of 5
8950 Paradise Palms Blvd Kissimmee FL
Stay at this vacation home in Kissimmee. Enjoy free WiFi, free parking, and private pools. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's ...
Get rates
Paradise Palms by Home 2U
See all 27,367 properties in Kissimmee
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.