If you're staring at a screen right now trying to figure out what to pack for your trip to Old Town or Disney, I get it. Central Florida in January is a bit of a wildcard. One minute you're basking in a glorious 75°F afternoon, and the next, a cold front sweeps down from the Panhandle and you’re shivering in line for a Dole Whip. People think Florida is just "hot" all the time. Honestly? That is the quickest way to end up miserable and buying a $60 overpriced hoodie at a gift shop.
When looking at the weather forecast Kissimmee Florida 15 days out, you have to look past the icons. A little "cloudy" icon doesn't tell the whole story.
Currently, as we move through the back half of January 2026, Kissimmee is settling into its classic winter rhythm. The data from the Orlando International Airport stations shows a month that started significantly warmer than last year—nearly 14 degrees warmer on average—but the next two weeks are bringing us back to reality. We are looking at daytime highs that hover right around 70°F (21°C), which sounds perfect, until you realize the sun sets before 6:00 PM and the temperature drops like a stone.
The Reality of the Weather Forecast Kissimmee Florida 15 Days Out
Looking at the upcoming two-week stretch, the numbers are fairly consistent but deceptive. You’ll see highs of 70°F to 74°F for the most part. Overnight? It's hitting 52°F or even 49°F on the clearer nights.
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Humidity is sitting at a comfortable 72%, which is low for Florida. This is the "dry season," but that doesn't mean "no rain." The historical probability of rain increases as we head toward February. Right now, there’s about a 16% to 22% chance of a wet day. It’s rarely a washout, though. It’s usually those quick, gray "sprinkles" that pass through in an hour and leave the air feeling crisp.
Why the "Daily High" is a Lie
Most travelers look at the high of 73°F and pack shorts. Big mistake. In Kissimmee, you aren't living in the "high" for very long. The peak temperature usually hits around 3:00 PM. By the time you're heading to dinner at 6:30 PM, the thermometer is already sliding into the 50s. If you’re standing in an outdoor queue or walking around Celebration, that 20-degree swing feels massive.
Wind and Cloud Cover Factors
January is actually the windiest month for this region. We’re seeing average wind speeds of about 14 mph, with gusts reaching higher when fronts move through. 14 mph at 72 degrees feels like a nice breeze; 14 mph at 55 degrees feels like a piercing chill.
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Cloud cover is also hovering around 41%. It’s not the gloom of London, but it’s enough to block the warming effect of the sun for several hours a day. April is actually the sunniest month here, so don't expect wall-to-wall blue skies every single day of your 15-day window.
How to Actually Prepare for Kissimmee in Late January
Since the weather forecast Kissimmee Florida 15 days out shows this "yo-yo" effect, your suitcase needs to be strategic. Forget the heavy winter parka, but also don't rely on just tees.
- The Shell Layer: Bring a light windbreaker or a denim jacket. This handles the 14 mph winds without being bulky.
- The Morning Strategy: If you're hitting the parks at 7:30 AM, it's going to be around 53°F. Wear layers you can peel off by noon.
- Footwear Nuance: It’s dry enough for sneakers, but the grass stays damp with dew until late morning. Mesh shoes might get your socks soggy if you're walking through parks early.
Historical Perspective vs. 2026 Trends
Looking at the data from the last 30 years (1992–2021), January is officially the coldest month in Kissimmee. The record lows can occasionally dip into the 30s, though we aren't seeing that in the current 15-day outlook. Most of the "comfortable" days in this region happen between January and April, which is why the crowds are often so thick right now. People are fleeing the northern snow for our "mildly cool" 70-degree days.
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What Most People Get Wrong About Florida "Rain"
In the summer, rain is a clockwork thunderstorm at 4:00 PM. In January, rain is usually tied to a cold front. This means if it rains today, tomorrow is probably going to be 10 degrees colder and much windier. Check the barometric pressure if you’re a weather nerd—29.8 to 30.1 "Hg is the current range. When it drops, the front is coming.
Actionable Tips for Your 15-Day Window
- Monitor the "Dew Point," not just Humidity. If the dew point is below 55°F, it will feel chilly the moment the sun goes down.
- Plan Indoor Evenings. If the forecast shows a low of 50°F, maybe do your outdoor walking during the day and save the indoor shows or shopping for after 6:00 PM.
- Sunscreen is still mandatory. Even with 41% cloud cover and 70-degree air, the UV index is sitting at a 5 (Moderate). You will still burn while waiting for the ferry.
- Check the "Feels Like" Temp. In the shade with a 15 mph wind, 70°F feels like 64°F.
The next 15 days in Kissimmee are looking like classic "Chamber of Commerce" weather—mostly pleasant, slightly brisk, and perfectly dry for outdoor activities. Just don't let the "Florida" label trick you into leaving your jacket at home.
To make the most of this window, download a high-resolution radar app to track the small sprinkle cells that tend to pop up near the Kissimmee chain of lakes during these breezy January afternoons.