I live in Florida, and have since 1994...as well as from 1975 to 1986. We're farther south than Orlando, so we are even hotter in general except in summer, where they can match us.
This year was an outlier. Most wintertimes you can expect to see temperatures with highs from 70 to 82, lows in the mid-60s in Orlando area...that will range from December through late February. Usually 2-3 cold fronts will pass through that will drop temps into the low 50s and lows in the low 40s, with occasional dips to the upper 30s - it's usually for 3-5 nights total, gradually warming each day. This year, we started getting cold fronts in late November, several smaller ones in December, a big dip around New Year's, a few more 4-5 day dips in January, then the giant polar plunge in late January and first week of February, and several more cold dips since, that are likely ending right about now. This was the coldest winter and coldest total winter days since 2010...so very unusual.
Temps generally stay moderate in late February through late March, with highs generally in the low 80s at most, and humidity stays reasonable...the humidity doesn't really start to impact you until the temps climb above 86 or so - then it starts to feel sticky and moist. That can start as early as April, but is definitely locked in by May - and lasts all the way through October. It's possible for a few temperature dips in late October, into the mid-80s, but it's also very possible to still be around 90 and humid all the way into December. Your best times to avoid weather extremes would probably be November and early December, and mid-February to mid-April. January is the most likely month to see some of the colder dips - though again, not like this year which set records throughout the state.
Rainy season is typically summer - so you can get temporary cool downs during rains - but as soon as the rain stops, the heat is still there and all that rain means humidities are close to 100% - so it's like standing in a steam shower after the rain stops.