where in Orlando area are you? co-incidentally a guy name Ron just barely started the meetup grouphttp://www.meetup.com/Seminole-County-Boardgamers/
which he's been scheduling game nights in Lake Mary. The largest (w/over 600 members) board gaming meetup for Orlando metro I believe is:http://www.meetup.com/OrlandoGameNight/
I've been hosting fairly regularly on Saturday's (including today) at my house in Longwood focusing specifically on Euro/Strategy's (vs. party/trivia/monopoly). Another guy here in Longwood hosts once a month on Saturday and opens it to all types of games, as well as other folks hosting.
I haven't tried it out yet but then there is also:http://www.meetup.com/SciFiCityGames/
which has Tuesday and Thursday game nights.
I've also heard positive things abouthttp://www.facebook.com/AmorousArmadilloGameShoppe
but it's not clear they have a game night right now as I had heard they closed, but checking they simply moved (from Oveido to not far from CoolStuff's Winter Park store).
And as Jesse said CoolStuff Maitland store (on 17-92 close to SR436) has "board game night" on Wednesday's... however your mileage may vary as while it's billed as board game night, just like every other night the place is over run by Magic the Gathering players and the background noise level is hard for me. Also no one really "runs" the game night and as would be expected the gamers there have formed cliques, and I think I went to cool stuff (in Winter Park before Maitland opened) 3 or 4 times and I never was able to get in a more meaty euro/strategy game due to the cliquish nature... but hopefully if you go ymmv