Winter Garden is great--a walkable downtown with a lot of places to try. I recommend Urban Flats and the Italian place near Pilars (blanking on the name), but I've heard good things about other places around there as well. If you're a beer drinker, stop by Crooked Can Brewing as well. Actually, if you go there, the pizza and mac & cheese places in the same food hall are terrific. 20 minutes north of Disney on the 429.
Lot of good choices in Celebration, and another downtown you can walk around and just soak up the atmosphere for the evening. I'm a big fan of the Columbia, a small family-owned chain (there's only 5 of them) specializing in Spanish/Cuban food and the Celebration Town Tavern, which does basic New England bar food really well with a great staff. Thai Tani (Thai food, natch) also good, as is Upper Crust if you just want a pizza to go. Literally adjacent to WDW property, off World Drive.
Jerusalem is a hidden gem at 535/192 in the heart of the tourist area. Middle Eastern food, very affordable. A few doors down, the Red Dog Pub is a dive bar but they have cheap booze, a limited menu featuring New Orleans food alongside the usual bar fare, and great live music most nights. 5 minutes from the Mouse.
All of the above are various degrees of reasonably priced. Sand Lake Road and I-Drive have a lot of places, but most command theme park prices. Graffiti Junktion (technically on Turkey Lake Rd. near Universal) does good burgers fairly cheap; The Whiskey, on Sand Lake Rd., makes even better burgers, but it can get pricey. They get a lot of cool local bands there which makes it fun.
It's a Darden chain, but Bahama Breeze always "feels" like Florida to me, is affordable compared to the Mouse. Best one for atmosphere is on I-Drive, but menu is solid at all of them. Cafe Tu Tu Tango, also on I-Drive, is worth a look, as well, in terms of uniqueness, tho it's small plates so the bill adds up quickly.