As others have stated, $300/month puts you somewhere between $15k and $17k. I'd try to find a gently-used late-model Pathfinder or 4Runner or maybe even an Xterra. But then I go hiking/camping alot so it would actually see more than city streets 🙂
Edit:
I very much agree with BoogieMan, though. Unless you're just trying to impress your friends, you're approaching this decision wrong. First decide what you're looking for (sedan, coupe, truck/SUV?). Are you willing to buy a late-model used vehicle? Then weed out the models that are out of your budget.
If you go car shopping with the mindset that you're going to $300/month, that's probably what you're going to walk away with.