RIGHT next door to Windsor Hills is Mystic Dunes, the #2 rated course in Orlando. (Bay Hill is rated #1, but it's a country club, have to be a member to play there). I just played there in Jan, you do have to take a cart I believe, and it was roughly $140 for a round.
This does include free range balls, you can go to the range beforehand and hit as many balls as you like, very nice clubhouse / range (all grass tees).
The only part of Mystic Dunes I didn't like....they were having timeshare people tour all over the resort, and they were walking around the 17th and 18th green talking VERY loudly while we were putting, I actually called the ranger to complain about it, when you pay that much for golf it's unacceptable.
You can probably walk on, but I would always suggest a tee time. Depending on his handicap, that sort of thing, the starters will generally try and put you with someone who's comparable to you in terms of skill.
I would also strongly suggest he gets out and trys one of Disney's 4 championship courses. We played Osprey Ridge in Jan as well, and like all things Disney, it's simply top notch! (Definitely need a tee time / reservation though).
Also close by is Champion's Gate...and Falcon's Fire isn't too far away either. All of these places are going to run you $150 for a round with a cart, or in that neighborhood. I'm sure there are less expensive courses in the area, but these are the ones I'm most familiar with, and I've played MD and OR.
I got lost over by Champion's Gate once and then realized it's only 5 minutes away from Windsor Hills too, LOL, so I know it's pretty close by!
Any pro will tell you though, if you're playing alone, it's best to call the local starter, tell him what you're interest is, and a high end club (all of these are VERY high end golf courses, some of the best in the US), will do it's absolute best to accomodate you, hook you up with someone at your level, that sort of thing, but they need to know what you're looking for in advance. (I take lessons here in Chicago over the winter indoors).
For instance, when I go play with my DW who is just learning, we let the starters know about this, that we're looking for a nice slow paced game, we start later in the day so as not to hold up people who are very good and want to play fast, and they might then also pair us up with someone at the same level. When I play at the same course with a buddy who's a handicap 8, he gets very frustrated when we get held up or waiting on anyone in front of us who can't play at a very fast pace.
Hope this helps some, if he's looking for less expensive places let me know, I'll call some of my "local" golfer friends down there and find out what places they recommend, I'm supposed to play with them next week there actually!
Oh...don't forget to remind DH that Windsor Hills just opened up a high end chipping and putting practice facility in November!
We've had several guests now tell us their DH was out there every morning practicing putting!