Hi Catmoney:
We love the Cottages at Camp Creek, about 1/2 mile west of Alys Beach, 1 mile west of Rosemary Beach. They're charming 3 bedroom/2 bath cottages with two car parking and a large porch. There's a very large pool for a not-to-big community (about 20 small cottages and 8 larger ones - don't quote me, I'm writing too early in the morning to count) that's quiet with a quiet beach across the stree (about a 4-5 minute walk). We bought our first cottage at the Cottages at Camp Creek in 2003 and then liked it so much we bought the one next door in 2004. They have dropped in value since then, but that didn't affect us because we plan to keep them for decades. I know some people have gotten what looks to me like a very good deal in the past year, but (as a few people note on the board) you never know where the bottom of the market is (whether it's coming or has passed) and that also depends on the community. You can check with a realtor, but I think prices at the Cottages at Camp Creek may have started increasing again (based on what I've been told people paid for their cottages over the past year).
As was already noted on this board, don't assume rental income will cover all of your expenses, even in a year when there are no special events such as hurricanes (I think 2005 was the last one that affected us directly) and oil spills. I do think the rentals on the cottages will pay all the bills once the mortgage are paid, but I don't know that for sure. At this point, our cottages rent for 2-3 months each winter (we have return snowbird guests), a few fall rentals (not many), full in the summer (end of May - first week in August), and spring is better than fall, but spotty.
And there's always maintenance (which is why I like a one story place - I can do much of the maintenance myself - e.g., paint the window and door trim, power wash the cottages, etc.). I don't always do it myself because I don't have time, but I can when I want to.
I hope this helps with some of your planning. Just PM me if you have more questions.
Best,
Paula