The best times depend on what you want. If you have kids and want them to find other kids, then the official spring and summer breaks are perfect (You would want to find a place that doesn't require much driving and has everything your family needs, though, because traffic can be very busy and not worth the hassle of trying to get around much). If you want to be in the area when it's very quiet, then the August-Memorial day period is best. If cost matters, then November 1 through end of February would be the least expensive - very low rental rates compared to the rest of Florida because it's off-season, yet great weather (especially if you're a northerner and escaping the cold weather), great restaurants (most are open when we're here), quiet, great sunsets (as always, no traffic problems. August is our favorite time to go with kids because because it is quiet and the pool and ocean are still warm. October has beautiful monarch butterflies migrating south through SoWal. That week between Christmas and New years is fun because the Seaside concert on NY Eve is great (I don't know if there are concerts at Rosemary and Alys Beach as well - if so, we'd probably try Alys for a chance this year). Watching the fireworks along the shore on NY Eve at midnight is beautiful. Winter has a lot of events - seeing red wine festival, seaside garage sale, and more. Just check the event calendar here on SoWal.com to see what some of the events are. Visiting in May before summer break starts around Memorial Day is like visiting in the summer except it's quiet and the rental rates are less expensive. We'll be visiting SoWal more often starting this year because we're no empty nesters. We bought our cottages in SoWal almost 10 years ago to enjoy with the kids until they went off to college and then to spend time in as adults as retirement approaches. Mission accomplished!