Revisiting idea of vacation condo

Good Day!

My wife and I keep getting the itch to buy a VRBO'able vacation condo, preferably on the Gulf coast. (MUST BE Ocean front or nothing) We already own 34 units here in our own town of Waterville Maine, but we plan to travel more and more. We are age 52 and are already semi retired and feeling the itch ... the VRBO condo would serve the purpose of A.) Having a warm place to fly off to at a moment's notice as long as it's not rented at the time, as well as a great place to hang out and travel FROM. Sort of a travelers "HQ" if you will. (Flying and cruising from Siesta Key will be pennies on the dollar vs. Portland Maine). 

Questions: 

What are some decent areas on Gulf Coast. We have friends that have condos in Venice but it's not a good place for VRBO's that I know of. 

Is this a good time?? My perspective is that we're again at the "peak" or at least certainly a seller's vs. buyer's market. 

What are the "best" places to buy a VRBO on the West Coast?

Thank you all!