I definitely think the rental might be a better way to go, especially if you don't know of a specific place you definitely want to go to. If you rent, you could move around winter to winter and see what's the best. Then you can always buy once you have that all figured out.
My dad is doing this. He has gone to Honduras, Sedona, Biloxi, and a couple spots in FL. He almost bought a spot on an island in Honduras(crazy how cheap it was going to be....something like $250k for a 4 bedroom 3000SF with it's own beach), but now that he has moved around I think he prefers that. This sounds awesome to me unless part of the goal is to get socialized with other folks that live there.
Side note: The thing that keeps me from wanting to buy and rent out my place is that I would basically have to keep the rental vanilla so that others aren't rough ridin' up my stuff the other 9 months a year. I feel like if I buy a place, I want it to be mine. For example, I like to cook. No way am I leaving good pans, good knives, etc there for others to steal or damage. Same with a really good bed and couch or anything else that you appreciate and brings you comfort. If you are going to live in something that feels like a rental, let all the bullshit that comes with ownership be someone else's issue, imo.