Our primary home is in Michigan, but after I retired we decided we wanted to get out of the snow and ice during the winter months. So we rented along the Texas coast for several winters..........enjoyed that, but eventually decided to try the Florida Gulf Coast. Rented there for one winter, and really loved the location and the people. Great spot for kayaking, fishing, and the people were super-welcoming and friendly. We intended to keep renting the same house for the next few winters, but a neighbor came over one day and told us we HAD to look at a house that was going to go up for sale very soon, next to his house (this was 3 years ago now). The 92-year old guy who had lived there passed away recently, and his son did not want the house. His preference was to sell it quickly if possible. I really had no plans to buy a house down there, but we looked at the house (it was structurally sounds but needed some updating and repairs here and there), and asked him what he wanted for it. He said if we were able to pay cash, he would give it to us for XXX, which seemed like a fair price for the place. I still was not sure I wanted to buy a house down there, but my wife (and the neighbor) talked me into it. We had the place inspected (it passed), and talked to a contractor about how much $$ the priority work would cost (it was reasonable), so we took the plunge and bought the place. It's not like me to make quick decisions like that, but it has turned out well for us, and we have no regrets. We spend our winters down there now, and we love it. It's just a small house, but it's perfect for the two of us. When we are back in Michigan, we rent it out on VRBO/AirBNB (we have a great local property manager - I would not rent it without having that). The rental money we take in pays the taxes, utilities, and more, so that's been nice.
My advice: life is short. If you think you would really enjoy a vacation home, and you can swing it financially, do it. Renting is okay, but when you own a place, you can really make it your own, and there is satisfaction and pride in that. We get comments all the time from people that rent our house saying how much they love the place, and the location, and that makes us feel good. I don't know how long we will own this place........hopefully for quite a while, but we have already gotten a lot of enjoyment out of it.