Love Hawaii, even though we go 2-3 times per year, I never grow tired of it. I also love Florida coastal and definitely Disneyworld. I could move there easily, and we could actually afford Florida.
We have friend who bought a full condo on Maui, oceanfront, and it was tempting to do the same thing. Very tempting. I think it was $450K, but it's tiny. It's big enough for a vacation home (king bed is a real plus) and has a full kitchen and nice living room. It's bigger than a Westin studio, but not as big as a one bedroom at Westin.
They have a company renting the unit, when they aren't there to use it. I think they are doing well with it. They eventually want to stay longer. I don't know if they want to pay it off early. They are living the dream for sure. They have a cabin in the mountains, very close to the bigger towns. of Silverthorne, Dillon, Frisco and Breck. So both of their homes are vacation homes. They had to get rid of a lot of stuff, when they sold their house in Denver. I could not do it.