Don't confuse a life style decision with an investment. Look at initial fees like land transfer taxes or legal fees, and then ongoing property taxes and management fees if there is a rental pool. Look at mortgage options as often there are few or they are far more expensive than in Canada. As such often the best is to get an LOC on your Canadian house then buy in cash.
You will find in most cases there are better investments elsewhere from a pure monetary point of view. But as it is meant primarily to enjoy yourself then the monetary aspect is less relevant.
Look at flights there and activities (such as restaurants and shops), in season and outside the main season, as many areas have hurricanes, terrible weather or rain and thus far fewer people at certain times of the year. Some areas have squatter rights and security issues, both in season and especially outside the main season.