Vacation/ Short Term Rental in the Caribbean

[Derek Davis]

I am interested in buying a beachfront condo in the Caribbean to use as a Vacation property/ Short term rental.  The long term plan would be to hold the property as a retirement destination for longer stays after it is paid for.  Does anyone have experience doing this?  I mostly would like to speak with someone about how they determined which islands they considered investing in and which islands they ruled out and why? Looking for just general advice or conversation on restrictions related to foreign purchases, short term rental data for certain areas, lifestyle and convenience as a retirement location, etc?

[Jeff Wagner]

I may be biased, but often times people forget about Puerto Rico and the US Virgin Islands.  In my view, risk is reduced by owning in a US flagged territory.  As example, in the USVI we have fee simple ownership, title insurance + contract and closing process similar to the mainland.  Puerto Rico has more nuances, including spanish language long term ground leases, but is also US territory.  I personally evaluated several central american and caribbean destinations before ultimately settling on the USVI.  To add to @Brooklyn McCarty's point, AirDna seems to be ok for here as well, easy way to check rough numbers.