Well, depending on your tolerance for risk and the amount of free capital you have to invest, owning a vacation property can be a good investment even before you retire. When we were looking on Grand Cayman, several of the properties (especially the newer ones) were being marketed primarily as investments. In our building, several of the owners own multiple units - one primarily for themselves and the rest as investments. A couple of them did this many years ago, and over the years they have essentially paid for their places via rental income, especially by renting it out during the high season when rates are double. Some bought before they retired, rented for many years to pay for the place, and then started using it more or entirely for themselves after retirement. Our property used to be owed by someone who used it only a couple of weeks per year, and the revenue they generated was more than the total cost of ownership, including the opportunity cost of tying capital up in the property. Given the appreciation over the last 10-15 years, I wish I had purchased several. Another part of research, if you do intend to rent out when you are not there, is the demand for rentals and the growth trends in tourism. Grand Cayman has been growing in this regard for a few years, and the last couple of years have set records for short term stays, so it's been a good rental market. And if you are using it only a couple of weeks per year, you might be able to write off part of the trip as you are going down to view and manage your investment. Just wanted to add some thoughts to keep you up at night