Have used vrbo and similar sites for FL, HI, CO and Grand Cayman. We tend to rent longer term and find that we can negotiate an excellent price with owners for longer stays. Have also used for weekly rentals. Have never had problems but always call the owner first to get a "feel", check with the property if possible to make sure that person is really the owner and free to rent, and would never rent anything with no photos. All properties have been as good or better than described. As previous posters have said, check around, then decide.

You are correct that every condo owner is an investor of some sort. But it really does matter why the owner bought the property. If the place is strictly for investment then the owner will only put in money when he has to do so and not keep up the condo as well as someone who spends 6 months of the year in the condo and rents for the other 6 months. The strict investor will put as little money into the place as possible and you'll have a spartan condo old tired furniture and furnishings. A warning sign here is a condo complex where almost all of the other rentals are run by a specific management company except for this one. It may be that the condo was kicked out for not keeping up to standards. If you hear an owner taking pride in the property and telling you all of the upgrades and extras then that is a good sign that he cares about the place.

At least in Hawaii there are a number of people who have bought and the rent doesn't cover all of their expenses. Property values have risen so much that they make the money back when the condo is sold.