HorizonsFan - things can get a little tricky there. If you're renting out a portion of your points, then it's still vacation home. If it's all of your points, and you do it OFTEN, then yes, vacation home becomes investment property. As long as the main use of the "points" is for vacation purposes(you actually occupy the property), then it's a vacation home . If you're renting out more than vacationing(occupying), then it becomes an investment property and is treated as a completely different animal. This is a timeshare, though it is a real estate interest, things are tricky. For instance, you own a home in NH. If you occupy it for 2 weeks per year, it is considered a vacation (second) home and all income is considered rental, and any mortgage interest is considered deductible. If you do not occupy it for two weeks per year, it is considered an investment property, with you being able to deduct some of the expenses of the upkeep on the property, but not interest on the mortgage.