Just FYI, property management on a vacation rental will run ~50% of gross. Yes, 50%. So cut your income number for the property in half right up front.
You will also have loads of vacancies even during prime season (last minute cancellations, random gaps, etc) for all sorts of reasons.
So bottom line, I'd assume you'll lose money, probably a significant amount of money. Might be worth it, might not. How much does it cost to rent a place for a week a year and just do your vacation in someone else's money pit?
-W