@Eric Army
I've done the math on vacation rentals and they've never seemed to make sense to me. I think that if you could rent it out during more than one season it may be worthwhile, but the conversation that prompted me to do the math was in regards to having a house on an island off Maine called Vinalhaven that we visit frequently. I determined it to be one of the rare instances regarding real estate where I would prefer to rent than own.
In that situation, we could probably expect to rent a house out for the same amount each week that one might otherwise get per month if a typical 12-month lease (on an equivalent house, or a house that costs the same to purchase and rehab). Sounds great at first, but goes downhill from there. For example, if you rent it 12 weeks out of the year (just as a baseline for comparison), you're bringing in the same revenue as with a 12-month lease. However, with a year-round tenant, they pay the utilities, they take care of lawn, snow, trash, and cleaning, and they provide their own furnishings. With a vacation rental, you would have to pay for the landscaping, cleaning (every week between tenants), utilities, etc. AND you would encumber the additional expense (whether hired out or the opportunity cost of your own time) to find new lessees each week. Furthermore, if it's a summer rental, you'd have to winterize the house for the winter, which in my opinion is bad for houses (feeze/thaw expansion and contraction is bad for interior paint, wood floors, etc). If it's a winter rental, you'd have the additional expense of heating the place. Furthermore, not sure on this one, but I'm willing to bet that your insurance company is going to charge a higher premium for vacation rentals for both the casualty and liability portions.
All of this suggests that you would need to lease it for enough weeks out of the year to compensate, above what you could expect to make on a year-round rental of the same acquisition and rehab cost, for all of these additional expenditures. So unless it is a 2-season rental (something in the Lakes Region that is also near enough to ski-resorts to attract some winter renters), I think you'd be hard-pressed to make the cash flow equal a 12-month lease type of investment with the same cost to acquire and stabilize, let alone achieve the additional cash flow necessary for the hassle of a vacation rental to be worthwhile. Maybe a cabin in the White Mtns with no heating system, some sort of pump-type well, and a strict carry-in carry-out policy would yield greater ROI, but how much could something like that rent for?
It is my estimation that people who own vacation rentals are typically purchasing them for their own use and then renting them out alternatively to recapture some of the costs of ownership ("I rent it out several weeks per year and it pays the real estate taxes") and perhaps get some write-offs on repairs and improvements.
@Claudio Golia
As far as condos, take a close look at any that you consider. We own a single family home in an HOA called Eastman in Springfield/Grantham. It's beautiful. Private lake, golf course, hiking trails, cross-country skiing, restaurant, fitness club, you name it). Unfortunately, the monthly rent it brings in is maybe $50 more than it would be if it was outside the Eastman Community Association, but the HOA fees are over $3K per year. It's like paying real estate taxes twice. Needless to say, it destroys the cash flow. It literally brings the Operating Expense Ratio (with assumptions for Vac, Mgmt, R&M, and CapEx included) from a desirable 42.2% to a painful 69.47%. I'll sell it to you for 15% under FMV if you're interested...
Just my 2 cents on this chilly October morning.