I'm new to Trulia and almost 99% a Buyer's Agent but I don't think any listing service allows one to select two categories. But I happen to have two clients who are looking specifically for rental property right now and so I appreciate your conundrum.
I think your agent is right that more folks are looking for second homes rather than pure rental plays. But my two clients are the exception to that rule, and the local MLS does not have a category for Rental Cabin.
So, my, less than perfect suggestion, is make it Residential in the MLS and Income/Investment in Trulia and Zillow (for a month at least) and see what happens..
Speak with your Realtor to go over the options available in your local listing service (we call it MLS here in Massachusetts). You really want to market the property as its "highest and best use" to obtain the greatest amount of value for the home. A sharp Realtor will be able to provide you with this analysis and certainly a licensed appraiser would be able to do a highest and best use report on the property. Then once you know the best use, you focuse your marketing towards that type of sale..... more
If you mean on the MLS, that's up to the rules on your local MLS. But the answer's probably "no." You can do a "sale" and a "rental"--and have two listings that way, but not two "sales."
Suggestion: If you're willing to continue renting, list one under "sale" with the comment that seller will be willing to consider owner-financing or a lease-option. But another under "rentals" with a similar notation--that the owner would be willing to consider a lease-option or lease-purchase. Check with your agent to see whether such an approach would be permitted.