This is about as close as is gets at GW to a section remotely for a landlord question ;)

You are absolutely right, you will have a tough time renting in Feb. I had a tenant bail on me in late Nov once, by sheer luck I found a senior couple w/no kids who wanted to move in January. Otherwise the prospects were not there. I always renew my leases in warm weather (typically May/June) for that reason. Kids out of school for the summer, easier to move, etc.

Yes, absolutely keep his deposit. (I normally wouldn't add this to a landlord but since you're asking if you can keep it: double check the language on your lease to make sure it includes breaking the lease, lost rents, and not damages alone. If you used a preprinted form then breaking the contract will be covered.) If he leaves you will need to send a Termination of Lease Notice (send it Certified w/signature required and hand-deliver a copy as well). If he rejects the Certified and it comes back to you, keep it in your files unopened. State in the Notice that you're retaining his Deposit for breach of contract and lost rental income, then list the date the lease ended and the early date he bailed out. (If you need a sample form to use click on my ID and email me, I'll send you one.)

Technically, not only can you keep his deposit, he owes you rent till the end of the term of the lease (a binding contract), even if he's not living there. That would mean going to court to collect. If you did manage to continue collecting even if he bails, a landlord is expected to re-rent so you could only hold him liable for rents owed up until the day you get the unit occupied with a new tenant and start collecting rents from new tenant. (Can't collect double rents.)

Can you at least get him to hold off till March or April? Consider letting him pay Feb in installments or at a reduced rate? If he bails in March, you've got that month covered with his deposit (providing he didn't trash the place). By April the weather will be breaking and you'll be in a better place to rent it. It really would be in your best interest to try to keep it occupied till the weather breaks. You'll have to weigh rents you get versus no rent, and ask yourself if partial rent is a viable option. Keep in mind you'll have utility expenses on top of cleaning and advertising, you'll have to keep some heat on while it's vacant so pipes don't burst.

I've had tenants make serious noises about leaving in dead of winter either because a roommate on the lease bailed unexpectedly or one long time tenant lost his job. I got flexible at that point, because some rent is better than no rent in Jan/Feb in the Chicago area ;) In the one instance I let the remaining roommate pay in installments (they borrowed from a friend) and in the other I gave the guy who lost his job a reduced rate (50%) just to keep the place occupied and buy another month closer to warmer weather. Both times it worked out, within a month the one tenant secured another job and the other situation the tenant found a roommate. It helped the the tenants and me. I made sure it was crystal clear up front it was a one time deal, that I have expenses to meet that come out of rents, etc., and I was not doing this as a favor to my tenants, it was for my benefit. They respected that and didn't push for more.

If he does leave and you re-rent, do what you have to so the next lease does not renew in winter.