I would try to get to market rate after the holidays, a better time for you if they leave.  

A lowball offer might make dinner on the holidays awkward.

If it's 5PM on the Friday of a three-day holiday weekend, it's guaranteed that I'll get a call from one of the two low rent units, or both.

Im afraid that she will pay month to month then leave in the middle of holiday season/bad weather otherwise.

For me, I just do 1 major holiday, like a card or something. 

My agent contacted me while I was traveling back to Chicago during the Christmas holiday.  

Right now, with Deutsche bank possibly blowing up and an election looming and now going into the holidays, it might not be the best time to throw a lot of money into flipping.

Alabama may be different, but 'in a couple months' will still be in the holidays.  

So without any luck and the holidays around the corner we are considering renting out our current home so we can buy a home here in Florida.

I manually set holidays and special events in outswitch and apply a multiplier to the base rental rate for that period of time.Outswitch can connect to multiple booking channels but HomeAway/VRBO connection can only be done through RentalsUnited, a booking channel aggregator that I'm currently demo'ing but don't have enough experience to comment on yet.