You can always make an offer - just because they are asking $X.XX a month does not mean it is set in stone. We wound up paying $2500 for 4 months about 5 years ago - when I looked at the owners listing on VRBO he was asking $1000 a month. And HE made the offer - we didn't even have to bargain.
The key is to be in an area where winter is OFF season. This would not work in most of Florida. Here in southern Alabama, winter is off season.