I get emails occasionally from people who ask about renting a house or condo here for winter months and based on the suggestion of Dan C. am posting the information here that I typically give in response.
House and condo owners that want to rent during the winter months are restricted on how long they can rent for by their community and city. The restrictions are usually that they have to rent for a minimum period and in some cases, mostlly in condo communities, they have to get association approval for each renter. Typically you'll find that the minimum rental period is 90 days or more. Some beach communities allow 30 days rentals and occasionally you'll find one that is a minimum 7 day rental. One thing to keep in mind is that if you rent for less than 6 months and 1 day you will have to pay a state tax of (I believe) 11% in addition to the monthly (or weekly) rental amount.
You will also need to find out how much of a deposit you have to put down and if it is refundable if you need to cancel, if there is a key deposit, if there is a cleaning fee, if there is an application fee, if there is an association application fee, what kind of parking there is (if you'll have a car), if pets are allowed (if you are bringing any) and what utilities are included in your rental fee. If you don't see this information in a listing or an advertisement you should ask.
In my experience most owners of short-term rentals don't put their properties in the MLS because they don't want to pay any fees to realtors. There are some listings for short-term rentals but you need to be aware that in many cases the rental amount showing in the listing is often for a 12 month lease and that shorter-term rentals have a higher rental amount. In addition to that, rental amounts are often significantly higher for the months of January through April. Some listings will state what the rates are for shorter term rentals and for those peak months, but some will not. You can search through the rental listings for this area on my website by going into the MLS search and then clicking the top tab for Rentals.
There are also websites where vacation property owners can advertise directly and I often refer people to those, especially if they are trying to find something for a very short-term period like 1 or 2 months. The best known one is Vacation Rentals By Owner. You can also find other sites by searching for Vacation Rental by Owner in Google or any other search engine. The properties are usually broken down by state and city to make it easier for you to search.