The summer rental season may make this a costly proposition. Beach condo rates quadruple during the summer season over the winter season rates, so what you could pay in rent for Oct-Mar would only cover a month and a half during peak season. As an example, a 2 bedroom gulf front condo may cost $1,200/month during January and $1,200 a week during June. For the year this example condo would run close to $29K. If this rate is ok with you, most of the owners would be quite happy to rent to you. You may be able to find a more reasonable rate if you are willing to consider a bay front condo.