Hi Mike:
Transient rentals are only allowed in specific locations. Other properites can be rented long term. Month-month. 28 days or longer. There is a great demand for these rentals, especially during season. There are many great deals in all areas of Key West at this time. Please contact me either by email or phone. thanks!! http://www.kwisland.com

Hi Mike, i
You will need to make sure that rental are allowed in the area you are purchasing (for example, some condos do not allow rentals)
If you are looking to rent your home for more than 30 days per rental, you will need an occupational license from the city of Key West. Currently less than $20 per year. Key West Occupational License Division .......... 305-292-8131
If rentals are less than 6 months, you will also be required to file and pay a sales tax return on the rental.
I would love to help you find your home in Paradise (and with any other questions you may have - please contact Derek Norman at 305-797-3387 or islandhomes@hotmail.com. http://www.WeSellTheKeys.com

Thank Troy for responding!!

I'm confused. I assumed you went to the city to apply for a Non-Transient Rental License. Are you saying you need to get them from someone no longer using theirs? Do you have to pay for them and if so, how much?

Non-Transient licenses are not the hardest thing to get these days, timing plays a very big factor. In the sence of if they are available at that time. You just need to ask and I will find one for you.