My short-term rental Journey
I have been a buy and hold investor since 2011, with a portfolio consisting entirely of long-term rentals. In 2026, my partner and I decided to take the opportunity to diversify our portfolio with the purchase of a small condo in Kissimmee to be used as a short term rental (STR).
I have been sharing this journey, with a previous post and getting insurance for a STR and have gratefully received several sage suggestions and advice on where to look and what to look for.
In this post, I want to share some aspects of my journey in setting up the STR. I recognize that and easy way to do this would be to farm out the set up process to one of the many service providers or property management companies operating in the area. However, we were looking for first hand experience of the process that was involved.
The process started with our orientation into the Condo community. This was set up by the HOA's property management company. We asked pointed questions about whether STRs were allowed and what processes existed to support it, including gate passes to enter the gated community, pool passes and available parking areas.
We also requested a letter on the HOA letterhead to say that common areas such as stair walkways, balconies and railings were the responsibility of the HOA. This is important, because Florida Department of Business and Professional Regulation, (FDBPR) which issues the License to operate a STR, requires a balcony inspection certificate for buildings that are three or more stories high (even if your condo is on the ground floor). One way to get an exemption is a letter from the HOA to say that the balconies are common areas and that the HOA is responsible for them. The License fee was $160, but and application fee of $50 and a Hospitality Education Program Fee of $10 brought the total to $220.
It is important to note that you need a tax registration number from the Florida Department of Revenue in order to pay the sales taxes required from STRs under current law. You cannot complete the FDBPR application for the License without the tax registration number. The tax registration number takes 7-10 days so, there is need to build this into your timeline.
The next step after the application for license is that the FDBPR may need to send an inspector out before they issue the license. In my case, the license was emailed to me within a day of the completed application. I suspect that this was because there are other STRs that were already operating in the development and had already undergone inspection?
So, while the statutory requirements were being met, we were simultaneously working on what we wanted the unit to look like….what was our unique brand? Well that will be the subject of another post!
However, in the meantime, I would appreciate and advice or suggestions you might have from your own experiences in setting up and operating STRs in the Florida area or indeed in any other areas.