Seeking Advice on STR Investment in Kissimmee and Downtown Orlando

[Erene Massart]

Hello, BiggerPockets community!

I am interested in purchasing a new investment property and have been pre-approved for up to $700,000. I am currently looking at options in Kissimmee and downtown Orlando. Initially, I was focused on multifamily properties, but after doing more research and considering that I will be making Florida my primary residence, I believe that house hacking or short-term rentals (STR) may be the ideal route for me.

i still will own my Southern California home; shift it to secondary. Only renting out an ADU on that property.

My plan is to purchase a home that I will hold onto while hoping to gain both forced and time appreciation. I’ve noticed that Kissimmee has homes ranging from $300,000 to $700,000, but I’m curious about whether this is an ideal location for STRs. Is the market overly saturated? I’m trying to familiarize myself with the area more thoroughly.

it seems to have a stable increase in prices.

Since I plan to live in the property initially, breaking even in the first year is my main goal. (5% down; PMI removed with renovation)

However, I’m also wondering if it’s feasible to have some cash flow from such rentals, or if the risk of vacancy is high in this market.

Any guidance or pointers from those experienced in this area would be greatly appreciated! Thank you in advance for your help!

[Alice Horn]

Good morning @Erene Massart! We are property managers with homes throughout Kissimmee and also in Orlando near the convention center and Universal’s new theme park, opening in May. Happy to share the pros and cons of the various communities in both counties.

Orange County (Orlando) places severe restrictions on most vacation rentals, with a few exceptions - so you'll want to be careful there. Osceola County (Kissimmee) has many options in purpose-built, legally zoned STR communities. These communities also feature amenities which make them appealing to Disney families, such as club houses with pools,restaurants, lazy rivers etc.

The area is indeed saturated, but keep in mind it is also the most visited vacation destination in the U.S. Savvy investors can find pockets of opportunity within the market. For instance, the area closest to Disney is actually less saturated and has many homes that can be renovated to a high standard and will book well.

A bit further from Disney, in newer communities such as Solara, Windsor at Westside, Windsor Island and others, you can find deals in this market. Look for ways to make the home stand out - unique theming, advantageous location in the resort near the clubhouse, or with a view. Lakefront or forest view properties perform better.

With an effective dynamic pricing strategy, you can still achieve solid occupancies in this market. We’re seeing occupancies in the 70%-75% range.

Happy to jump on a call to better understand your needs and also take a much deeper dive into the options. PM me and we can jump on a call!