Larger house outside DSW resort or smaller inside resort for STR?

3 Replies

So I am new to investing and have been reading materials, listening to podcasts on BP. I would like to purchase a STR in Kissimmee, FL area. Originally thinking 4 BD 2bath min, with pool. Willing to spend on updating/upgrading the interior as needed (and reasonable). Question is this: From an investment perspective, is there better chance of success (keeping "some" positive cashflow) owning the above property in a resort community with high HOA's or a larger 5 or 6 BD with more sqft in the same zip but not in a resort, low to no HOA?? I am in Bay Area, Ca so would hire a local management company.

It seems larger houses bring in more cash but I am not comfortable yet with occupancy rates since AIRDNA, Craigslist, ... seem to be very different.... 

Thanks in advance, any insights will be appreciated. 



@David Maranhas I can’t answer your exact question but it does raise some red flags. Why would you buy something only to rely on “some cash flow?” If you’re using a PM in FL you’re likely to be losing cash every month.

Where did this idea come from?

Keep reading and listening. 

I own two properties in Kissimmee and manage another. Contrary to Lucas' belief, you can lose money with property managers but not if you pick a good one. What type of clientele are you looking to cater to? We have a property in Reunion Resort and people seem to seek it out and are familiar with the resort. You can also find properties outside an HOA but be really careful of the neighborhood you select. I was attracted to the idea of no HOA fees and looked at house outside an HOA but then saw the way the neighbors took care of their houses (or didn't, rather) and knew it wasn't a good fit for STR. The regulations in the area can be very different depending on the location so be sure to understand the ordinances governing the location you're looking to buy. The biggest thing I see is that there are a lot of properties in the area so if you can find something unique, that's a better bet than finding something like all the others where the only thing you'll have to compete on is price. Let me know if I can help.

Thanks for the responses Lucas and Wendy.

Originally the plan was a vacation property (family & friends on both coasts really like the area) and STR in hopes to at least break even (I would purchase based on LTR income potential, just in case). But, seems like there is opportunity to make quite a bit more with STR (Vs LTR) for the right property.

I understand it is best to be close to the attractions, preferably in gated, managed community , as Wendy highlighted concerns with neighborhoods.  Seems to be a variety of resorts with a variety of fees and I am curious if the all out vacation resort rentals have much higher occupancy rates vs a community with maybe a park and pool. I would think after a busy day at the attractions most would just want to relax in a comfortable, clean quality house in their own pool...but, I could be wrong and the club houses, arcades, water parks, bars, theaters...could attract more vacationers..