I know that it's not advised to have investment properties that have an HOA. But I was just curious if anybody has had any success stories? I live in Naples, Florida, where a lot of the communities are gated. I had an opportunity land in my lap that seems like not something I would want to pass up, but just curious if anybody has any feedback besides just saying no to the property because of the HOA. The house had been rented or used as an Airbnb in the past, and I do have the availability to see those transactions.
Really depends on the HOA… I live in Naples and in an HOA, the HOA dues are $350/Year and STR’s are allowed. A good deal on a house in my neighborhood (or a similar one) would make a great investment property… I own a Real Estate Brokerage and Property Management Company so feel free to reach out with any questions…
I know that it's not advised to have investment properties that have an HOA. But I was just curious if anybody has had any success stories? I live in Naples, Florida, where a lot of the communities are gated. I had an opportunity land in my lap that seems like not something I would want to pass up, but just curious if anybody has any feedback besides just saying no to the property because of the HOA. The house had been rented or used as an Airbnb in the past, and I do have the availability to see those transactions.
Lindsay — good question, and one that comes up often in Florida since so many properties sit in gated communities with HOAs.
The “no-HOA” advice is mostly about control and risk:
• Rules can change — some HOAs suddenly ban STRs or add rental restrictions.
• Fees can increase, cutting into your cash flow.
• Enforcement can be strict, which adds friction if you’re trying to run it as an STR.
That said, there are success stories when:
• You verify the CC&Rs/bylaws and confirm STRs/long-term rentals are allowed.
• The HOA is financially healthy (review their budgets/reserves).
• Past rentals in the community prove demand (sounds like you already have that data).
If all three boxes check, an HOA property can be a solid play — especially in a market like Naples where STR demand is strong.
On my side, I help investors with STR and rental financing (DSCR, bridge, etc.), and lenders will want to see the HOA docs too. If you want, I can walk you through how to underwrite this deal factoring in HOA dues so you know if it still cash flows with today’s lending terms.
Curious — are you leaning toward running this as a short-term rental or a long-term hold?
@Lindsay Fitzgerald I'd make sure to dive into the documents on the HOA; we have properties in an HOA; 4 of them are in one, which the HOA has been miserable to deal with on the STR side of things, on the LTR strategy it has been fine. Long story short, they didn't have anything in their documents against STR, yet told us we couldn't and when we pressed, they passed new rules against it.
We have a house in Naples in an HOA that was our personal home and we just turned it into another rental when we bought another home. For LTR, haven't had an issue. Even if the owners of the current property were using the home for STR, if the HOA docs don't allow it, you may be forced to pivot if STR is your focus on that investment.
If you are free this evening, there's a Real Estate group meetup at innovation hotel, and you may find more local people that have input as well. Feel free to send a DM and I'll get you the details.