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Updated 5 months ago on . Most recent reply

Excited to be closing soon on our first investment property!
Investment Info:
Single-family residence buy & hold investment in Orlando area.
Currently under contract for a single family home that we will be utilizing as a short-term rental.
What made you interested in investing in this type of deal?
The property's location is ideal for short term rental (Orlando area theme parks and convention centers.)
How did you find this deal and how did you negotiate it?
Found through lots of online research and connecting with an agent who works with investors. We negotiated less than asking since the property had recently reduced price and the sellers were motivated.
How did you finance this deal?
We are using a Debt service coverage ratio (DSCR) loan.
Lessons learned? Challenges?
Not all insurance is the same. Fortunately I work in the insurance industry so I generally knew what to watch out for. However, I still learned a lot since short term rentals have unique insurance needs that aren't always met with traditional policies. Also, pools are going to be expensive. I think there's a lot one can do on their own to maintain it, but it does require diligent effort. Otherwise, hire a pro to help maintain it.
Most Popular Reply

Hi Angela,
Thanks for sharing your experience with investing in a short-term rental in the Orlando area! It sounds like a great opportunity, especially with the location near theme parks and convention centers.
Nice job negotiating a lower price with motivated sellers—that’s a smart move. You're right about the unique insurance needs for short-term rentals. It’s great that you have industry knowledge to navigate that. And pool maintenance can be tricky; it’s attractive to renters but requires diligent care.
Are you planning to manage bookings yourself, or are you considering a property management company? That's another important decision for STR investors.
Best of luck with your investment! Feel free to share any insights you gain along the way.
Jackson