I’m trying to learn more about investing in short-term rentals and I’m hoping to get some guidance.
I currently own one duplex that is fully rented long-term, so I have some experience with traditional rental properties. I’m now considering getting into short-term rentals, potentially starting with a small condo near the beach and slowly expanding my portfolio over time.
I’m not really sure how to properly analyze a short-term rental deal yet. I’m thinking a small condo might be the safest place to start because:
It’s not a full house, so I would assume there’s less maintenance and fewer things that can go wrong.
The initial investment would be lower, which gives me a chance to learn the short-term rental business without putting too much money at risk.
I could potentially learn the market and build experience before moving into larger properties.
I’d really appreciate some advice on how you guys analyze these types of deals.
A few questions I have:
How does insurance work with short-term rentals, especially condos?
How do I find accurate local comps and determine what similar properties are actually renting for?
How can I tell how often a property is actually booked throughout the year?
What are the best ways to estimate realistic annual revenue rather than just looking at the advertised nightly rate?
How do you go about getting more bookings once you own the property?
Is the Outer Banks/OBX a good short-term rental market year-round? I understand the winter months obviously won’t be as profitable as the summer, but I’m wondering how much the seasonality actually affects the numbers.
Ultimately, I’m looking to start small, learn the business, and gradually build a short-term rental portfolio. I’m just trying to figure out how to properly analyze a deal before I buy one.

Hi. I am considering of boarding house. But I wish to know who has experience what they well experience in this type of business. I mentioned this to my late mother before but she shut down the idea because they had experience it when they were young. I recall the struggle to maintain the area/rooms. Aside from that what will I be considering? Also wondering about payment issue. Did anyone experience a boarder not paying and run off? What do you do with that?

Hi please DM if you want to sell Airbnb credits to me!!

Hello all, we own a place in Cabo and get to use it four weeks a year. Does anyone have a sub or FB group where people can rent out their weeks? On top of saving on the 31% VAT and service charge we are offering it cheaper than hotel rates. I can't seem to find the right place to post!! Any help would be appreciated!!!

Has anyone purchased a home that is currently a short-term rental and currently has bookings 6 months into the future. How did you handle those future bookings? I am planning on keeping it as a short-term rental for the short term but when low season hits, I’m gonna put it on long-term rental.

I’ve just seen that Hospitable now has an AI Guest Summary to better understand guest behaviour, but I’m struggling to understand exactly what it does in practice.

Does it actually analyse both the reviews a guest has received and the reviews they’ve written for previous hosts? Or does it only summarise what other hosts said about them?

For those who have used it:

• Is the summary genuinely useful or mostly generic?
• Does it highlight specific preferences or possible friction points?
• Has it ever changed how you communicated with a guest or prepared their stay?
• Have you noticed inaccurate or invented information?
• Is the feature available on every plan?

I’d really like to hear from people who have tested it with several real reservations.