Short Term Rental (Airbnb and such) in Provincetown Cape Cod

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I've been going to Provincetown, Cape Cod twice a year for the last 12 years and watching the weekly rental triple or more over the years. I think it's time for me to own a place and use it when I go there, and rent it out for the rest of the year. Any advice for STR in the Cape Cod, Provincetown in specific? What strict rules and regulations I need to know? Thank you in advance!


I grew up there and I don't know of any rules and regulations but I do know that P-town is ONLY an 8 to 12 week town.  By that I mean that that out of the 52 weeks of the year there are only about 8-12 weeks (summer time) of high rents.  You could get some perhaps around the holidays but not much.  Be very careful you budget for those 8-12 weeks taking care of your mortgage and all the other expenses for the remainder of the year.  

I've run the numbers myself a few times and couldn't really make them work. 

It's crazy how right after Labor Day it's like someone pulled the plug on a raging party. 

My friend rents his place year-round in Ptown and is cash-flow positive for 10 of 12 months.  I'm closing on a place in a few weeks with Airbnb being a key component to making it work.  Do lots of due diligence and talk to people in the know.  You should have no trouble renting during the summer months.  Plan for 10 weeks and be fortunate if you get 13.  If the numbers aren't even close for this time period, find a different opportunity.  The key is shoulder seasons.  May, Sept, even Oct and theme weekends into Nov/Dec could make or break your numbers.  So I'd pick a place that stands to rent during this timeframe, meaning convenient and walkable to the primary places that people would go then.  Value parking over outdoor space.  And a couple things we learned - you need to register with the town, get a rental occupancy certificate, and adhere to the rental limits (although people clearly push those boundaries, the town could come after you).  Good luck and LMK if you wanted us to kick around ideas (I'm married to a MA Broker / Real Estate Attorney)!

@Adam Harper You might find better advice by sending some hosts on AirBnB from the area the same question and hoping for a reply. Find someone that owns 4-5 properties and has a ton of reviews. I’m the resident Pigeon Forge Gatlinburg expert as proclaimed by king @Paul Sandhu . Find the Me of your market and hope they’re talkative. Posting here was a good move but you’ll find mode people that are doing what you want to do by looking in the spot they’re doing it. AirBnB. Good luck!
@Lucas Carl thank you for your suggestion. I think asking your would-be competitors would be a bad idea, don’t you think? Ptown is a very small town everyone knows everyone’s business. As an outsider I think I would be ignored. I might be wrong.

@Adam Harper  I get no benefit from helping people in my market but I do it every day because I enjoy it. Ok so my benefit is enjoyment lol. If you don’t ask you’ll never find out. 

The best way to get better at something is to ask someone whos good at it for advice. Or read books. Or both. 

@Lucas Carl I love your positive attitude! I am new to VR investing. I have 2 air BNBs in atlanta (house hacking - terrace apartment downstairs and I rent out my house when I go on vacation). Thinking of buying a place in Provincetown but the air dna software I use keeps guiding me to pigeon forge which seems to be your expertise ?