When Should I begin Marketing - Property Not Available until October

Question

Good day! I'm a new real estate investor. Inherited a 2 BR TH property in a resort town that also has quite a few year-round residents (Ocean City, NJ). In 2025, I have been able to find some vacation rental tenants, however due to assessments, the property is not profitable at the current occupancy rate. What I'm looking to do is have annual or multi-year tenants occupy the property to ensure that I have a steady cash flow throughout the year. The property will be occupied through the end of August 2025, and thereafter I want to get an annual (year to multi-year lease) tenant to move in. I'm thinking that October will likely be the soonest available month. Regarding the marketing of the property, when should I start listing for October occupancy? I was thinking that if I do it now (May 2025), I will have until late June to actually show the property. In July and August, I have seasonal tenants and I don't really want to intrude on them with showings. The next available time would be September to show the property, however I feel that may be too late for October. This also begs the question "Does it make sense to list a property for Fall/Winter move in, or are there more ideal times"?

Taylor Wilson · Answer

Agree with Greg on targeting early/mid August for marketing and showings! Renters often view a high number of days on the market as a red flag so if you do decide to list the property now, I’d recommend removing it later and re-launching with a fresh listing in late July or early August for better results.

Greg Kasmer · Answer

@Daniel Alvino - From my experience it's very difficult to start a lease December, January, and February, so you really have October and November to start a lease with reasonable demand. However, I'd really target October instead of November if I were you.... I've found that "better tenants" look/plan ahead better than tenants that look last minute. Ideally, to start a lease 10/1, I'd look to start showing the house in early/mid August. I've been vacationing in Ocean City, NJ for years so know it fairly well. Is their a Saturday in August in which the vacation tenants are "turning over"? If their is any longer term tenant interested at that time perhaps you can show them the house while it's being cleaned on a Saturday? If I were you I'd start marketing the long term lease in late July time period and try to get any potential tenants in there in early August to take a look. Alternatively you can also do a video tour and have great pictures taken. Some tenants may be interested enough based on that information to apply and if they meet your criteria they could do just a quick "walk through" in early September. Lately, I've also been a big fan of virtually staging photos to show the house/apartment with furniture just in case there is not furniture currently in the house/apartment.  Hopefully this gives you some ideas to consider! Good Luck!

Daniel Alvino · Answer

Thanks @Greg Kasmer and @Taylor Wilson. Another challenge that I have is that the summer leases that I have are month long, so essentially tenants are both there until month end or so. I will look into getting a video tour so I can do some virtaul showings while the place is still occupied.