My parents owned a home on Shelter Island, on the eastern end of Long Island, for years. And each year they would rent it out for the season (Memorial Day to Labor Day) to one tenant, or in two-week to one-month increments, and move back to their 300-square-foot Upper West Side Manhattan co-op studio, thinking of it as a summer getaway. As “reverse-commuters,” their rental income over the summer paid for the costs of homeownership for the rest of the year for both residences. Quite often, they would get the same tenants, and by the third year, the tenants bought their own house. It was common practice to test the market by purchasing before investing in it.
It used to be said that if a summer rental home wasn’t leased out by the preceding February, it was a weak rental market. This year, there are thousands of summer rentals remaining on the East End, and market participants don’t seem too worried about it. Why? Rentals are being leased at the last minute rather than way in advance. This past Memorial Day Weekend, there was a surge of rental activity and the same is expected for July 4th. One explanation could be that the market is softer and would-be renters are waiting until the last minute to get better deals.
However, I recently spoke with Judi Desiderio, a friend and East End real estate expert, about this pattern. Over the years, she has observed that the latest generation of would-be summer renters is increasingly treating the process as they would order items on Amazon. They don’t stock up on basic goods like toothpaste and mouthwash in advance. They can easily reorder more at the last minute and get it the next day for free. They rely on “just in time” inventory management and apply that way of thinking to renting properties out east. There was an unusual surge of rental demand after Memorial Day weekend, with the final rush expected just after July 4th. I suspect this pattern has evolved since the pandemic and is here to stay.
Behavioral change by generation
My personal experience with the generational behavior was shared by my dad years ago when we were riding the NYC subway together. As someone from the silent generation (he was born in 1935), he pointed out that his generation gets up from their seat two stops from their station. Being a Boomer, he observed that I would get up one stop before my station. Later on, when my wife and I grew to have a family of four sons, I observed that my three millennial sons would get up as the train pulled into the station, and my Gen Z son would get up as the door opened at his stop. I have thought of Boomers like myself as always demanding immediate gratification, so getting up early for a subway stop didn’t seem like a contradiction, but here we are.
The result of this shift is much greater anxiety for rental landlords as they wait for their homes to be leased at the last minute, even in an active market.
At The Money podcast: Consumption of summer rentals
My good friend, prolific blogger and podcaster Barry Ritholtz, invited me onto his second podcast, At The Money (ATM, get it?), to talk about summer rentals. You should subscribe to both (on one feed). He has a second home in the Hamptons, and I cover that housing market for the local MLS there, HREA.com, so that is where we began our discussion.
But we also touch on other markets. The same macro rules I shared in the Hamptons seemed to apply to most second-home markets across the U.S. Markets that skew higher-priced, considered “luxury,” or, at the very least, the upper half of each second-home market, seemed to be showing more rental activity. For sales, market segments with lower dependence on mortgage rates (which are currently rising) also help skew that demand toward the upper half of the price range.
Final thoughts
The East End summer rental market has shifted from early, predictable leasing to a last-minute, “just-in-time” model, with renters increasingly booking around key holidays rather than months in advance. This reflects a generational, Amazon-like consumption pattern more than weaker demand, though it creates greater uncertainty for landlords. At the same time, the trend likely shifts some pricing power to renters, is enabled by low-friction technology platforms, and may push the market toward more flexible, hospitality-style rental strategies, potentially weakening the traditional renter-to-buyer vacation home pipeline.
The actual final thought When we think of digital paper format size used for lease signings, consider this.