“A lot of times, people have this mentality of, ‘I’ll wait until right before summer, and then I’ll just negotiate a really good deal,’” Tyler Whitman, co-founder of The Whitman & Roberson Team at The Agency, said. “And that mentality hardly ever ends up working out because a lot of these homeowners have made other arrangements for their properties if it’s not rented by the summer.”

Indeed, Whitman — who said he’s “cautiously optimistic” about the Hamptons rental market this year — is not alone in giving this particular, and important, tidbit of advice.

“I would say to start now, because we are seeing a nice, robust response to rentals,” Dunphy said. “And there’s always going to be a limited inventory.”

Demi Reichart, also a licensed salesperson with Corcoran, added, “It’s good to secure rentals now.”

The risk of waiting, Whitman said, could result in missing out on that dream home for the high season.

“You’ll either end up getting a house that you’re not thrilled about, but you’re still paying a lot of money for,” he said, “or you’re going to end up paying the same amount as you would have when you had more options.”

A Tale of Two Strong Markets

Whitman’s cautious optimism comes from seeing positive signs in the East End real estate market, as well as the stock market.

He has already seen high-end rentals renew contracts with tenants from last summer, he said, and there are more in the works. While many Agency listings have already been scooped up, Whitman said that some prospective renters may still be able to afford what’s left thanks to a strong stock market and, in some cases, bonus season.

“Whenever they get their bonuses, they plan their big, fancy vacation with their families,” he said.

Matt Breitenbach, an associate broker with Compass, said his team handled twice the number of rentals in January compared to last year. Some variables are changing the market this year, he said, including the upcoming U.S. Open at Shinnecock Hills Golf Club in Southampton this June.

“The Open is bringing a lot more inventory to the market,” Breitenbach said, noting that a number of new builds have fed the rental market with inventory, making it more attractive to visitors.

Dunphy has noticed that most of her renters are looking for homes for one to two months in June, July and August. She said that she’s seen fewer Memorial Day through Labor Day rentals except for the “extremely high-end” oceanfront properties.

“I think this is because people with kids, they have summer camp, they have sports, so they’re looking for a more nontraditional time frame,” she said.

The rental market tends to change every summer, Dunphy said. In recent years, she wasn’t thrilled with it, noting that it’s already improved for 2026.

“I’ve seen an increase,” she said. “The last three years, I would say two years, have not been a good rental season from what I’ve seen, but I see this year that my numbers are up.”

A Word to the Wise, Homeowner Edition

Homeowners should make sure their properties are in top shape, Dunphy said.

“Make sure your house is as pristine as possible,” she said. “Think of spa hotels, that sort of aesthetic.”

She also implored homeowners to price their homes realistically. “It changes by the home,” she said. “You know, we have such a broad range. I suggest they go online and look at comparable rentals that are on the market and price accordingly.”

Her most successful homeowners who rent out their properties “are being reasonable,” she said.

“They realize if you want to rent your house, you have to be competitive in pricing,” she said. “Gone are the days of COVID pricing. That spoiled a lot of sellers, and they were hoping to be able to repeat those numbers, but that’s not happening. It was crazy for a while, but everyone has come back to reality.”

Whitman finds that a lot of homeowners try to hike up prices dramatically after a successful first rental season.

“Just because you rented last year isn't an indication that you underpriced,” he advised. “It's usually an indication that you were priced appropriately.”

Reichart said that homes with strong photography do well, too. “Some people do rent by the pictures,” she said. “Of course, pictures lure people in, so have nice photos taken.”

Breitenbach said for homeowners, it comes down to price, patience and presentation. “There’s a price depending on how patient you are,” he said. “You can rent it.”

Walkability Is King

The most popular rental spots, agents agree, have proximity to a walkable village — notably Bridgehampton and East Hampton, Dunphy said.

“They want to be able to walk to a restaurant, they want to be able to walk to go shopping,” Whitman said. “And I think that might be residual from last year being, maybe, the worst traffic year here. I don’t know if that was a result of all the construction, or if it was just because there were so many people out here, but now I think we’re seeing a big push toward, ‘I need some walkability from my house.’”

For homeowners looking to list their properties, the same advice that’s given to renters applies: Do it now, Breitenbach said. He called the market “controlled chaos” — adding, “You never know.”

“If anything, you’re kind of on the further end of listing it,” he said. “But it’s not too late by any means.”