The Hamptons and Cape Cod — two of the country’s most luxurious and sought after seasonal rental markets — are giving new meaning to “try before you buy.”
Agents in both destinations are working with many high-end clients who end up purchasing after staying at a home for a season or two. Some clients can’t even wait that long, buying what’s available without visiting a property to ensure waterfront-compound living for the summer and beyond. We spoke to Sotheby’s International Realty real estate advisors in both markets about how they’re capitalizing on that demand by offering the sophisticated, bespoke service for which the brokerage has become known.
Shorter Supply, Higher Prices
On the East Coast, the Hamptons remains the crown jewel of seasonal rental destinations.
“The Hamptons have long attracted people from all over the world, and will continue to do so,” says Zack Dayton of the Dayton Team with Sotheby’s International Realty – East Hampton Brokerage. “With so many wonderful areas, there’s truly a place for everyone here. As a local resident, I embrace the season and the diverse visitors it brings. It really contributes to how special this place is. I think the rental market plays a role in that.”
The pandemic often brought renters to the Hamptons for a full summer, and prices peaked. While the area is seeing an extended season, with more rentals starting in June, there’s been a shift toward shorter stays, usually two weeks to a month, and an increase in competition for the best-appointed rentals.
“Move-in ready homes with great amenities tend to get rented pretty quickly,” says Dayton.
Although asking prices have plateaued, a month-long rental on Long Island’s East End could cost anywhere from $50,000 to $500,000.
“We’re also starting to see a few more million-dollar listing prices for the full season,” he says. “That’s been a new trend that we haven’t often seen until now.”
Those properties may come at a premium because many homeowners also want to holiday in the Hamptons, hoping to avoid the hassle of overseas travel and a lack of conveniences such as in-unit air conditioning, says Michaela Keszler, who works with daughter, Paulina, out of the Sotheby’s International Realty – Southampton Brokerage.
This has resulted in a smaller-than-usual supply of homes available to lease, which makes having a relationship with an agent like Keszler all the more important for her clients, especially those who hail from overseas.
“It’s not just renting a house,” says Keszler. “It’s working with clients, finding the right area where they are happy, finding them a house they enjoy.”
If someone is visiting New York for only two weeks but might want to see 50 houses, “of course, we’ll go see 50 houses,” says Paulina, who has already earned accolades since joining the industry. “And we’ll take them to lunch and be their tour guides.”
Renters often end up enjoying their time so much that they want to own a house, thinking of a rental property not just as a place to kick back but as an investment with long-term returns.
Michaela Keszler and her family did that in 1990. The first day they stayed at a Hamptons rental, they put an offer on the house. They ended up buying it. Four years after vacationing there, they relocated permanently from their native Germany.
The Renter-to-Buyer Pipeline
Between the sunny climate and laid-back atmosphere, renters can often turn into buyers once they’ve connected with the lifestyle found on these vacation peninsulas.
“That’s happened multiple times on Cape Cod,” says Ellen Valentgas, real estate advisor with Sotheby’s International Realty – Osterville Brokerage. In 2023, Valentgas sold an ultra-high-end property after presenting the listing to a rental client via email. “I’d say many of my tenants are waiting to buy, but they’re waiting for the right property.”
Last year, Valentgas sold another waterfront rental property after two long-standing summer tenants competed for the purchase.
Valentgas’ clients enjoy bespoke, personalized service, tailored to their individual preferences, which keeps them coming back summer after summer. Her customized “Sotheby’s International Realty welcome” includes ready-to-use beach gear, custom guidebooks, luxury sheets and towels, and an on-call property manager.
“They want to know that there’s someone who will make sure that all their needs are met,” she says. “We make them feel they can enjoy resort-like services in a private, luxury home environment.”
Her area, Osterville, rents for $6,000 to $20,000 a week. In Falmouth, another Cape Cod town, rentals start at $4,500 a week, says Pamela Mullin with Sotheby’s International Realty – Falmouth Brokerage. June provides shoulder weeks, and many are couples looking to reserve an extended stay for family members.
Like the Hamptons, higher-end Cape Cod properties tend to be on the water with views and offer a private beach, adding that these are often snapped up by clients who grew up vacationing on the island.
“Most people who purchase on Cape Cod have a personal connection to the area,” says Mullin. “They’ve spent summers here as children, have family members in the region, and eventually decide to buy. Often, they rent first to explore the various areas, each offering a unique lifestyle, before making a decision.”
To inquire about renting a home or listing your property with Sotheby’s International Realty, connect with us online.