The vacation rental realm

Cape Cod Life  /  May 2018 /

Writer: Deb Boucher Stetson

rental properties

Tyler Pybur, Margo Pisacano, Katie Collette

’Tis the season for looking ahead to summer, and for many people, that means finding a summer rental on the Cape or the Islands.

“They’re all looking for that gem,” says Tyler Pyburn, marketing and communications manager for, which has an office in Brewster. Rental inquiries and bookings have been steady, he says, noting, “The larger size homes typically book earlier in the season.”

One “fun new trend,” Pyburn observes, is groups of people coming together for weddings, reunions or other events and seeking to rent a “compound,” or row of houses next door to one another. That way, people can spend time together as a group, holding, say, a backyard barbecue at one of the homes, but they can also have privacy and time alone.

The way works, he explains, is that rental properties are listed on the site with plenty of photos—increasingly, he notes, “People want to see every room”—and then renters reach out directly to the homeowner with questions “to make sure it’s a perfect fit.”

Margo Pisacano, owner of Margo & Company in Osterville, says her firm specializes in both summer rentals and relocations. “We used to be pretty much booked up for the summer by January, February or March. Now people are busier, and we find a lot of last-minute bookings,” she says. “We’ve been doing rentals since 1992, so we’ve seen the ups and the downs and the changing cycles.” One change, of course, is online rentals. Pisacano says there is a downside to that. “You don’t get that hands-on, personal service,” she says.

For the best of both worlds, “We do a hybrid—we encourage our owners to go on those sites, book them, and then we handle it from there, taking care of all the details,” she says.

At Ermine Lovell Real Estate in Falmouth, Manager/Broker Katie Collette says the timing for rentals varies, with some folks booking as early as the previous summer and others waiting to firm up plans, often around children’s summer camps on the Cape. Regardless of timing, bookings remain strong. “Every year it continues to grow,” Collette says.

“What we’re seeing now is a lot of generational rentals,” she says, where a family rents a house large enough to accommodate parents, grandparents and grown children with their own families.

“Large homes, and homes on the beach, those tend to go the fastest,” she says. But since the firm is always getting new listings, “It’s not too late.”