Evelyn Higgins is looking for an apartment for her family of three but hasn’t come up with anything yet. Emily Sobel was hoping for a year-round house but is renting a single room instead. Caylin Kennedy needs a room for her summer job but has begun making other plans. Chelsea Payne rejected a contract on the Island because she couldn’t find a house.

Stories of fruitless housing searches and expiring leases are not new on the Island, where for many the Vineyard shuffle — a twice-annual move from summer rental to off-season housing and back — has reliably marked the changing of the seasons for decades. But this year, the perennial challenge of finding season-long summer housing has reached new heights as the confluence of a lingering pandemic, a record-shattering real estate market and most recently, an explosion of pricey short-term and vacation rentals, turn what has long been a bad situation into a near crisis for many.

“I think it’s just the pinnacle of what has been building up for a really, really long time,” said Ms. Sobel. “I think this was always coming, and that everyone has seen this coming.”

Conversations with renters, business owners and affordable housing experts this week painted a troubling portrait of an Island in crisis, as the challenge of securing affordable housing poses fresh threats to the Island community and infrastructure at every level.

At the Martha’s Vineyard Hospital, chief financial officer Ed Olivier said the hospital has struggled to find housing this summer for about 160 emergency room and ancillary physicians who return each year to staff the hospital through the busy summer months.

Typically, the hospital provides housing from 58 properties — most of which are rented — to its seasonal employees, but a number of those houses have recently been sold or otherwise taken off the market, he said.

“We’ve lost more than normal, in a typical year, and we have not been able to pick up as many places,” said Mr. Olivier. For the hospital solutions have included housing summer workers in the homes of full-time employees or converting administrative spaces in hospital-owned housing into bedrooms.

Islanders from all walks of life — whether in search of year-round situations or season-long leases — agreed the search has been more challenging than ever.

“It’s very been very difficult overall because when you think you find a place that’s really good, they throw you a curveball,” said Evelyn Higgins, an Islander currently living in a studio apartment with her fiance. Ms. Higgins, who is pregnant with her first child, said she’s been searching for more stable year-round housing for her growing family since the fall. She is due in two weeks.

“We just want something that’s going to be a better environment for the three of us,” she said.

Ms. Sobel, an Islander and owner of Dock Street Coffee Shop, has been renting both long-term and seasonally since moving back to the Vineyard in 2016. After searching for a year-round two or four-bedroom this winter, she has settled for now on a room in a shared house. David Ferguson, a single father who shares custody of his young son, has looked for family-suitable housing for nearly a year but has come up short.

“I think it would be easier if I was a single person but having my son . . . it makes it far more complicated,” he said. “This year I’ve just given up because there’s nothing out there.”

A Facebook group devoted to long-term housing inquiries, called MV Long-Term Housing Rentals was flooded with a staggering volume of requests, far outweighing available inventory.

David Vigneault, executive director of the Dukes County Regional Housing Authority, has 270 households on an ever-growing wait list.

A housing needs assessment conducted by the Martha’s Vineyard Commission in 2020 found year-round housing stock has decreased by 603 units — or 8.3 per cent — over the past two decades. Seasonal vacation homes, on the other hand, have increased by 15.4 per cent, or 1,428 units in the same period.

As the market booms, rental prices have climbed too. Average monthly rents on the Island have risen from $1,180 in 2010 to $1,459 in 2020, according to the assessment, while a growing trend of renter displacement due to the sale of homes has exacerbated the problem, with more people entering an increasingly competitive market.

Many renters, including Ms. Higgins, said they’ve struggled to afford the few rentals still available on the market.

Others are simply not finding anything at all.

Caylin Kennedy, who works as a summer traffic officer in Edgartown, said with no leads so far, she has begun looking for alternative summer jobs in her hometown of Leominster. “I’ve searched high and low for everything . . . I love the Island and I loved the traffic officer position . . . [but I’m] weighing the costs and benefits,” she said. Chelsea Payne, a physical therapist from Cambridge who specializes in home health, has canceled her plans for a three-month contract on the Island this summer. “I did not have any leads at all for housing — not even an offer that was out of budget, just no offers at all,” she said.

The affordable housing crisis continues to take a toll on Island businesses too.

Doug Abdelnour, owner of Nancy’s Restaurant and Noman’s in Oak Bluffs, said the lack of housing has already dealt a blow to his summer staffing, which is down almost 50 per cent this year as long-time employees decline to return.

“I’m losing some like really key people who have been with us for a long time . . . There’s not one department that we have solidified this year,” said Mr. Abdelnour, speaking of both his restaurants.

In past years, Mr. Abdelnour has provided housing for 25 summer employees. This year, he has begun putting people in his own home. But that’s hardly a solution, he said.

“It’s so bad now that we’ve stopped from saying we need to find ways to rent more houses because it’s just not even a possibility,” Mr. Abdelnour said. “Most of our meetings with our management team over the last couple of weeks have all been, how do we downsize, how do we limit the menu . . . how do we make this work?”

At Coast Guard station Menemsha, Justin Longval said the agency can provide up to seven residences for its employees with families, but those without partners or children have to find housing themselves. Of the 23 guards at the station, he said four have chosen to live off-Island and commute to work instead.

At Dock Street, Ms. Sobel said she hoped to provide employee housing in the future, but that plan remains far off. “Right now, I’m searching for housing for myself,” she said.

“We’ve been feeling it for years but this year is magnified,” Mr. Abdelnour said. “It won’t be long before this trickle down effect of poor service, not just at a coffee shop and a restaurant, starts to happen.”

Mr. Olivier said as of Thursday, he’d found housing for all incoming hospital employees but one. But he said the problem looms large.

“My sense is that this will probably get worse over time until there’s a way to create density in housing on the Island so that things can be more affordable,” said Mr. Olivier. “We can’t run half an ER for the summer. That would not be fulfilling our mission, so we don’t do that,” he said. “We would just have to figure out a way to bring in the people who we need.”