NEW YORK – Debbie Wosskow created a way to help travelers avoid hotel costs on their next vacation by swapping their Manhattan apartment for a villa in Zanzibar.

What she hasn’t figured out is how to insure their stuff.

Wosskow, CEO of London-based Love Home Swap, which she describes as “online dating for homes,” said it was easier to find people in 95 countries to post properties on the website and make a trade than to line up coverage in case something goes wrong.

After contacting about two dozen insurers, she’s been able to strike a deal for coverage of residences only in Europe. That means about two-thirds of homeowners will have to arrange their own or go without.

“It’s a nightmare,” she said. “The insurance industry as a whole has been painfully, and I emphasize painfully, slow to react and offer relevant services.”

Startups that help people rent their houses and cars to strangers have proliferated on the Internet, with Wosskow’s firm now listing about 5,500 properties, three times as many as in December. The entrepreneurs behind the companies are finding they have to convince insurers from Warren Buffett’s Berkshire Hathaway to Hiscox they’re worth the risk.

The process was a surprise for Tony Adam, who co-founded Eventup, a service for finding and booking properties for parties and other gatherings. It took only two months for the startup to build and launch its website and three to secure a policy through Lloyd’s of London, he said.

“I thought it would be as simple as going to a site and finding $1 million of coverage and taking care of it,” said Adam who, like other entrepreneurs, declined to disclose his company’s insurance cost.

Part of the challenge is that they’re asking insurers to blend elements of policies that protect personal property with ones tailored toward companies, said Paul Mang, a partner at Razor’s Edge Consulting and the managing director of Avarie Capital, which invests in companies involved in the insurance industry.

There are also generational differences, he said: Startups are advocating an idea of property that tends to appeal more to younger people.

“It’s hard for baby boomers to get their head around this,” said Mang, a former leader within McKinsey & Co.’s property-casualty insurance practice. “Why would anybody rent out their car for $5 an hour?”

The search for Getaround, which helps car owners rent vehicles and counts Yahoo CEO Marissa Mayer among its investors, took more than a year and a shift in business plan. Sam Zaid, the company’s CEO, said he contacted 60 to 80 carriers, calling insurance executives he found on LinkedIn.