(Bloomberg News) 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, chief executive officer 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 Web site 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 Inc. to Hiscox Ltd. 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.

'Didn't Understand'

"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. "Some brokers didn't understand what we were doing."

Part of the challenge for the startups 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 LLC, which invests in companies involved in the insurance industry.

There are also generational differences. The startups are advocating for an idea of property that tends to appeal more to younger people than older insurance executives, he said.

"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?"

Cold Calls