Home- and Car-Sharing Sites Struggle to Get Insurance

Entrepreneur Debbie Wosskow created a website she describes as “online dating for homes.” Through her London-based Love Home Swap, a couple in Manhattan can swap their classic-six prewar apartment for a villa in Zanzibar for a week. For Wosskow, finding more than 5,000 property owners in 95 countries willing to hand strangers their house keys has proven easier than getting an insurance company to write her a policy.

After contacting about two dozen insurers, Wosskow struck a deal for coverage starting in September—but only for properties in Europe. The policy, underwritten by Hiscox, will protect against property damage and last-minute trip cancellations. That means about two-thirds of homeowners have to arrange their own or go without. “It’s a nightmare,” Wosskow says. “The insurance industry as a whole has been painfully, and I emphasize painfully, slow to react and offer relevant services.”