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The Largest Vacation Rental Website You've Never Heard Of

Tripping.com has more listings than Airbnb and other sites combined. So...why haven't you used it yet?
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When looking for a vacation rental, perhaps you do a general web search and comparison shop by clicking around on a variety of sites such as HomeAway, Airbnb, TripAdvisor, and VRBO. But what if you could go to just one site and have access to more vacation rentals than all of those sites combined? Enter Tripping.com, which does just that.

Through partnerships with dozens of vacation rental sites (including HomeAway, TripAdvisor/Flipkey, VRBO, and Booking.com, to name a few), Tripping.com is able to aggregate those listings, so you don't have to jump around between sites when searching for homes. The site also allows you to compare prices, and you can often book directly. “We are the first meta-search site for vacation rentals,” explains Jen O’Neal, co-founder and CEO of Tripping.com. With eight million rental listings in 150,000 destinations worldwide, it is also the largest vacation rental search engine out there (for comparison, Airbnb has roughly 2 million listings).

Although Tripping.com was launched in 2010 by O’Neal and Jeff Manheimer, both veterans of the online travel industry, it wasn’t until 2011 that the site debuted in its current incarnation. “We noticed that when looking for vacation rentals, the same rental would be on multiple sites at different prices, and we realized there was a need for a different search model,” says O’Neal. “Kayak and other travel verticals had already created meta-search sites for flights and hotels, and we saw so clearly that it would work for vacation rentals.”

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It took a little while for the industry to see their vision, largely because vacation rentals were not as popular several years ago as they are now, according to VRM Intel, an industry resource for vacation rental managers. Turns out, it was only a matter of time. VRM Intel research shows that as the demand for vacation rentals grew, venture capitalists began to invest in larger amounts. From 2011 to 2015, funding for vacation rental tech companies went from 1.54 million to 2.19 billion. In the U.S. alone, the percentage of adults who have stayed in a vacation rental has quadrupled from eight percent in 2011 to 32 percent in 2015.

“The market caught up with us in a big way,” says O’Neal, and it’s still on the upswing. Estimates show that the current $100 billion dollar vacation rental market is on track to grow to nearly $170 billion by 2019 and to $285 billion by 2025. This means there will be even more travelers looking for a seamless way to search for the best vacation properties at the lowest prices.

And Tripping.com certainly makes it easy. All you have to do is type in your destination and dates and let the site cull through its curated data. To narrow your results, you can filter your search by selecting a price range, number of people who will be staying, and your desired amenities such as a pool, balcony, Internet, and air conditioning—a pretty standard process. The site will then display all of the properties available with their prices on various sites listed side-by-side. You also have the option to add hotels into your search simply by clicking on tags for Hotels.com, Hilton, GoSeek, Expedia, TripAdvisor, and Priceline. Those results will pop up in separate windows when the search is complete.

While the user experience is intuitive, you are forced to wait a bit as Tripping.com digs into its data—a minor but real annoyance. For instance, once your search results are visible, you can’t simply click on a property and preview it in detail. Instead, when you click on a listing, you’re taken through to a partner site, and the loading up of that site takes a little time. Still, the whole process is much faster than having to locate each of those rentals at separates sites on your own. And when it comes down to it, the easy price comparison is key.

Also key? You might save money. The company estimates that travelers save approximately 18 percent by using Tripping.com, which is the average price difference for rental properties on multiple sites. “Being able to offer transparency for travelers and save them money and time, that’s our mission,” says O’Neal.