Tripping: What You Should Know About a Leading Platform for Vacation Homes

June 18, 2014

5:30 pm

Traveling is one of the world’s favorite past times. You can catch a flight to anywhere in the world and have the opportunity to experience another culture within 10 hours of leaving home. However, one of the biggest challenges to planning a trip is finding a reasonably priced place to stay.

Tripping is now a leading platform for vacation homes and short term rentals, but the first version of the startup was actually a social travel site.

To give you some history, Tripping was growing very fast – they had users in 175 countries in a month – but it’s mission quickly changed because the company wasn’t generating much revenue. With the need for a better business model, the team left the office and took a retreat to Lake Tahoe. With the need for a better business model, the team left the office and took a retreat to go camping. Tripping CEO Jen O’Neal said the research for that trip is what triggered the new version of her company.

“We were trying to find a place and we were looking at a number of sites at once and it just took a ton of time,” says O’Neal.

How Does Tripping Work?

According to a press release, “The site offers over 1 million properties across 50,000 cities worldwide, curated from over a dozen top travel rental sites including HomeAway,, Wimdu, Interhome, HouseTrip, Flipkey and more.” Here’s what first time users should know:

  • It’s kind of like Kayak for vacation rentals: The site partners with large travel sites and O’Neal says they “pull all of their listings into tripping.” No one was using meta-search for the vacation market and O’Neal saw this as an opportunity.
  • It’s Easy to Use: I took a look at Tripping and it is very easy to use: you enter where you want to go – add a check in and check out date and click search.
  • Search and Find what you Need: Users do a search and they’ll “find you vacation homes from all of those sites in a single place,” says O’Neal.

The Vacation Homes Market is Growing

With more than $100 billion dollars in the vacation rental market in the U.S. and Europe, the market is massive. Tripping is targeting four different markets: 20-something professionals, families (usually parents in their early 40’s with kids), retirees and college students.

“We worked with students recently who wanted to go to Mexico for Spring Break. They realized they could have either rented a really nice vacation home and split it among ten people and that would be cheaper if they all went to a hotel and got five rooms,” says O’Neal.

Tripping in the Future

If we look at some of the signs around us, there is definitely a future for Tripping. Airbnb received a billion dollar valuation and O’Neal says that speaks to the excitement around the industry.

Additionally, in late May, Tripping secured Series A funding – participants in the round included Recruit Holdings, RGIP Fund, Quest Venture Partners, former Expedia CEO Erik Blanchford, Qunar founder Fritz Demopoulos, NFL athlete Shawntae Spencer, and other notable investors in Europe and Silicon Valley.

O’Neal says everyone on the team has a voice – even their intern from Australia. However, she has found an amazing partnership with COO Jeff Manheimer, Tripping’s COO.

“Jeff’s entire background is travel, whereas mine was technology,” said O’Neal of her Co-Founder who ran the distribution between Hyatt and Expedia. “We’re really good compliments, he know the travel world really well and I know the tech world really well.”


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Amanda Quick is a tech/startup reporter covering young entrepreneurs for Tech Cocktail. She's also interested in covering apps, emerging technology, IoT and beauty & wellness. Amanda is currently in grad school at Syracuse University studying Information Management. In the past she has interned at NBC Sports, NBC Olympics, Brand-Yourself, and the Times Leader Newspaper as well as worked at WWNY-TV and the StartFast Venture Accelerator in Upstate New York. Amanda is originally from Kansas City, MO but has also lived in Canton, MA and Scranton, PA. To learn more you can visit Like Amanda on Facebook and follow her on Twitter.

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