Skip to main content

Tripping books $16M for its vacation search engine

Image Credit: Tripping.com

Vacation rental startup Tripping announced today that it took in a $16 million investment from multiple investors, including Singapore-based Enspire Capital and Steadfast Venture Capital in New York.

Company founder and CEO Jen O’Neal describes the company as “the first vacation rental search engine” and says Tripping has multiple partnerships with stay-booking websites worldwide, offering everything from budget rentals to luxury mansions.

If you ever hoped to spend a night in a castle in Scotland, Tripping has you covered. The smaller regional partners also let you choose more modest stays for much less.

Tripping says it has over five million listings in over 100,000 cities with HomeAway, VRBO, and FlipKey, among other listing sites. The service sorts out everything from location and rates to amenities like WiFi and AC for the home and room rentals.


June 5th: The AI Audit in NYC

Join us next week in NYC to engage with top executive leaders, delving into strategies for auditing AI models to ensure fairness, optimal performance, and ethical compliance across diverse organizations. Secure your attendance for this exclusive invite-only event.


“We offer consumers just what makes sense,” O’Neal told VentureBeat.

Unlike Airbnb, Tripping serves as a a search engine and does not get involved in rental management. Its partners take care of that part of the deal, and Tripping takes a share of the booking. Each partner gets charged a different rate, “so that the deal works for everyone,” the CEO explained.

Tripping says it’s raised a total of “just over $21 million.”

The company says this new capital will be used on growth and international expansion.