“Among vacation-rental homes, Florida's market is among the nation's most affordable holiday housing options, according to Tripping.com, a vacation-rental search engine. Florida accounts for the six most affordable vacation-rental destinations for the holiday, including Kissimmee, Orlando and Four Corners. Kissimmee's the most affordable, according to Tripping, costing an average room rate of $36.84 for the holiday weekend.”
“Historically the way this would work is you’d find a vacation rental online, you’d email the host, and you’d show up with a check in hand,” says Tripping founder and CEO Jen O’Neal. “Now you can do all of that online, but on average a traveler will go to at least five sites to book a vacation home.”
Founded in 2010, Tripping.com claims to be the world’s largest vacation home rental site and boasts of having over five million listings spanning 100,000 destinations worldwide. Best described as a meta-search engine, the site pulls in listings from partner sites including HomeAway, VRBO, TripAdvisor, Booking.com and dozens more, providing users a single platform to find vacation properties they may wish to rent.
Tripping is an aggregator of vacation rentals listed across different sites, meaning that listings on FlipKey, TripAdvisor, Booking.com, Roomorama, HouseTrip and more all show up on the site. Tripping allows users to search listings by way of map, which is helpful for those looking to stay in an immediate area. The stock to choose from is by no means limited: the site has over 11,000 listings in the New York City area.
Jen O’Neil, CEO of Tripping.com, which aggregates vacation-rental homes listings from HomeAway, Flipkey and others, is predicting cash bonanzas for locals. [...] “We think it will go to $10,000 a night for a luxury property in Palo Alto or Santa Clara,” she said. “Levi’s Stadium is a new venue, so people are really excited about it.”
"As of Monday, the average price of home rentals for the first weekend, April 10-12, was $669 a night, according to data analyzed by home rental site Tripping.com. That's down 16% compared with this time last year because so many local homeowners wanted to get their piece of the lavish festival spending."
"I know first-hand the frustration a vacationer experiences trying to book a vacation home – it can take days – and it was a question my guest on this episode posed to me. I’m usually the one asking the questions but Jen O’Neal, the founder of Tripping used my response to explain why she launched the company."