8 Remote-Friendly Companies That Will Pay You To Take a Vacation

More and more companies are jumping on the work-from-home bandwagon, which of course has both pros and cons to it. However, some employers are taking benefits a step further and motivating workers to use their PTO through a nontraditional yet efficient strategy: paying for their vacation.

From an annual travel stipend to moving the office to a tropical destination, these remote-friendly companies are giving employees an extra incentive to get away by helping to finance it. Even when you’re entitled to it, the “work guilt” can lead to not taking time off, resulting in unused days—and these companies are trying to prevent that at all costs (which, in this case, means paying for vacation).

With the help of career site Flexjobs, we found eight companies in alphabetical order that hire remote workers and help them take the time off they deserve.

The online marketplace that’s known for its rental listings and experiences is helping employees practice what they preach. Those who work at Airbnb get annual travel and experiences credit to take a break from work while exploring the bookings the company has to offer.

In addition to promoting Work from Home Wednesday and a generous paid vacation package, online marketplace Bonanza also offers up a tropical getaway in February for all employees (and their families). As part of “Freedom February,” Bonanza moves their office to what they call a “tropical paradise” for a few weeks and invites everyone to join.

The note taking app Evernote encourages employees around the globe to take a vacation by offering up a $1,000 annual travel stipend. The company believes that this is a great way to recharge your battery, and we couldn’t agree more.

If you’ve ever tried to find the cheapest flight or hotel for an upcoming trip, Expedia is probably a tool that you’ve used. Of the many benefits that they promote for their employees, remote or not, Expedia offers a leisure travel reimbursement as well as discounts on retail and travel packages on their site.

The financial and investing advice employer picks one employee’s name at a monthly drawing, and whoever is selected has to take a two-week vacation with financial help from the company. The program is called “The Fool’s Errand” and the chosen “Fool” has to completely disconnect from the office during the two-week period, and must take the time within the next month.

With 21 days, sick and safe leave, and 10 holidays, the software service company pushes its employees to take all their vacation time by providing a PAID paid vacation. Yes, that extra “paid” means that they’ll help pay for a chunk of it by providing a $3,000 stipend to spend while you’re away.

As another travel company featured on this list, it’s probably no shock that the perk is a vacation stipend (but nonetheless, still very nice). TripAdvisor offers up a personal travel allowance—likely determined by the amount of years at the company—and offers a starting PTO package of 15 days to use it.

As a major airline, United offers unlimited standby travel and discounted rates on any of its domestic and international routes. So if you’re looking to jet off much more in 2020, this is the employer for you.