Having the flexibility to take trips while working a full-time job is appealing. In addition to providing ample time off, some employers also offer stipends to cover expenses like flights and hotels as a way to encourage their employees to take time for themselves. The following companies that pay you to travel give their employees benefits options that help them fulfill their travel goals.

Companies That Pay You to Travel

  • TripAdvisor
  • Expedia Group
  • Calendly
  • Anyplace
  • Payhawk


Companies That Pay You to Travel

TripAdvisor operates a reviews platform for hotels, restaurants and other hospitality businesses frequented by travelers. In keeping with the company’s “get out there and see the world” ethos, it provides employees with a suite of benefits that support travel, including the Global Lifestyle Benefit, which gives team members an annual allowance they can spend on travel. The company also offers paid vacation time and employee resource groups that support team members from all over the world. 


Expedia Group is a travel tech company with a platform that enables users to book all aspects of travel, from hotels to flights to experiences. It also partners with travel-adjacent businesses and influencers to curate its travel support ecosystem. Expedia employees enjoy benefits that support travel and other adventures, like travel reimbursement and paid time off for vacations.  

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Calendly makes scheduling technology, offered through a platform that integrates with Zoom and Google Calendar for a seamless booking and meeting experience. Users can integrate their unique Calendly link into their website or email signature to allow clients, colleagues or students to book time at their convenience. Calendly employees receive flexible time off and a $1,000 annual vacation stipend to go anywhere they want.


Anyplace is a real estate tech company that provides fully furnished luxury apartments for remote workers and digital nomads. All apartments come turn-key, with high-speed Wi-Fi, fully equipped workspaces and flexible terms, so that workers can move in on a moment’s notice and move out when their contract ends or the spirit moves them. Anyplace provides a travel stipend and an unlimited vacation policy to employees.


Payhawk is a fintech company that offers a spend management platform for automating business spending. It provides clients with prepaid company cards, which are tracked in real time, to dispense to their employees. Payhawk team members enjoy a corporate travel benefit that allows them to spend a week working from a global Payhawk location, like Amsterdam, Paris or London, with transportation and a spending allowance included.

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