17 companies that hire remote workers and offer paid vacation perks

From unlimited vacation time to travel stipends, these companies are helping U.S. workers get some much needed relaxation on the company’s dime.

Backyard vacation plans — Image: Aleutie/Getty Images/iStockphoto

American workers, it’s commonly said and statistically cited, don’t take vacations, and when they do they often feel guilty about it. As we come out of the COVID-19 pandemic, FlexJobs said, “many employees find themselves taking very few vacation days,” which only adds to the stress piled on during the past year.

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FlexJobs wants those looking for a new career to know that the no-vacation normal doesn’t have to continue, at least for those working at one of the 17 companies it included in a list of businesses that hire remote and flexible positions and also help foot the bill for travel and time off.

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These companies, FlexJobs noted, aren’t the only ones that have travel and vacation perks, but they do “provide a great starting point for your search for a better way to work and live.”

AFAR Media: Travel media brand AFAR offers 30 days of vacation as well as a $2,000 stipend for full-time employees.
Airbnb: Employees of this mega-popular hospitality marketplace receive annual travel and expense credits, as well as paid time off for volunteering.
BambooHR: Software solutions company BambooHR offers an annual $2,000 worth of what it calls “paid paid vacation” money for employees.
Basecamp: The company behind this project management software gives employees that have worked with it for at least one year the choice of one of 16 paid vacation packages each year, valued at $4,000 – $5,000 each.
Bonanza: This online marketplace offers paid vacation as well as a unique employee wellness strategy it calls “Freedom February,” in which the whole company physically moves to a tropical location for the whole month and gives employees who come (families are invited, too) five bonus vacation days to enjoy the change of venue.
Calendly: Scheduling tool Calendly offers unlimited time off, a $1,000 annual vacation stipend and a “pick your own perk” program that gives employees another $1,000 to “spend on whatever suits you and your family’s needs.”
Evernote: Popular note-taking app Evernote is run by a company that offers unlimited vacation days and a $1,000 yearly vacation stipend, and it often hires freelancers, too.
Expedia: Travel booking site Expedia uses its services to help employees by providing discounts on retail and travel packages, as well as offering travel reimbursements.
FullContact: This business relationship management platform seems to understand internal business relationships too: It offers $7,500 per year for employee travel and mandates that employees on vacation cannot work.
Motley Fool: The investment advice website Motley Fool offers a surprise vacation perk called “Fool’s Errand,” in which one employee’s name is drawn from a hat monthly and given money toward a two-week vacation, with two caveats: No contact with the company and the trip has to be taken before the next monthly meeting.
Moz: SEO platform Moz offers 12 days of PTO, seven sick leave days, 10 paid holidays and a $3,000 annual vacation reimbursement plan for its employees.
PulsePoint: This healthcare marketing and technology company offers paid vacations and company holidays, paid birthdays off and a $500 annual travel reimbursement.
Thirty Madison: Telemedicine company Thirty Madison has several employee perks, as well as an unlimited vacation policy and vacation stipend.
Travelzoo: Up to $1,500 worth of travel plans and packages found on this website are financed by the company, along with three extra PTO days when employees use the benefit to book a trip.
TripAdvisor: Travel reimbursements from TripAdvisor start at $250, but increase depending on how long employees have been at the company. Discounts of TripAdvisor packages are available to employees, too.
United Airlines: Discounted tickets and unlimited standby travel are available for employees of UA. That may not seem like a lot, but airfare discounts when working for an airline can be pretty substantial.
Yesware: Email services company Yesware offers five-year anniversary trip stipends that, while no amount is listed, FlexJobs describes as “large.”