14 Flexible Companies That Help Pay for Your Vacation 
It’s been commonly reported that Americans don’t take the majority of their allotted vacation time. Case in point: during 2019, only 28% of Americans reported that they planned to max out their vacation days. Whether it’s due to an inability (real or perceived) to take time off, a lack of support from management, or a shortage of funds, many employees find themselves taking very few vacation days.
Not only that, but the U.S. is far behind other countries in the amount of vacation allotted. CNBC reported on Statista research that shows just how lacking U.S. vacation policies are. “A total of more than 30 days of vacation time allotted to workers in France, Germany, Spain and the United Kingdom stands in stark contrast to the 10 public holidays in the U.S., which are not guaranteed to come with pay,” says the article.
However, there are some forward-thinking companies that are seeking to help workers take the time off they deserve, and even financially support much-needed trips. While offering unlimited vacation days is quickly becoming commonplace, some companies offer to pay for employees’ vacations as well. This can be a great recruiting and retention tool for employers. After all, the desire to travel was one of the top reasons reported in a FlexJobs survey for why people seek out flexible jobs.
FlexJobs has identified 14 remote-friendly companies that pay for their employees’ vacations. These companies can provide a great starting point for your search for a better way to work and live.
14 Flexible Companies That Help Pay for Your Vacation
AFAR Media is a travel media brand that seeks to inspire global travel. The company has a magazine, along with a website that features travel guides and articles. According to a blog post posted by the company, full-time employees receive 30 days of vacation time and a $2,000 stipend to encourage them to travel to new places.
Airbnb was established in 2008 as an online hospitality marketplace for hosts and travelers to connect. Airbnb features listings for homes, rooms for rent, villas, boutique hotels, and more. It has served thousands of people through its 2 million worldwide listings. Employees receive annual travel and expenses credits.
BambooHR is an HR software solutions company that seeks to help companies move beyond spreadsheets. It offers software to help with applicant tracking, employee onboarding, time-off management, employee database, and more. Located in Lindon, Utah, the company has hired for part-time and remote jobs in the area. BambooHR offers employees what they call “paid paid vacation“—$2,000 each year to travel as they please.
Basecamp, founded in 1999, is the creator of a popular project management tool of the same name. The distributed company has 50 employees working across 32 cities. According to Business Insider, employees who have worked with the company for one year or more get to choose from 16 different paid vacation packages each year. These trips are valued at $4,000-$5,000 each.
Since its establishment in 2008, this online marketplace has been on a mission to empower entrepreneurs in building “a sustainable business based on repeat customers.” During “Freedom February,” the ecommerce company physically moves its office to a tropical location for the month and gives employees five bonus days off to enjoy the vacation.
Evernote is an all-encompassing app that allows users to capture, organize, and share notes in one place. Links, tables, audio messages, and more can be included in each note. Evernote is located in Mountain View, California, and has offered freelance jobs in the past. The company offers employees unlimited vacation days and a $1,000 yearly vacation stipend.
As a well-known travel booking site, Expedia has served clients in more than 60 countries worldwide. Users of the site can book flights, hotels, rental cars, cruises, and even activities. Employees of the company receive a travel reimbursement, with ranges depending on tenure. They also receive discounts on retail and travel packages purchased through the site.
Another company that pays for your vacation, FullContact is a platform that helps businesses and individuals develop and maintain business relationships. It helps in the areas of identity resolution, contact management, profile enrichment, audience insights and development, fraud prevention, and customer care. FullContact provides $7,500 per year for employees to travel—and it’s required that they don’t work while on vacation!
Motley Fool seeks to “make the world smarter, happier, and richer” through its business and investing advice. In addition to offering unlimited vacation time, the company also has a “Fool’s Errand” program where one employee’s name is drawn from a hat every month and awarded “a decent chunk of money” towards a two-week vacation. The lucky winner has to take the trip before the next monthly meeting and is asked for no contact during their travels to ensure the ultimate in relaxation.
Moz is a software as a service (SaaS) company that develops software for inbound marketing, hosts vibrant communities of online marketers, and provides APIs for link data and social influence. The rundown of what Moz employees receive for vacation is: 21 days paid time off per year, seven days of sick leave, 10 paid holidays, and $3,000 per year vacation expense reimbursement.
Travelzoo is a commerce site in business since 1998. It publishes travel deals from over 2,000 entertainment, travel, and local companies to an audience of 28 million members across the world. It also offers exclusive deals and rates to members who join the site. According to Glassdoor, employees of Travelzoo are offered a “$1,500 stipend and three extra days of PTO to ‘book a hotel stay, vacation package, cruise, or flight offer that we negotiate on behalf of our 28 million members worldwide,’ according to Michael Stitt, President of Travelzoo North America.”
As the world’s largest travel site, TripAdvisor serves more than 350 million users monthly. Users can book flights, hotels, vacation rentals, restaurants, and more. The site boasts a large database of user reviews to help customers make the right travel choices for their needs. As a company, TripAdvisor offers a travel reimbursement of $250 or more, depending on how long an employee has worked at the company. It also offers discounts on packages offered through the website.
Founded in 1926, United Airlines now hosts 4,500 flights every day to more than 335 airports on five continents. As one of the largest airlines in the world, United Airlines seeks to be an inclusive employer and was even named one of the “World’s Most Admired Companies” by Fortune magazine. The company offers discounted airline tickets and unlimited standby travel on any United flight to employees.
Founded in 2010, Yesware is a technology company that provides email services for salespeople. Core features of the company’s product include campaigns, email tracking, a LinkedIn sales navigator, reporting and analytics, Salesforce integration, and templates. The Boston-based tech company offers employees a large travel stipend to fund a dream trip when they celebrate their five-year anniversary at the company.
Advance Your Career at a Flexible Company
If you’re among the majority of Americans who don’t take all of their vacation time, finding a company that encourages work-life balance and time away from the desk is key. FlexJobs has flexible companies and jobs that can provide the work flexibility you’re needing. Check out our listings, which are updated daily!
Photo Credit: bigstockphoto.com
Photo Credit: bigstockphoto.com
A version of this article was originally published on June 25, 2018 and previously updated July 25, 2019.
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Rachel Jay, FlexJobs Editor and Writer
Rachel Jay is a Content Specialist for the award-winning site FlexJobs. She has worked remotely full time since 2012 and believes strongly in the benefits of remote work. With years of experience as an editor, she strives to help make…Read More >
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