12 Flexible Companies That Help Pay for Your Vacation

By admin Jun 1, 2023


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Editor’s Note: This story originally appeared on FlexJobs.com.

Are you daydreaming of a sun-soaked beach on a tropical island? Or, maybe your summer vacation dreams are closer to home, like a relaxing staycation or a charming bed-and-breakfast in your city’s historic district.

Whatever your vacation dreams are, finding a job with a company offering paid time off is likely high on your list of priorities. And why wouldn’t it be? Time off work to recharge and unwind is crucial to our well-being.

However, not all employees fully utilize this significant benefit. According to a recent survey from the Pew Research Center, 62{1652eb1ffa4184925f6a63a9c04ea6b421acb7a78117241e7d4325cdca8339fa} of workers consider paid time off an “extremely important” job perk.

However, nearly half of employees aren’t taking their full allotment of vacation time.

So, you have an essential question to incorporate into your job search: How can you ensure you’re making the most of your entitled paid time off while still building a successful career?

One solution could be finding a job with a company that goes the extra mile by not only offering vacation time but actively supporting and even funding your time off.

Supporting Employee Well-Being

Happy young woman on vacation or traveling
Dean Drobot / Shutterstock.com

Employee wellness has moved into the spotlight in recent years. Recognizing the positive impact vacation time can have on employees’ mental and physical health, many companies seek innovative ways to support their teams.

Savvy companies know that encouraging self-care among employees is a win-win situation. Not only does the team feel better, but the company also sees improvements in productivity and lower staff turnover.

As a result, many companies are providing financial incentives to encourage staff to disconnect and recharge.

Keith Spencer, career expert at FlexJobs, comments on this rising trend: “Vacation time is vital to workers’ well-being, yet most people aren’t leveraging the time off they need to recharge. Fortunately, a growing number of companies are recognizing this gap. They’re not just providing paid time off but taking active steps to motivate and support their staff to make the most of it.”

12 Remote Companies That Help Pay for Your Vacation

Happy woman in an airport
Chaay_Tee / Shutterstock.com

Based on FlexJobs’ research, the following list features companies that help pay for, reimburse for, or provide a stipend or bonus for employee vacations.

They’re either currently hiring or have recently hired for fully remote roles.

If you don’t see a job that fits your interests, add the company to your list to watch for future vacancies.

1. Airbnb

Excited woman ready to travel
Prostock-studio / Shutterstock.com

Airbnb employees receive annual travel and experiences credits.

Recent remote job postings:

  • Senior Principal, Tax Policy
  • Senior Staff Engineer — Pricing

2. BambooHR

Man using a traveler's check
LightField Studios / Shutterstock.com

BambooHR employees are offered “paid paid vacation” — a $2,000 annual stipend to use toward travel.

Recent remote job postings:

  • Human Resource Business Partner – Product and Customer Experience
  • Senior Channel Manager, SEO

3. Calendly

Happy couple using laptop and planning travel with credit card rewards
wavebreakmedia / Shutterstock.com

Calendly employees annually receive a $1,000 vacation stipend to put toward hotels, flights, or rental cars.

Recent remote job postings:

  • Senior Product Manager, Sales Systems
  • Product Operations Specialist III

4. Disruptive Advertising

Family at an airport
NicoElNino / Shutterstock.com

Full-time Disruptive Advertising employees are eligible for a vacation bonus after their first anniversary.

Recent remote job postings:

  • Executive Assistant
  • Senior HR Manager

5. Evernote

travel costs
Wollertz / Shutterstock.com

In addition to unlimited vacation days, Evernote employees are provided a $1,000 annual vacation stipend for breaks of five days or more.

Recent remote job postings:

  • Marketing Operations Specialist
  • Social Media Manager

6. Evolve Security

RV
sirtravelalot / Shutterstock.com

Evolve Security employees receive an annual vacation reimbursement for personal travel expenses.

Recent remote job postings:

  • Adjunct Instructor — Cybersecurity
  • Integrated Marketing Manager

7. Expedia

happy couple
sirtravelalot / Shutterstock.com

Expedia employees receive a wellness and travel reimbursement.

Recent remote job postings:

  • Manager, Investor Relations
  • Senior Security Operations Analyst

8. FullContact

Couple taking a selfie with an RV
sirtravelalot / Shutterstock.com

FullContact employees receive an annual “lump sum vacation bonus” and unlimited paid time off.

Recent remote job postings:

  • Partner Manager
  • Analyst — Data Quality and Analytics

9. Philo, Inc.

Woman holding ice cream cones
Krakenimages.com / Shutterstock.com

Philo, Inc. employees receive a $2,000 vacation bonus.

Recent remote job postings:

  • Senior Product Data Scientist
  • Android Software Engineer

10. Thirty Madison

Couple on vacation
Akhenaton Images / Shutterstock.com

Thirty Madison employees receive a $750 annual vacation stipend.

Recent remote job postings:

  • Agent, Care
  • Payroll Coordinator

11. Tripadvisor

People sitting on the beach at sunset
Song_about_summer / Shutterstock.com

Eligible Tripadvisor employees receive a “Global Lifestyle Benefit,” which is an annual allowance that can be used on travel and other areas.

Recent remote job postings:

  • CRM Manager
  • SEO Senior Strategist

12. United Airlines

Happy family in the airport
Robert Kneschke / Shutterstock.com

United Airlines employees receive unlimited standby travel and discounted rates on airfare.

Recent remote job postings:

  • Senior Engineer — Flight Operations
  • Customer Service Representative

You Don’t Have to Put Life on Hold for a New Job

Job candidate in an interview
fizkes / Shutterstock.com

It’s hard not to feel anxious about future vacation plans when you’re in the middle of a round of interviews. However, according to the career experts at FlexJobs, there’s no need to put your well-deserved time off on hold.

If a company is genuinely committed to promoting work-life balance through paid time off and other benefits, you should feel confident discussing your upcoming vacation plans during an interview.

Consider these companies, and then commit to prioritizing your wellness. One of the best ways to do that is by working for a company that supports you in every way. Fortunately, that’s getting easier than ever before.

Spencer notes, “We hope this list helps remote candidates connect to careers at these companies and inspires other employers to embrace similar benefits for their workforces.”

Recharge and Thrive With a Better Work-Life Balance

happy woman worker using laptop and excited
fizkes / Shutterstock.com

Finding a healthier work-life balance should be a top priority for every job seeker. While paid vacation doesn’t guarantee you’ll find it, it’s certainly a step in the right direction.



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