15 Companies That Offer Remote Positions — and Help Pay for Your Vacation

A traveling couple takes a selfie in a plaza.
Drazen Zigic / Shutterstock.com

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

Many employers, including Delta and Expedia, are recognizing how valuable time off is for employee wellness, engagement, and productivity, and some are even helping fund that time away.

A growing number of companies offer travel stipends, vacation funds, discounts, credits, and other financial perks to encourage employees to take the breaks they deserve.

In this article, we highlight 15 companies that hire for remote jobs with travel benefits that can help fund your time off. We also share jobs where travel is part of the day-to-day work.

Each of the following 15 companies hires for remote jobs and work-from-anywhere roles with travel perks and corporate vacation packages.

1. BambooHR

As an employer, BambooHR is a human resources-focused computer software company that offers an affordable, intuitive, cloud-based system for managing essential employee information.

As an employer, BambooHR encourages team members to find purpose beyond software and salary, incentivizing talented applicants to do their best work and make a difference while having fun along the way.

Employee travel benefits: Eligible employees are offered “paid paid” vacation.

2. Calendly

Calendly is a scheduling automation platform helping businesses and individuals schedule meetings so they can work on “what’s really important.”

As an employer, Calendly supports a flexible workplace and shapes its culture around curiosity, creativity, collaboration, and learning from both success and failure while ensuring every voice is heard and always starting with a focus on caring for its people.

Employee travel benefits: Eligible employees receive a quarterly stipend to spend on vacation or other areas.

3. Delta

Delta is a global airline serving hundreds of destinations worldwide while supporting employees through comprehensive travel, wellness, financial, and family-focused benefits. As an employer, Delta promotes career growth, employee well-being, and a people-first culture through learning opportunities, flexible support programs, and travel-focused perks for eligible workers.

Employee travel benefits: Eligible employees receive unlimited standby travel privileges, airfare discounts, Delta Vacations discounts, and access to additional travel and commuter savings.

4. Disruptive Advertising

Disruptive Advertising develops and executes digital marketing strategies to accomplish its mission of helping companies grow.

Disruptive Advertising strives to cultivate a culture based on its values of caring for each other, using a growth mindset, having “radical candor,” and taking responsibility and ownership.

Employee travel benefits: Employees are eligible for a vacation bonus.

5. Expedia

Expedia is an award-winning, web-based travel service available in nearly 40 languages that has served clients in more than 60 countries.

The company says it embraces diversity and doesn’t believe in performance ratings. Instead, the company promotes ongoing communication and equips its team with “tools to outperform.”

Employee travel benefits: Eligible employees are provided a wellness and travel reimbursement.

6. Hopper

Hopper is an accredited, mobile-only travel agency using big data to analyze and predict airfare and accommodations.

As an employer, Hopper operates in a fully remote environment and deliberately designs its culture as an operating system to accelerate growth, foster autonomy, and create a strong sense of belonging, enabling new team members to integrate quickly and contribute meaningfully from day one.

Employee travel benefits: Eligible employees get $200 of Carrot Cash per year to use toward a trip in the app.

7. Kasa Living

Kasa Living is a hospitality company that offers luxurious, home-like apartments in over 35 cities across the United States.

As an employer, Kasa Living highlights flexibility as a core value, offering health coverage, a flexible paid time off (PTO) policy, and other perks to support its team members’ well-being and work-life balance.

Employee travel benefits: Employees are eligible for up to $2,000 in annual lodging credits at any Kasa location.

8. Kindred Concepts, Inc.

Kindred Concepts, Inc. is a members-only home-swapping network that enables travelers to avoid the high costs of hotels and vacation rentals by exchanging homes with people they trust.

As an employer, Kindred Concepts offers flexibility that encourages travel and adventure while fostering a vibrant, inclusive culture that celebrates diversity.

Employee travel benefits: Eligible workers receive a quarterly $1,000 travel stipend.

9. MNTN – Mountain

MNTN (Mountain.com) is a direct-response marketing startup offering solutions for brands looking to use the power of television to build site visits, drive revenue, and increase measurable conversions.

As an employer, MNTN fosters a culture of ownership, impact, and enthusiasm, supported by generous benefits like 100% healthcare coverage, coaching and therapy access, and monthly three-day weekends.

Employee travel benefits: Eligible employees receive a $2,000 annual vacation stipend.

10. Olark

Olark offers a live chat platform used by companies to drive sales, capture leads, support customers, and collect real-time feedback with customizable, targeted chat features.

As an employer, Olark fosters a flexible, people-first culture guided by its C.H.A.M.P.S. philosophy, emphasizing empathy, collaboration, transparency, and sustainable work while offering benefits like coworking and internet stipends, medical coverage, paid parental leave, and more.

Employee travel benefits: Workers are eligible for a $1,000 bonus if they take at least five consecutive days off.

11. Philo, Inc.

Philo provides a package of top-rated television channels for $25, where customers can watch live TV, save unlimited shows to watch later, or browse a large library of content available on demand.

As an employer, Philo empowers its team of “Philons” to tackle inspiring challenges and innovate within a people-first, collaborative culture that values diversity, inclusion, transparency, and shared success.

Employee travel benefits: Eligible employees receive a $2,000 vacation bonus.

12. Qualtrics

Qualtrics helps businesses worldwide assess the quality of their customers, products, employees, and brands through its software platform, Qualtrics Experience Management (XM).

As an employer, Qualtrics embraces a “work hard, play harder” culture that promotes work-life balance, growth opportunities, and unique perks like office pubs while fostering global connection through video meetings and an internal social network.

Employee travel benefits: Eligible employees are provided an annual bonus for an experience of their choosing.

13. Tripadvisor

Tripadvisor is an award-winning network for travel information covering inns, motels, hotels, restaurants, and attractions, and offering free travel guides, honest reviews, worldwide rental listings, low airfare, and user-generated forums.

As an employer, Tripadvisor supports personal health and well-being through a benefits package that includes medical coverage, paid time off, summer Fridays, educational assistance, fitness reimbursements, and more.

Employee travel benefits: Eligible employees receive a “Global Lifestyle Benefit,” an annual allowance that can be used on travel and other areas.

14. United Airlines

United Airlines operates over 4,500 flights every day to more than 335 airports on five continents.

As an employer, United Airlines fosters a diverse and inclusive work environment recognized by the Human Rights Campaign while offering eligible employees health, financial, social, and professional benefits, along with travel perks.

Employee travel benefits: Eligible employees get unlimited standby travel and discounted rates on airfare.

15. VERB Interactive

VERB Interactive is a Canada-based digital marketing agency on a mission to create solutions for clients within the hospitality and travel industry.

As an employer, VERB Interactive supports work-life balance through flexible arrangements, including alternative schedules and remote options, while offering benefits such as health and dental coverage, professional development, transit and fitness discounts, and free snacks and drinks.

Employee travel benefits: Workers are eligible for a $750 annual travel credit when they travel and stay with one of VERB’s partners.

Jobs Where Travel Is the Work

If you’d rather not wait for PTO to travel, some roles build travel directly into the job. These travel jobs can offer consistent opportunities to explore new places while getting paid, often with added perks like stipends, housing support, or travel reimbursements.

Here are some common jobs with the best travel perks built into the role:

  • Consulting: Many consultants travel to meet clients, attend on-site meetings, or support projects across different locations, especially in industries like business, tech, and healthcare.
  • Event planning: Event professionals often travel to plan and execute conferences, corporate events, or weddings, working on-site in different locations throughout the year.
  • Flight attendant: Flight attendants travel frequently as part of their job and often receive additional perks like free or discounted flights, flexible scheduling, and opportunities for personal travel between routes.
  • Healthcare: Travel nurses and allied health professionals take short-term assignments in different cities or regions, often with housing stipends, licensing support, and relocation assistance included.
  • Hospitality: Roles in hospitality, including cruise lines and resort operations, allow employees to live and work in destination locations while gaining experience in customer service, entertainment, or operations.
  • Journalism and photography: Journalists, especially those covering travel, culture, or international news, may travel frequently to report stories, conduct interviews, and photograph events on location.
  • Sales: Sales professionals in field roles may travel regularly to meet clients, attend conferences, or manage territories, with expenses like transportation and lodging typically covered.
  • Travel writing and content creation: Content-focused roles can involve traveling to different destinations to create articles, guides, or social media content, often on assignment or through brand partnerships.

You can also explore digital nomad-friendly roles, such as software development, marketing, writing, and design. These are some of the best jobs with travel perks that don’t necessarily require travel but allow you to work from anywhere, giving you the flexibility to travel on your own terms.

 

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