7 Factors to Consider if You Plan to Work From Vacation Home

By Amanda Wowk

November 18, 2020

’Tis the season to take your remote work on the road. Recently released data from TripIt revealed that travelers are extending the duration of their upcoming holiday trips and increasingly looking to book vacation rentals for their longer-term stays. While an extended change-of-pace (and place!) might be just what you need to enjoy the remaining months of 2020, WFvH (that is, working from vacation home) requires more research and planning than a quick jaunt to your favorite vacation destination.

If you’re thinking about WFvH, here are seven factors to consider before clicking Book on that vacation rental. 

Time zones 

While some all-remote companies are shifting towards an asynchronous work model, you might still need to sync up with colleagues when you’re WFvH. If that’s the case, one important factor to consider is your time zone. If your organization is based in New York, for example, and you’re planning a month-long remote work getaway to San Diego, your weekly 9 AM team meetings have just switched to a 6 AM start time. (The same applies for the younger members of your family participating in virtual learning.) This shouldn’t hold you back from a month in sunny California per se, but being cognizant of time zone differences and how they’ll impact your day-to-day schedule and deadlines are important considerations before you book. 

How you work best—and if WFvH will accommodate 

If you’ve been working from home since the start of the pandemic, you’ve likely established your remote work routine: where you work (e.g., your dedicated office, dining room table, standing desk in your bedroom, etc.); when you work (e.g., creative work in the morning, emails over lunch, administrative tasks in the afternoon); and how often you work (i.e., learning to set healthy boundaries in an always-on, virtual world). 

If you’re planning to work from vacation home (especially longer term), you’ll want to think through how to make a new (albeit temporary) space work for you. For instance: 

  • Do you need an office with a door, or can you work in an open floor plan with other family members around? 
  • Does your work require quiet for writing or presenting (without interruptions) on video calls? If so, does the vacation rental layout lend to that need?
  • If your kids are doing remote schooling, will they have the space they need in a vacation rental to get their work done, too? 

Getting clear on the next iteration of your remote work needs will help you find a vacation home that works for you. 

Tip: Remember to forward your reservation(s) to TripIt to create a master itinerary for your trip. Then, you can access features like Nearby Places to quickly locate items you need while you’re there or Neighborhood Safety Scores to understand the safety and risk levels of the area(s) where you’re staying.


Remote school. Remote work. Remote internet provider? Another consideration, especially if every member of your family will be relying on Wi-Fi for their respective responsibilities, is if your chosen vacation home supports your connectivity needs. In short, unstable Wi-Fi or internet access is a no-go.

Before booking a vacation home, be sure to read the reviews prior guests have left. Therein lies clues to your WFvH experience. You can also message the host before you book to inquire as to whether the Wi-Fi will support your remote working needs. You might want to ask whether the Wi-Fi reaches every room in the house, for example, and what bandwidth their service supports. A necessary consideration should you have two or more video conferencing calls taking place at once.  

Tools and gadgets you can’t work without

Thinking back to those first few weeks of working remotely, you probably quickly identified the comforts of the office you missed in your home office set-up. Whether that was your ergonomically-designed desk chair, extra monitor (or, a monitor to begin with!), wireless keyboard, or standing desk, there were adjustments you had to make—and gadgets and tools you had to buy—to make working at home sustainable. 

When considering a WFvH set-up, you’re likely going to want all of those comforts on the road, too. If you’re planning a road trip to your destination, you’ll have more flexibility to bring your own supplies along. On the other hand, if you’re planning to fly, you might want to consider shipping the tools and gadgets you need. Alternatively, you could check out an online marketplace for second-hand versions of the larger items you’re leaving at home. That way, your at-home set-up stays intact, you have what you need to work for the duration of your stay, and you’re choosing a sustainable option by giving old gadgets new life.

Expenses and taxes

The allure of working remotely from another country (Barbados! Estonia!) is hard to deny, but there are details to consider before you embark on an international WFvH adventure. Namely, the tax implications of working outside of your home country. The same goes for an extended WFvH in another state. Depending on the length of your stay, some states may require you to file taxes. 

Our advice? Doing your research ahead of time will help you make well-informed financial decisions, such as whether or not to hire an accountant, establish a WFvH budget, and track your expenses, so that when it comes to filing next year’s taxes, you’re prepared—and there’s no unexpected surprises. 

Read The Freelancer’s Guide to Business Travel for more expert tips from veteran freelancers

Maximizing your WFvH spending

If you haven’t dusted off your travel credit card in a while, you might be pleased by some of the new categories available for rewards. For instance, some cards have introduced new categories (such as groceries) or increased the rewards for others (such as meal delivery and ride share programs). Before you start incurring these everyday expenses while working from your vacation home, check with your credit card provider so you can maximize your spending and earn points for future travel and more. 

Taking time off 

Finally, remember to keep the vacation in work from vacation home. While many people are fortunate to work from anywhere, doing so doesn’t replace the need to take a break—including from your screens and your workload. Be sure to schedule (and take!) time off during your trip. Whether it’s to celebrate the holidays, reconnect with family, or simply recharge, your post-WFvH self will thank you for it.