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17 Jun 2022
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The verdict is in. Remote work is here to stay! For a great many of us, working remotely from home has become the new norm, and office work has become a near-forgotten thing of the past. With the rise of remote work has also come the exciting concept of “workcations.” The idea is simple; combine your remote work life with a fun vacation. 

If you work remotely and haven’t gone on your own workcation yet, then you’re missing out! Now’s a better time than ever to start planning your first workcation at Hilton Head Island. Read on to see what your Hilton Head Island workcation could look like. 

Wake Up Refreshed In Your Beautiful Hilton Head Vacation Home 

For us, one of the best parts of visiting a new place on a workcation or vacation is that feeling of hopping out of bed in the morning in a new place. And trust us when we say that mornings, especially sunrises, at the east coast paradise of Hilton Head make for some spectacular starts to the day. 

Although any one of our Island Getaway vacation rentals captures that magical Hilton-Head-morning feel, the best of the best mornings for your workcation will be at our ocean view rentals

Settle In For Some Morning Work Before Heading Out For A Seafood Lunch 

After taking the appropriate amount of time to absorb the majesty of the morning, it’s time to settle in for some work. With our properties’ fast internet access and comfortable interiors, work will fly by like a breeze. Once the first part of your shift is done, head out into town for a fresh seafood lunch break. 

Whether you’re visiting Hilton Head for your first or hundredth workcation, you have to head to The Crazy Crab for your seafood lunch break. For over 30 years The Crazy Crab has served up incredible fresh seafood dishes every day for hungry patrons from their two locations. The stars of the show are their award-winning crab legs which are a local’s favorite item. 

The only problem with taking workcation lunch breaks at The Crazy Crab is that you’ll know what you’re missing when you get back home. But don’t worry; we don’t have to talk about that right now. 

Work A Little Longer And Then Refresh With A Swim

After that hearty lunch at The Crazy Crab, head back to your vacation rental to get some more work done. Once you’ve put in a few more hours of work, take a breather to go for a quick swim at your communal or private pool. 

Several of the neighborhoods, like Sea Pines and Palmetto Dunes, have great communal pools that you can access during your stay. However, if you want to enjoy that more private refreshing escape, be sure to book your workcation in a Hilton Head rental with a private pool

Close Out the Workday with a Nice Meal and Walk on the Beach 

That last stretch of work for the day always brings a little challenge no matter where you stay, but the end-of-day rewards will be so sweet at Hilton Head. Once you clock out, close down your laptop, stretch out for a moment and then get ready to hit the town again for a fabulous dinner. 

Although we insist on The Crazy Crab for lunch, we don’t have any particular recommendation for where to spend your post-work dinner. There are many exceptional Hilton Head dining options for any taste and budget. Discover South Carolina has an excellent list of must-visit restaurants to check out for dinner, or you can peruse more options on our dining page

After dinner and maybe a little dessert, the best way to close out the day is by taking a cool walk down one of the many Hilton Head Island beaches. The gentle ebb and flow of the ocean water provides a perfect wind down for your day of remote work. Finally, head back to your vacation home to ready yourself for bed and start again bright and early the following morning. 


That’s what your Hilton Head workcation could look like if you book your stay with Island Getaways. A perfect workspace, fantastic refreshing views, great food, and plenty to see and do after you get off the clock. 

To get started planning your workcation, browse our available Hilton Head vacation rentals