Vacationing for months at a time was once reserved for the retired, elite, or lucky few with financial means. However, today’s travel landscape is all about a remote workforce filled with wanderlust taking their laptops on the road.

Work and Travel: Best Destinations for Monthly Vacations or Multi-Month Stays

Vacationing for months at a time was once reserved for the retired, elite, or lucky few with financial means. However, today’s travel landscape is all about a remote workforce filled with wanderlust taking their laptops on the road.

You may still have deadlines and phone calls to tend to during the day, but weekends, off days, and evenings are free to explore from the comfort of a monthly vacation rental. Here are some of the best places to work while traveling.


White, sandy beaches and warm waters await in Gulf Shores, Alabama. Although kid-free travelers will find plenty to see and do around the area, Gulf Shores earned a reputation for being family-friendly with attractions like The Track filled with bumper boats and other fun. 

Spend your day playing along Gulf State Park beaches, golfing, or zip-lining over the dunes or go wildlife watching along the Bon Secour National Wildlife Refuge. Then work through the afternoon heat or evening hours before joining your new neighbors for a cold beer around the fire pit.


Escape the cold weather to the deserts of Arizona for a temperate winter full of potential. After working remotely from your monthly vacation rental, favorite new coffee shop, or co-working space like WeWork or Serendipity Labs, head out and start exploring.

Choose a monthly vacation rental in Sedona for quick proximity to red-rock buttes, canyon hikes, tranquil spas, and unique art galleries. Known for its energy vortexes and mystical vibe, Sedona is ideal for anyone looking to unplug from the rat race and find a more relaxing way to work. 

If city life is your preference, Arizona is also home to Tucson with a wealth of museums and hiking, including the trails of Saguaro National Park and the Tucson Botanical Gardens. Over in the capital of Arizona, Phoenix welcomes urban travelers looking for outdoor fun, award-winning dining, and vibrant nightlife in the Valley of the Sun.


Head west and settle in for a multi-month work-life vacation along California’s coastline

Whether you want to stay in wine country or enjoy the ocean breezes, you can find something for everyone in California. 

The tricky part is picking where to go first. Depending on your recreation of choice, try San Diego for culture and dining with proximity to the beach or Santa Monica for leisure at the beach. Havasu Lake, Shell Beach, Pismo Beach, and Palm Desert are all popular options. Choose an option central to your favorite pastimes and enjoy getting to know your new home away from home state.

The Caribbean

The hardest part about working in the Caribbean is tearing yourself away from the beaches, waterfalls, and town squares to get some work done. Just make sure to book a monthly vacation rental in a villa or reasonably upscale accommodations as WiFi can get spotty while working in paradise. 

You can also loosely consider Costa Rica as part of the Caribbean for this round-up and enjoy the rugged, rainforested coastline and wildlife watching in spots like Parque Nacional Manuel Antonio or Monteverde Cloud Forest Reserve. Costa Rica is also home to active volcanoes with hiking and hot springs for phenomenal outdoor recreation for an "only in Costa Rica" experience.


The Sunshine State is always a smart bet for multi-month stays. Take your pick of Florida vacation rentals whether you’re looking for something near the Emerald Coast, boat friendly, adjacent to amusement parks, or tucked away along the Florida Keys. If you’re not sure where to start, the 30A route is full of laid-back beach towns with a friendly vibe. 

During off-season months like fall and early winter, monthly vacation rental rates in Florida are typically lower than the height of winter, spring, and summer. You also get the added benefit of fewer crowds and other snowbirds and work-life balance seekers taking their careers on the road.


Work and play in the Aloha State, where year-round sunshine and tropical landscapes greet visitors. Hawaii may be small in comparison to its mainland neighbors but is diverse with jungles, beaches, cities, volcanoes, and even quaint pineapple farms. 

Consider a spot like Maui or Honalulu as your next monthly vacation rental destination and enjoy some of the planet's best beaches. Go snorkeling by day, fine dining by night, and squeeze in some work on island time. Hawaii also offers diverse monthly vacation rentals like high-rise condos packed with amenities, including pools and fitness centers in Honolulu, or a quaint cottage getaway in Kapolei.


Louisiana is widely known for its jazz, nightlife, and cajun flavor spilling out of New Orleans. You can have your fun at year-round festivals or escape to tranquility to the barrier island of Grand Isle nestled along the Gulf of Mexico. 

Take a hike along Grand Isle State Park, hit the beach, go fishing, and set-up camp on breaks from work. There's an abundant wealth of nature, including a Butterfly Dome and birding trails, but as Louisiana's only inhabited island, you'll have new friends and neighbors to share your catch with. Take your pick of Grand Isle accommodations with waterfront views and fishing piers. You can even snag a home fit for a fisherman with secluded boat access and fishing pier.


Mexico offers an affordable, warm, and relaxing way to spend a few months on the road. Although the country is vast with plenty of options nestled on the beach or mountain regions, an area like Playa del Carmen or Cancun offers tropical weather with proximity to dining, shopping, beaches, and "just in case" amenities including hospitals. 

Locals prove friendly and welcoming to foreigners, and Spanish isn’t usually necessary. Many popular coastal towns like Playa del Carmen also enjoy an influx of snowbirds and expats, making it easy to find new friends looking for adventure.


Try your luck in Biloxi, Mississippi for warm-weather fun and access to casinos, beaches, and history tours. The area is home to attractions like the Biloxi Lighthouse and Ship Island, drawing visitors to its laid-back beach life. Nightlife is plentiful in Biloxi, and visitors can pick from MGNM Park, casinos, and festivals to get to know their new neighbors.

Stay in a condo in Biloxi steps to the Gulf Coast with pools and outdoor recreation or across the water along Ocean Springs. Wherever you settle, ask about accommodations with waterfront views to watch the sunset after sending that last work email.


Stay in the Entertainment Capital of the World in Las Vegas, Nevada. The city is known for its world-class casinos like the Venetian or Mandalay Bay, but also features Broadway-caliber nightlife and around-the-clock entertainment. Beyond the nightlife, visitors and locals head out to Fremont Street for only in Vegas experiences like the Neon Museum or an outdoor shopping complex made entirely of shipping containers.

The city’s proximity to Sedona, the Grand Canyon, Hoover Dam, and Red Rock Canyon also makes Las Vegas an ideal location to escape the city. Condos are plentiful in Vegas for your work-life adventure, or if the bright lights are too distracting, stay just outside the bustle in areas like Summerlin along the TPC Golf Course. Opt for spacious rooms and pool access to escape the desert heat. 

New Mexico

Encompassing the Chihuahuan Desert and the Sangre de Cristo Mountains, New Mexico is home to art galleries, boutiques, Native American influences, and desert trails. Remote workers with a thirst for the outdoors head to Carlsbad Caverns National Park or the rare white gypsum sand dunes and trails at White Sands National Park. You can also brush up on your history with a visit to Chaco Culture National Historical Park for a look at an ancestral Pueblos.

Santa Fe is always a reliable option for remote workers who want urban amenities while exploring more of the southwest. Or stay in the tranquil Elephant Butte community for spacious accommodations in a Golf and lake community.

South Carolina

Business travelers may never venture past Charlotte to see the rest of what the Carolinas have to offer. However, take a month or two and explore South Carolina for a relaxed getaway filled with subtropical beaches, marshy sea islands, and historical coastal cities. A stop in Charleston is a must to stroll the cobblestone streets and take in the views of antebellum houses, boutiques, and pubs nestled along the French Quarter and Battery districts.

Take your pick of coastal destinations from Hilton Head to Myrtle Beach or Pawley's Island. All you need is your laptop and WiFi at South Carolina’s spacious homes, multi-room condos on the beach, and renovated beachfront houses. 


When winter travelers flock to Texas, locals greet them as “Winter Texans.” Join the warm-weather fun in St. Padre Island, Corpus Christi or Galveston, filled with historical attractions, walks on the beach, outdoor entertainment, and fine dining. 

Condos, homes, and cottages are common in Texas offering dog-friendly accommodations blocks from the beach and town. It's entirely possible to ditch your car altogether in favor of the free and easy lifestyle of being a Winter Texan.

Working on the road can also enhance your career with the ability to meet potential new clients, expand your horizons, and join networking groups. But the best part about monthly vacation is the ability to really settle in and unwind while exploring the area around you. It can also give you a new perspective on the idea that work will always be there, so why not take it on the road and make the most of your downtime from the beach?