5 Remote Working Breaks In Key West

key west's southernmost point

This is the life. Remote working from a luxury boutique cottage or Conch home with the Caribbean and historic Key West as a part of your office decor. Historic Key West Vacation Rentals has the perfect home away from home for you and your friends or family. We offer everything from one-bedroom historic cottages tucked away on quiet lanes, to magnificent four-bedroom mansions located on Duval Street. Whether you prefer the pool or ocean, you're bound to find the perfect rental to accommodate your stay in Key West. All of our vacation rentals offer personal concierge service, a 24-hour on-call manager, free cable TV, and free WiFi. Still, whether you're working on a solo project, leading discussions via Zoom calls, or downloading school projects, work is work. Sometimes, you just need to get up, get out, and take a break.  Key West has it all when it comes to the arts, recreation, history, and fun.  Here are five of our favorite ways to take a break from work or school and the stresses of life.

Take A Bike

From our famous Historic District to the picturesque waterfront, bike riding is our favorite way to experience Key West. Our southernmost paradise measures about four miles by two and it’s flat, so you’ll have an easy go of it. We’re happy to help you enjoy adventures on bikes from our neighboring rental companies. You’ll ride in comfort with wide, fat tires, comfortable seats, baskets, and night lights. Cars are few and speed limits are low, so set your pace to enjoy our natural paradise, its cool architecture, hip, and happy hangouts, and the local characters you’ll meet along the way.  

Where To Stay

 The Truman Suites offers five separate fully equipped suites just a few steps from famous Duval Street. The two-story complex offers 7 bedrooms, 5 bathrooms, and sleeps up to 18. The Truman Suites collection includes 1-2 bedroom suites — Harry, Margaret, Martha, Bess Suites, and John Truman's Hideaway. These suites can be booked individually as well as grouped.

 Paddle Up

 When you experience the waterways of Key West, you’ll enter into a lush marine world of mangrove islands and patch reefs, and sponge gardens. Kayak through our various ecosystems to meet a variety of tropical birds, rays, sport fish, and the likes. Paddle across the Gulf of Mexico or explore our creeks and shallow water.  

Where To Stay 

Maisons de Luxe is located on Duval Street in Key West's Gallery District. The stunning main house (Maisons de Luxe) consists of two smaller properties: Grand Maison and Petite Maison. The entire property can be booked as a whole, or smaller groups can book each separately. 

Mask Up 

Fort Zachary Taylor is perfect for snorkeling close to shore. It’s widely considered to be the best beach in Key West. It's located at the southernmost tip at the end of Southard Street on Truman Annex. The historic fort was built in 1866 and the snorkeling is just as amazing as the structure. 

Where To Stay

Fair Winds at the Foundry is a gorgeous coastal 3 story, 2 bedrooms, 2.5 baths immaculate light, and airy end unit townhouse in the Foundry section of the Truman Annex. Walking distance to ALL that Key West has to offer!

 Stay Above Board 

Stand up and take it all in with SUP rentals in Key West. Paddleboard or paddle yoga, daytime or night, you’ll enjoy the beauty and the wonder of blue-green seas and our mangrove ecosystem. You can launch from Smathers Beach, Higgs Beach, Fort Zachary Taylor, Simonton Street Beach, and Sugar Loaf Key. 

Where To Stay 

Inn Cogneato Cottage is just a one-minute bike ride to the Southernmost Point and a three-minute ride to Duval St. You’ll love how close this home is to everything, yet how tucked away you feel.  

All Aboard 

Take a train ride through our history with tales of settlement through the boom time of railroad days, the depression, and the patriotism of World War II. This adventure will introduce you to the characters and places that make up Key West’s allure. 

Where To Stay

Casablanca Grande is the perfect get-a-way vacation rental for those seeking a good time, but would like to stay a short distance from all the Duval Street craziness! In addition to the private pool, hot tub, and in-wall A/C, this property also has designated off-street parking for 2 cars (one per unit). With the two units, you can also be close to friends or family but still, have your own private space. Casablanca and Casablanca Too each sleeps 2 adults comfortably and they can be rented separately or together

These are just five of our favorite ways to take a break from the work at hand. Our nightly and weekly collections make it easy for your to fly in and get the work done.  If you've come to work and play and then decided to stay. our monthly rentals collections can accommodate your needs for up to six months.

Key West is definitely not an all-work kind of place.  You deserve a break. You'll find our best remote work and remote learn vacation spots right on our website. Our vacation planners know all the best ways to take the breaks you need and how to live like a local, too!