Historic Key West Vacation Rentals

Life is a less complicated in Key West. Clear the mind. Restore the dreams. Get down to business in ways you can never do on the mainland. Our 7.4-square-mile island at the southernmost point of the United States is a perfect place to create a corporate retreat or simply bring your laptop and work from the beach or front porch with your morning coffee.

Historic Key West Vacation Rentals creates custom corporate environments for the most discerning guests. Our privately-owned homes include charming Key West writer’s cottages tucked away on secluded lanes and expansive, modern luxury town homes with the privacy and security needed by corporate and celebrity guests. Our fully furnished homes meet our high standards for luxury amenities, decor, location and customer service, as well as the stringent CHBO Complete guidelines.

Historic Key West Vacation Rentals is a locally-owned company located in the heart of Old Town Key West. Many of our homes are owned by long-time clients who trust us to maintain their homes and manage their guest rentals. We are Key West residents with deep and broad experience in vacation rentals, concierge services and the best that Key West offers in after-hours living.

Our homes are located within Key West’s legendary Old Town district and its quieter and equally beautiful Meadows district. Key West’s neighborhoods are part of the island’s distinct historic appeal and accessible modern conveniences. With corner bakeries, Cuban coffee shops, restaurants, neighborhood grocers, attractions, and art galleries but steps away, few of our guests need more than a bicycle or golf cart to get around.

Each home is minutes away from the best of Duval Street’s famous entertainment, dining and shopping and the spectacular sunset celebrations at Fort Zachary Taylor State Park and Mallory Square – yet each home is an island of privacy for quiet conversations, intimate entertaining and concentrated work time, if work you must.

Each of our fully-furnished homes includes Wi-Fi, cable, luxury linens and exceptionally well-equipped kitchens and baths. Most include private pools and outdoor gardens, as well as on-site washers and dryers.

Parking is at a premium in Key West. Although a select few of our homes include off-street parking, our guests find they rarely need a car while in Key West. If you do, you’ll find our public parking garages and lots efficient and safe.

Historic Key West Vacation Rentals offers monthly rentals or extended stay homes for those seeking a respite from daily corporate life, or for those who’d prefer working remotely in our island paradise.  Many of our homes can also be rented for shorter periods – some for just a few days – which gives you an opportunity to craft a corporate retreat for team building.

We can offer custom housekeeping and provisioning services should your needs be more demanding than our included services.

The diversity of our elegant homes ensures we will have one that matches your corporate or work-at-home needs. Our two-bedroom, two-bath homes are perfect for two couples or a visiting family for a weekend. Our larger homes with as many as five bedrooms, most with en-suite baths, beautifully appointed kitchens and indoor-outdoor living spaces work well for larger corporate groups.

Since its earliest days, Key West has been a working town, capturing the imagination of U.S. presidents, like Harry S. Truman and John F. Kenney, and the souls of writers like Ernest Hemmingway, Tennessee Williams, Judy Blume and Shel Silverstein. Key West drew each of them to its restorative lanes and byways, unfolding the creative power of its tropical island and surrounding aquamarine waters.

Tourism and small businesses are our major economic drivers and the U.S. military maintains extensive operations in Key West and at the Naval Air Station in Boca Chica, just a few miles up the Keys. About 25,000 residents live full time in Key West, and thousands more visit the island for major festivals throughout the year, such as Songwriters and Fantasy Fest, as well as dozens of literary and artistic events that draw internationally known performers, authors and artists.

And, our weather is perfect. Rarely do our days exceed 90 degrees in the middle of summer. Our winters are in the high 70s and 80s. The occasional rain shower passes quickly and brings out our vibrant greens and lush colors. Each day is an invitation to bring your best thinking to a work-day project, then spend a few idle moments basking in sunshine and tropical breezes.

We encourage you to consider doing what we locals do: Live. Work. Love. All in Key West. We promise, you’ll find your new island retreat to be a perfect place for working from home.

Learn more about by visiting CHBO or check out their website – Call 1-305-296-1010 to learn more.

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