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St Philip Square - The Distinctly Charleston Experience

The Distinctly
Charleston Experience

Inspired by personal experience, decades of travels, and a deep love for the Lowcountry, St. Philip Square is designed to exceed the expectations of today’s traveler with carefully curated and intentionally designed spaces.

Founded, owned and operated by Bill & Jacquelin Bennett, our local team seeks to provide stays that are as meaningful as they are memorable. 

The Grounds

The Grounds

Nested within the vibrant Cannonborough neighborhood, St. Philip Square is a collection of 6 restored historic homes with a spacious shared courtyard that span an entire city square block of downtown Charleston. 


Sitting neatly between Morris and Cannon Street, St. Philip Square is one short block from the hustle, bustle, wining and dining of Charleston’s famous King Street. Idyllically situated, we are less than half a mile to Calhoun Street and a stone’s throw from South of Broad. In short, location, location, location…


With our abodes originally dating back the early 1800s, St. Philip Square was carefully, intentionally and respectfully renovated by the end of 2020. Showing remarkable reverence for local history and devotion to the Lowcountry lifestyle, our accommodations have earned 5 coveted Carolopolis Awards from The Preservation Society and the esteemed Governor’s Award.


Acquired in the early 1990’s, St. Philip Square was grandfathered into offering permitted short-term vacation rentals by the City of Charleston. A rarity across downtown, this legacy allows our guests to experience the comfort of private luxury accommodations alongside the experience of true community immersion.  


With an unprecedented walk score of 96, most guests leave their cars in our spacious, protected parking area and easily stroll down to the restaurants, bars, boutiques, galleries and more mere steps away from their suite. 


Marrying new with nostalgia, ours is a uniquely Charleston experience. Explore our homes and suites or reserve your stay online today.     

St Philips Square - The Grounds

Meet The Bennetts

The Bennetts
St. Philip Square - Sign

First venturing to Charleston in 1960’s, Bill wound his way further south from UNC Chapel Hill to teach junior sailing at the local yacht club. A love story from the start, he met and fell fast for Lowcountry native, Ashley Hall teacher and Historic Charleston Foundation advocate, Jacquelin.


A force in the making, Bill secured his BS from UNC Chapel Hill and MBA from Emory University, while Jacquelin earned her AB from Sweet Briar College and MEd from The Citadel along with completing all her coursework and exams for a PhD in clinical psychology at Pacifica Graduate Institute. 


Over the years, this dynamic duo pursued many local business endeavors alongside raising their three children to include acquiring the St. Philip Square property in 1996. Among their numerous accomplishments and commitments to community enrichment, the pair pride themselves on earning 5 Carolopolis Awards from The Preservation Society and The Governor’s Award for the careful and intentional restoration of St. Philip Square.    


In 2001, the entire Bennett family crossed the Atlantic Ocean sailing from Wadmalaw island to London, England. Travelling far and wide across Europe, the Bennetts navigated their way from the Irish Sea to the Baltic Sea to the Mediterranean Sea, the Aegean, the Black Sea, the Levant Basin and North Africa before sailing their boat back to Charleston’s shores in the fall of 2017. 


For more than a decade, the party-of-five was its own captain, first mate, boat mechanic, navigator and cook. This incredible experience exposed the Bennetts to the wide-world of short term rentals as they selected local spots in the heart of wherever they visited from Paris, Istanbul, Avignon, Tunis, Rome, Procida, Venice, Corsica, Genoa, Stockholm, and beyond. 


On top of prime location, the Bennetts were attracted to accommodations with intriguing design displaying character and personality along with thoughtful touches and service that showed careful consideration of travelers. 


These shared experiences culminated into deep appreciation for the enlightenment and education that comes from travel along with a personal perspective for what travelers seek, need and value during their stays. All of which you will find intentionally invested back into every inch of Saint Philip Square.  


When Bill and Jacquelin take a break from designing and developing more of St. Philip Square, you may find them doting on their five grandchildren, playing freecell, reading astrological charts or nose-deep in a historic novel. 

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