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About Us

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Meet the Team

Drew

Drew is a seasoned vacation rental manager with a decade of experience in the industry. As the founder and owner of South End Hospitality, Drew has established expertise in optimizing operations and delivering exceptional guest experiences. Prior to venturing into property management, Drew managed restaurants, honing valuable skills in guest service and team leadership. With a solid background in both hospitality and property management, Drew possesses a unique perspective and a knack for seamlessly merging the two industries. With a passion for creating memorable stays, Drew is dedicated to ensuring guests have unforgettable vacation experiences. Drew lives in Jamaica Plain with his two cats Olive & Saffron.

Nicole

Nicole, a 30+ year property management pro, sold her 3000-door long term property company in 2018 to enter the vacation rental industry. Her diverse experience spans long-term rentals, commercial spaces, student housing, and short-term accommodations, and she excels at operations management, budgeting, financial analysis, process improvement, and team leadership. Nicole leverages her expertise to maximize property efficiency and profitability. She’s also an animal lover with two cats and a lively puppy/team mascot, Ringo.

Tyler

Tyler is a highly experienced property management professional with over 5 years of expertise in the vacation rental industry. Drawing from his background as a skilled cyclist and mechanic, his attention to detail and hands-on approach make him an invaluable asset in ensuring the smooth operation of properties. By combining his technical expertise with a passion for guest satisfaction, Tyler excels at providing exceptional experiences for visitors. Residing on beautiful Cape Cod, he is well-acquainted with the local attractions and can offer valuable insights to enhance guests’ stays. With a commitment to ensuring memorable getaways, Tyler goes above and beyond to deliver outstanding service in the vacation rental space.

Our team is the foundation of our success, and we are grateful for each member’s contribution. You’ll have the opportunity to connect with Pia, Angel-Nicole, Karen, Hazel, Ivy, Dee, Catherine, Bea, Nicole, and Rovern, all of whom are eagerly awaiting your arrival. We are excited to offer you a warm welcome and make sure your stay is unforgettable.

History of South End Hospitality

We started Home Shar​ing on Airbnb by using a spare bedroom in one of our own South End apartments, to make some extra cash. We welcomed guests from the US and all over world, including France, Australia, and India. Sometimes we bring our guests with us to parties or share a bottle of wine with them after work. Listening to our guests’ stories, sharing our backgrounds, and helping them learn about the great city of Boston really makes the Airbnb experience special and unique.

We turned this passion for hospitality into a full service Airbnb management company, launching South End Hospitality in September of 2015.Our first contract was for complete management services for a small studio apartment in South Boston. Our business is growing, as we have added multiple listings in Boston and Cambridge, all using our signature Hand Us The Keys Service.

Whether you’re looking for complete Airbnb management services or just help with your Airbnb reservations, South End Hospitality wants to be your trusted partner. With over ten years of experience in the hospitality industry, you can count on us to maximize your profits and take good care of your guests.
Whether you’re looking for complete Airbnb management services or just help with your Airbnb reservations, South End Hospitality wants to be your trusted partner. With over ten years of experience in the hospitality industry, you can count on us to maximize your profits and take good care of your guests.

Recent Guest Reviews

The location was perfect and Charlesgate Suites were very quick

March 2024
5star rating
The location was perfect and Charlesgate Suites were very quick to respond to my messages. Overall the property was clean and the management was very accommodating. I would recommend to anyone looking for a stay in Boston!

Great location for Boston Uni, Fenway and shopping – beautiful

January 2025
5star rating
Great location for Boston Uni, Fenway and shopping – beautiful studio apartment – and a supportive host !

My large family came up for the weekend and we

May 2019
5star rating
My large family came up for the weekend and we got to stay in Drew’s brownstone. Plenty of space for all of us to spread out, very homey with all the kitchen items you could need, and very clean. The spots outback were the best amenity and added t…

We had a great long weekend at Lucas’ house with

April 2026
5star rating
We had a great long weekend at Lucas’ house with our two kids (3 & 6). The walkability to town and proximity to cafes and restaurants was perfect and the house had everything our family needed to be comfortable. There were only four of us but the …

We loved staying here! Perfect location, perfect house with everything

April 2026
5star rating
We loved staying here! Perfect location, perfect house with everything you could need! Easy to check in and get in touch with the host. Thank you!!!

Comfort and convenience in Boston’s South End

November 2024
5star rating
Walkability within the neighbourhood and district :several restaurants, also the wine emporium, Flour. Within walking distance of MFA, Boston Public Library. Google maps street view helpful for planning. The 202 unit is set up for success t…

We had an amazing “Stay-Cation” at this property and will

February 2019
5star rating
We had an amazing “Stay-Cation” at this property and will certainly rent it again soon!

Amazing location!

September 2025
5star rating
Amazing location!

We enjoyed our stay here for a girls’ weekend getaway.

December 2025
5star rating
We enjoyed our stay here for a girls’ weekend getaway. The home had everything that we needed and was just as it was described. The weather was really cold, but the home was well heated and cozy for our stay. Lucas responded to our questions quick…

Drew’s place was really charming. The garden in back is

October 2024
5star rating
Drew’s place was really charming. The garden in back is especially sweet. We were able to walk to some great restaurants. Had a great weekend!