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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

We had an amazing stay! Walk out the front door…

July 2022
5star rating
We had an amazing stay! Walk out the front door and your right in the middle of it all! Would definitely recommend and would definitely stay again

This central Massachusetts location was perfect. Well appointed and in…

March 2023
5star rating
This central Massachusetts location was perfect. Well appointed and in a beautiful location on a small lake. Everything was ready including a shoveled walkway from the snow they received a few days before we arrived. The communication was perfect…

This charming house is located on a quiet cul de…

August 2023
5star rating
This charming house is located on a quiet cul de sac and about one mile away to a quaint little town. The house was spotless, the kitchen had every utensil you could imagine including a kcup machine and coffeemaker. It was very comfortable, and t…

Beautiful and comfortable space for our whole family as we…

April 2024
5star rating
Beautiful and comfortable space for our whole family as we said farewell to a precious family member at the local hospital. Only hang up was having only one parking space as we had several cars. Lucas was super helpful with providing information a…

Drew’s place was in a perfect location for our stay.…

April 2023
5star rating
Drew’s place was in a perfect location for our stay. It is close to the airport and the convention center. The location makes it pretty easy getting around via rideshare. The house itself is very warm and welcoming with plenty of communal space. E…

It’s a great place Nice, clean and convenience

October 2022
5star rating
It’s a great place Nice, clean and convenience

Great location, clean place, beautiful view from living room! Just…

July 2023
5star rating
Great location, clean place, beautiful view from living room! Just wish if we could watch some golf on tv. Excellent overall!

Just as described

June 2025
5star rating
Just as described

Clean well equipped house in a fantastic location.

July 2023
5star rating
Clean well equipped house in a fantastic location.