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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

Drew was a very friendly and responsive host. The apartment

March 2026
5star rating
Drew was a very friendly and responsive host. The apartment was squeaky clean. A few issues with the breaker to the kitchen initially being flipped and lack of bedding for all the beds, but Drew responded promptly and issues were solved within a …

Beautiful and cozy apartment that’s in the heart of Boston,

December 2025
5star rating
Beautiful and cozy apartment that’s in the heart of Boston, you really couldn’t ask for more! Our host, Drew, was very responsive and helpful with any inquiries that we had. The apartment is also right next to a charming Italian restaurant named “…

Great stay. Very responsive. Warm and cozy.

November 2025
5star rating
Great stay. Very responsive. Warm and cozy.

Beautiful and convenient

August 2024
5star rating
Beautifully decorated, clean, and comfortable! Great location. We walked to Fenway Park and to various restaurants. It was a very easy Uber pickup location since there is a bus stop in front of the home. It was a short inexpensive Uber ride to a…

Very nice place to stay in Boston.5-10mins Uber to midtown.

September 2017
5star rating
Very nice place to stay in Boston. 5-10mins Uber to midtown. The house is very large and things are very convenient.

We had a fantastic experience staying at Lucas’ home. The

November 2017
5star rating
We had a fantastic experience staying at Lucas’ home. The location is great, the home itself is stunning, and our host was responsive to questions and communicated helpful tips about the neighborhood. 10/10 would return again.

This is now our second time staying here. We absolutely

May 2026
5star rating
This is now our second time staying here. We absolutely love the location, the unit was clean and comfortable for our family and we hope to go back again soon!

Beautiful , quiet setting and view; Good Harbor Beach is

September 2024
5star rating
Beautiful , quiet setting and view; Good Harbor Beach is just down the street and is one of the best beaches in Massachusetts IMHO. Felt cozy and was clean. Would stay again!

Stayed here while dropping our son off at college nearby.

August 2025
5star rating
Stayed here while dropping our son off at college nearby. Excellent location with about a 2 block walk to the Kenmore train and bus station. Walkable to Newbury St for great coffee and shopping. Super comfy bed and linens. We stayed in the cozy on…

From booking, communication to the stay was amazing. I cannot

November 2022
5star rating
From booking, communication to the stay was amazing. I cannot say enough good things about the location, comfort, responses in questions, and overall home away from home experience. It’s convenient to many local restaurants, the beach, stores and …