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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 a great stay, the location is very convenient

July 2025
5star rating
We had a great stay, the location is very convenient and the house is well furnished and appointed. Lucas was a very responsive host, too.

I appreciated how Drew reached out to me directly after

May 2026
5star rating
I appreciated how Drew reached out to me directly after booking to say hi and ask if we had any questions. The rooms were beautiful and the bed was especially comfortable with fresh linens and pillows. Thanks Drew! Karen

We love this house. We’ve had several stays over the

October 2024
5star rating
We love this house. We’ve had several stays over the years, and it never disappoints. The rooms are open and spacious while warm and cozy at the same time. The house is perched on a hill overlooking town against a backdrop of spectacular mountain …

Exceptional

August 2025
5star rating

Perfect location!

August 2024
5star rating
The location was perfect. Very close to downtown and in beautiful Back Bay. There is a lack of warm details. The decoration is very bland. Needs some warmth for a homier feeling.

Was such a great stay, perfect location to walk to

November 2024
5star rating
Was such a great stay, perfect location to walk to the prudential center, Fenway or hop on the T. The apartment was spotless and has all the necessities!

I stayed with my colleagues for work and the house

December 2017
5star rating
I stayed with my colleagues for work and the house was even nicer than we imagined! The location was very convenient, with a whole food supermarket right in front of the house. The host was kind and the communication was very smooth. We enjoyed ou…

We were very happy with our stay! Drew was accommodating

October 2024
5star rating
We were very happy with our stay! Drew was accommodating and responsive. We were in town for a soccer tournament and will absolutely rebook if we are back next year. We can with 4 adults and 4 children. The kids loved having a separate tv room and…

Very centrally located and easy to walk around. The place

September 2023
5star rating
Very centrally located and easy to walk around. The place was clean and very welcoming. The host was super responsive and available. So happy I booked this instead of a hotel.

We had a wonderful stay. The location was fantastic. We

September 2024
5star rating
We had a wonderful stay. The location was fantastic. We were able to walk to town for dinner, where there were so many options. Close to hiking. The place was spotless, had all the amenities in the kitchen, bedrooms and bathrooms. The proper…