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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

Lucas’ place was terrific. Clean and light and a great…

July 2022
5star rating
Lucas’ place was terrific. Clean and light and a great location. We loved it!

We had a wonderful stay at The Chester! The apartment…

May 2025
5star rating
We had a wonderful stay at The Chester! The apartment is on the first floor of a historic brownstone with stunning original architectural details. It’s beautifully decorated and equipped with everything we needed for our stay. Fantastic locatio…

Clean and convenient. Would stay there again.

October 2023
5star rating
Clean and convenient. Would stay there again.

Great place to stay in Boston, walk to everything.

September 2024
5star rating
Great place to stay in Boston, walk to everything.

We had a great stay in this house. We have…

June 2022
5star rating
We had a great stay in this house. We have rented a lot of houses on Cape Cod over the years, and we were very impressed with the house, the size of the rooms, the yard, and the cleanliness and condition of the entire house. We loved the locatio…

It’s hard to put into words how beautiful and charming…

June 2023
5star rating
It’s hard to put into words how beautiful and charming this place was to stay. The perfect cape cod house. Incredibly beautiful surroundings and details of the house and yard. Incredible hosting, spotlessly clean, fantastic area. It was a stressfu…

This was a wonderful place to stay. Very roomy, clean,…

March 2023
5star rating
This was a wonderful place to stay. Very roomy, clean, beautifully decorated.

Good!

July 2023
5star rating
Good!

Great stay! Super convenient to BU and sites downtown. Really…

June 2024
5star rating
Great stay! Super convenient to BU and sites downtown. Really quiet and clean, comfy bed, cold a/c, and helpful hosts who resolved a minor issue with electrical outlets within minutes. We will return!