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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 & family are great hosts my family enjoyed it…

September 2023
5star rating
Drew & family are great hosts my family enjoyed it as I was busy with the cape cod symposium for behavioral health care and I loved it as well Thank you Jay

Ideal New England charmer, and perfectly situated. As advertised, steps…

July 2024
5star rating
Ideal New England charmer, and perfectly situated. As advertised, steps to the beach, great walking neighborhoods abound, and an easy walk to town if you don’t want to drive. Quaint and comfortable house, and never did we need to ping owner Dre…

This is a the place to stay if you are…

July 2022
5star rating
This is a the place to stay if you are coming to Southie. It was a 2 min walk to a whole row of great restaurants, nightlife, live bands, and other action. The house comes with a parking spot which is huge as the parking can be tight. The house…

It is a really unique space with easy access to…

September 2024
5star rating
It is a really unique space with easy access to transit, walking distance to restaurants and Fenway. The kitchen is well stocked and the beds are really comfortable. We would definitely return.

This house was great for our family of 5. House…

February 2022
5star rating
This house was great for our family of 5. House was well stocked and clean and the hosts were very responsive. Excellent location close to town. Ice storm made for an icy driveway and the uphill road approach but 4WD made it work ok.

Spacious house in a good location central to many things…

September 2023
5star rating
Spacious house in a good location central to many things to do on the Cape. It worked well for our 2 families with 4 adults and 4 kids. The pool was a highlight and the beds were comfortable. We had a few small issues that the management group add…

Immaculate house in great location. Owners are super nice and…

January 2022
5star rating
Immaculate house in great location. Owners are super nice and super helpful. Would definitely stay here again

Wonderful location, central to everything. Easy access to restaurants, airport…

April 2022
5star rating
Wonderful location, central to everything. Easy access to restaurants, airport and transportation. Responsive hosts and the place was well equipped and very clean.

This was my 2nd time staying at this unit and…

November 2024
5star rating
This was my 2nd time staying at this unit and it was another wonderful experience. My family and I are already looking forward to our next stay. Elliot and Layla are fantastic hosts!