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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

I went away for a long weekend with my sisters,

October 2020
5star rating
I went away for a long weekend with my sisters, daughter, and dog and we could not have chosen a better house to stay in! The house itself was gorgeous. Plenty of room for everyone to have their own space but it also had a homey feel to it. It was…

Absolutely love Drew’s place! This is our second time staying,

August 2025
5star rating
Absolutely love Drew’s place! This is our second time staying, and we couldn’t have loved it more. Convenient location, squeaky clean, and absolutely beautiful. This Airbnb is also particularly special because it’s where we stayed when I decided t…

The house was excellently located and even better than the

August 2025
5star rating
The house was excellently located and even better than the pictures showed – clean, airy, bright, and spacious. We thoroughly enjoyed our stay and would come back in the future!

Great communication thank you

October 2025
5star rating
Great communication thank you

terrific spot. easy walk lots of places. No brainer for

September 2023
5star rating
terrific spot. easy walk lots of places. No brainer for out of towners going to Fenway. fwiw other reviews comment on the frontage. St Marys Ct is basically a glorified alley. the apartment does look over the back of storefronts and grocery does…

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

May 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…

Had an amazing stay here. House was in a great

June 2024
5star rating
Had an amazing stay here. House was in a great location. Small, private and quiet neighborhood close to everything (beach, restaurants, stores…). It was fully equipped with everything we could have possibly needed during our stay. Only thing I’d s…

Very responsive and friendly. The place was absolutely beautiful and

July 2024
5star rating
Very responsive and friendly. The place was absolutely beautiful and very very clean. It’s a little noisy outside since it’s in a vibrant neighborhood but other than that, everything was perfect and according to the description

Amazing communication great location enjoyed our safe

May 2026
5star rating
Amazing communication great location enjoyed our safe

Nice location and clean

July 2024
5star rating
Nice location and clean