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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

This place was great! It was a bit hard to

June 2024
5star rating
This place was great! It was a bit hard to find at first because the gps was saying the address was under a bridge? 🤣 but we figured it out. it’s very central to a lot of things in boston. Had a small issue with the parking because they gave us a…

True Boston experience! Comfortable and so quaint! Great location-

October 2024
5star rating
True Boston experience! Comfortable and so quaint! Great location-

Drew’s place was just as described, safe, and easily walkable

October 2025
5star rating
Drew’s place was just as described, safe, and easily walkable to the other parts of the city. We had our kids with us and we still walked everywhere. No rental car needed. Buses, subway and easy walking areas made it easy to explore Boston! The r…

My large family came up for the weekend and we

May 2019
5star rating
My large family came up for the weekend and we got to stay in Drew’s brownstone. Plenty of space for all of us to spread out, very homey with all the kitchen items you could need, and very clean. The spots outback were the best amenity and added t…

We had a fantastic stay at this gorgeous townhome in

June 2026
5star rating
We had a fantastic stay at this gorgeous townhome in Back Bay! The location of this house could not be better. It’s on a quiet street, but just a couple of blocks away on Newbury street, there are endless wonderful options for food, shopping, etc….

The Chester is now my favorite place to stay in

November 2024
5star rating
The Chester is now my favorite place to stay in Boston! The location is fantastic: close to mass transit, shops, restaurants, NEC, Northeastern, the Pru, Newberry, Fenway. The unit is absolutely gorgeous (looks just like the photos)…we appreciated…

Wonderful

May 2024
5star rating

Peaceful location in Harwich Port

September 2022
5star rating
We had a wonderful time renting this cottage. It is surrounded by beautiful woods and landscaping so it is very private, but it’s also very close to the beach and other activities so it is convenient as well. The best of both worlds! Inside it was…
August 2025
5star rating

Very responsive; great location if you’re ok with hearing some

November 2024
5star rating
Very responsive; great location if you’re ok with hearing some traffic. Easy walk to kenmore square train and onto Charles river walking path. Easy check in process.