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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

Great place to stay. Nice yard, nice views, nicely furnished,…

July 2025
5star rating
Great place to stay. Nice yard, nice views, nicely furnished, very clean, all the amenities we wanted in a central location that was a relatively easy drive to everywhere we wanted to go in Cape Cod. Would 100% stay there again.

Clean, bright and pretty.

September 2024
5star rating
Clean, bright and pretty.

Great place to stay and very nice! Great area so…

November 2024
5star rating
Great place to stay and very nice! Great area so close to everything! Clean, great bed, nice bathroom and room to relax vs some places in Boston. Clean and very quiet. We will def be back!

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!

Loved this place. AMAZING location Great base to explore Boston…

January 2023
5star rating
Loved this place. AMAZING location Great base to explore Boston on foot. One block to Boston Common, 10 mins to North End. Freedom Trail is right around the corner. Probably the biggest AirBnB we’ve stayed in with our family of 5. Plenty of room t…

We had a fantastic stay at Drew’s. Space was very…

August 2024
5star rating
We had a fantastic stay at Drew’s. Space was very clean and cozy. Great location. Mt friends and I come to Boston frequently and my friend said this has been her favorite place we’ve ever stayed

Expect a beautiful spacious home at a working farm with…

October 2021
5star rating
Expect a beautiful spacious home at a working farm with gorgeous views. A grand kitchen and dining room to cook and dine in and an in ground pool. Highly recommend.

Great place to stay for the weekend!

October 2025
5star rating
Great place to stay for the weekend!

Highly recommended! Everything about this apartment was great. The place…

July 2023
5star rating
Highly recommended! Everything about this apartment was great. The place feels new and as described. Very well kitted out kitchen and everything was immaculate in all rooms. Perfectly located near to beaches and only 2 miles from the local Glouces…