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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

Had a wonderful stay at this property! The house looks…

July 2022
5star rating
Had a wonderful stay at this property! The house looks great in the photos and is even better in person. Enjoyed coffee on the dock every morning while looking out over the pond. Looking forward to to,returning again!

Lovely little apartment near plenty! Extremely walkable area of town.…

April 2024
5star rating
Lovely little apartment near plenty! Extremely walkable area of town. Very communicative and helpful! We had a great time

Drew’s home was perfect for our six family members attending…

September 2024
5star rating
Drew’s home was perfect for our six family members attending a local wedding. Having the two bathrooms was key! The super modern refrigerator was a nice surprise. The two indoor spaces to relax and watch TV we’re great and offered quiet in the fr…

We really enjoyed staying at Drew’s. The home was very…

October 2023
5star rating
We really enjoyed staying at Drew’s. The home was very clean, comfortable, and super well stocked with every item a short-term stay traveler might need. The location was private yet within an easy drive of shopping, restaurants, and so many thin…

Had a great stay at Drew’s! The gardens were lovely…

September 2025
5star rating
Had a great stay at Drew’s! The gardens were lovely and peaceful and the location was very walkable to whatever we needed. The home was cozy and comfortable.

EXCELLENT!!!!! Beautiful, comfortable home and gardens!

June 2025
5star rating
Positive: This house was extremely comfortable for us as a group and it was really nice to be able to cook and spend time together in a large open kitchen/dining space. The walk into town is easy, but the house and property feel like a private oa…

Lovely home! Really enjoyed that there were several separate spaces…

January 2023
5star rating
Lovely home! Really enjoyed that there were several separate spaces to relax, have a conversation, or be alone. The location is private but convenient to all the area has to offer. Hope to be back again!

We were very happy with our stay! Drew was accommodating…

October 2024
5star rating
We were very happy with our stay! Drew was accommodating and responsive. We were in town for a soccer tournament and will absolutely rebook if we are back next year. We can with 4 adults and 4 children. The kids loved having a separate tv room and…