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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

We stayed at this house for two nights with our

May 2025
5star rating
We stayed at this house for two nights with our young adult children and our dog. The space is generous. We especially enjoyed the open-concept living room, kitchen, and dining area, which made it easy to relax and spend time together. The entry r…

Beautiful space with lots of room for everyone. The location

May 2021
5star rating
Beautiful space with lots of room for everyone. The location in the middle of the city was just what we needed. The commercial location can be noisy but if you came to stay in the city that is expected. The proximity of the whole foods turned out …

This is one of the most beautiful appartments that I

February 2019
5star rating
This is one of the most beautiful appartments that I ever booked through AirBnB. Great location, wonderful spacious rooms, great kitchen area, perfect bathrooms; just gorgeous. And also excellent communication with the hosts. Highly recommended!

Loved every second of staying here! Drew was super informative

September 2025
5star rating
Loved every second of staying here! Drew was super informative prior to arriving, helpful with instructions on self check in. The place itself was spotless, made us feel right at home, it was exactly like the photos & the bed was so comfy (usually…

We really enjoyed our 7 nights stay, group of 11.

September 2022
5star rating
We really enjoyed our 7 nights stay, group of 11. Plenty of room to hang out. Well equiped kitchen. Walking distance to several amenities as advertised.

Had an awesome stay in Brookline. Lucas and Drew were

March 2026
5star rating
Had an awesome stay in Brookline. Lucas and Drew were super responsive and helpful. Would 100% recommend for anyone coming into town looking for a central place to stay!

Absolutely beautiful space!

October 2024
5star rating
Absolutely beautiful space!

Loved staying here! Amazing location, and the space is just

July 2025
5star rating
Loved staying here! Amazing location, and the space is just beautiful. Will be back again for sure!

This Brookline Airbnb is fantastic! Its beautiful and full of

December 2021
5star rating
This Brookline Airbnb is fantastic! Its beautiful and full of character. There is some noise from the trucks loading into the Whole Foods in front, but it didn’t disturb me and my coworker at all. The space is great for hosting and was super clean…

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.