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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 had a wonderful stay. The house is spacious and…

April 2021
5star rating
We had a wonderful stay. The house is spacious and airy with great sunlight and a spectacular hilltop view of the town. We took long walks along Lake Mansfield, which is less than a half-mile from the house, and enjoyed going into town for coffe…

Would highly recommend this place its great for a large…

April 2021
5star rating
Would highly recommend this place its great for a large group. The location we walking distance to a grocery store, places to eat and the T stop which was very convenient. The apartment itself was larger than expected, very clean and well mainta…

Beautiful home close to Fenway and the restaurants in Brookline,…

September 2023
5star rating
Beautiful home close to Fenway and the restaurants in Brookline, and super close to the train to get around, and walkable to the river trail. The home had all of the amenities we needed, and the hosts were very good communicators. It was a perfect…

The apartment is clean and uncluttered and so beautiful!

May 2025
5star rating
The apartment is clean and uncluttered and so beautiful!

Lucas and Karen’s unit was the ideal place for our…

September 2022
5star rating
Lucas and Karen’s unit was the ideal place for our couples’ getaway. We all really needed a break and to relax and their unit was just what we needed. Spacious and comfortable, generally well outfitted, it was really easy for us to just unwind. We…

Awesome cabin in the Berkshires, centrally located to all the…

July 2022
5star rating
Awesome cabin in the Berkshires, centrally located to all the great towns!!! Thanks for a great stay!

Great stay for the weekend, great location in for goin…

November 2022
5star rating
Great stay for the weekend, great location in for goin to Boston and New England. House is beautiful in and out of it.

The house is amazing. Much larger than it seems. Very…

June 2023
5star rating
The house is amazing. Much larger than it seems. Very comfortable furniture and beds! Everything done so well throughout the entire place.