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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

Très joli appartement dans un quartier résidentiel très élégant bien

October 2024
5star rating
Très joli appartement dans un quartier résidentiel très élégant bien situé.

Nous avons passé un merveilleux séjour chez Drew ! La

September 2024
5star rating
Nous avons passé un merveilleux séjour chez Drew ! La maison est spacieuse avec de chouettes extérieurs… nous avons apprécié le petit-déjeuner sur la terrasse et les s’mores au coin du feu. Les enfants ont adoré la salle de jeu. Parfait petit havr…

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!

Drew’s place was in a great location for our time

March 2025
5star rating
Drew’s place was in a great location for our time in Boston. The neighborhood was very walkable, felt safe, and very convenient to restaurants, coffee shops, and the airport shuttle bus stop was within walking distance. I was so pleased with how …

Everything we needed to have a really great stay, décor,

March 2022
5star rating
Everything we needed to have a really great stay, décor, high quality linens, warm hospitality from Drew and his team, all around perfect. 5 Stars!

We stayed at Andrew’s place for three nights after dropping

August 2024
5star rating
We stayed at Andrew’s place for three nights after dropping our daughter off at college. It was in a great area of Jamaica Plain – an easy walk to Jamaica Pond, Centre Street, and the Stony Brook T station on the orange line. JP has great coffee s…

Great spot, and perfect for our needs. Really nice home-like

July 2023
5star rating
Great spot, and perfect for our needs. Really nice home-like space including some kids toys, legos, and dressers in all the bedrooms upstairs: easy to unpack and relax in. Great walkablity to the beach! Nice to have the view as well. There is an …

We very much enjoyed our week at this wonderful home

January 2025
5star rating
We very much enjoyed our week at this wonderful home in Great Barrington! The house was perfect. It was spacious, comfortable, well-located, quiet, peaceful, and extremely clean. Lucas was a very responsive host and immediately answered any quest…

I love Lucas’ place. It’s truly amazing. I hope we

March 2018
5star rating
I love Lucas’ place. It’s truly amazing. I hope we can stay there on our future trips to Boston.

Such a nice apartment in the best (in my opinion)

June 2025
5star rating
Such a nice apartment in the best (in my opinion) part of South End. The neighborhood is quiet and clean and so close to Back Bay, Copley Square and lots of great eateries. The backyard is like a secret garden in the middle of the city. Drew is ve…