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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 an amazing stay in Great Barrington. The location

January 2025
5star rating
We had an amazing stay in Great Barrington. The location was perfect and the house was incredibly clean. The house was so comfortable and spacious. Thanks again!

Stayed here while dropping our son off at college nearby.

August 2025
5star rating
Stayed here while dropping our son off at college nearby. Excellent location with about a 2 block walk to the Kenmore train and bus station. Walkable to Newbury St for great coffee and shopping. Super comfy bed and linens. We stayed in the cozy on…

Fantastic home, away from it all but right next to

April 2021
5star rating
Fantastic home, away from it all but right next to it all! Stylish and great ambiance! Thank You.

Great house in a great location. Very clean and spacious

November 2025
5star rating
Great house in a great location. Very clean and spacious bedrooms. Beds are super comfortable. Living room has amazing views.

Perfect location near BU, Fenway and the Back Bay area.

November 2023
5star rating
Perfect location near BU, Fenway and the Back Bay area. Comfortable furnishings in a beautiful building made for a great weekend stay!

Great place to bring a group of people. Open and

June 2018
5star rating
Great place to bring a group of people. Open and more than enough space.

Beautiful room at a great location. We were able to

August 2024
5star rating
Beautiful room at a great location. We were able to walk to all the places we wanted to visit. The bed and sofa bed were both comfortable. Everything seemed recently renovated and decorated with style!

Very clean and amazing bathroom. Large space with good amenities.

September 2019
5star rating
Very clean and amazing bathroom. Large space with good amenities.

The house was adorable, well kept and clean. I would

August 2024
5star rating
The house was adorable, well kept and clean. I would highly recommend.

Great place for families

August 2019
5star rating
Great place for families