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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

No complaints, very convenient and clean, perfect for a girls

March 2025
5star rating
No complaints, very convenient and clean, perfect for a girls weekend! Loved how close it was to downtown.

Drew was a responsive host and his property is amazing.

August 2025
5star rating
Drew was a responsive host and his property is amazing. We had a wonderful few days relaxing!

Exceptional

June 2024
5star rating
There are no comments available for this review

We had a great time at Drew’s place. It was

September 2024
5star rating
We had a great time at Drew’s place. It was big and private, loved the backyard and the outside porch area. Comfortable for several families.

Great place with quality furnishings. Some rental places are furnished

September 2024
5star rating
Great place with quality furnishings. Some rental places are furnished with cheap stuff. This was not the case. Everything was high quality. It was clean and comfortable. The shower was one of the best I ever had. The laundry is free but…

If I could give this place more stars, I would!

March 2020
5star rating
If I could give this place more stars, I would! The home is so spacious and airy and gets amazing light all day long. The decor is stylish and modern with extremely comfortable memory foam mattress and a large leather couch that fit our entire gro…

We had a wonderful stay. There are some really good

October 2024
5star rating
We had a wonderful stay. There are some really good restaurants near by and train/bus stops where a close enough of a walk so we can get around the city.

The house had a beautiful open feel, was impeccable and

March 2021
5star rating
The house had a beautiful open feel, was impeccable and the location was amazing. We had a great stay!
October 2025
5star rating

The location was perfect for dropping our daughter at BU

August 2024
5star rating
The location was perfect for dropping our daughter at BU and for exploring the many dining and shopping destinations in the area. We walked to most places but also took the T into the city center. The space was beautiful,clean, and had everything…