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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

Great venue

April 2019
5star rating
Great venue

Great spot ! Def coming back

June 2023
5star rating
Great spot ! Def coming back

We had a great stay! The place is comfortable, super

September 2024
5star rating
We had a great stay! The place is comfortable, super clean, and lovely. It felt so open with large windows, high ceiling and lots of light. The building, the entrance and the outside hallway are also very charming. The location was perfect for…

Was such a great stay, perfect location to walk to

November 2024
5star rating
Was such a great stay, perfect location to walk to the prudential center, Fenway or hop on the T. The apartment was spotless and has all the necessities!

Perfect location to walk to Fenway Park! Place was very

August 2023
5star rating
Perfect location to walk to Fenway Park! Place was very clean and new. Bed was super comfortable! Andrew was very helpful before and during our stay. Thank you!

Exceptional

September 2023
5star rating
There are no comments available for this review

The Chester is truly a step back into an amazing

February 2026
5star rating
The Chester is truly a step back into an amazing 1920’s brownstone. Aside from the building itself, the room had wonderful amenities and it felt like home. Drew was extremely responsive and accommodating. The location was prime – so many things to…

Cannot beat the location! Convenient to everything via foot or

July 2018
5star rating
Cannot beat the location! Convenient to everything via foot or T. Hosts responsive and helpful! Perfect for two families. The bottom front bedroom w the two doubles would not be a good spot for light sleepers due to the food trucks making very ear…

The place was super clean and charming, a perfect space

September 2024
5star rating
The place was super clean and charming, a perfect space for me to unwind after busy days.

Easy check in. Clean space. Cute decor and comfortable. Husband

September 2025
5star rating
Easy check in. Clean space. Cute decor and comfortable. Husband and I enjoyed the location.