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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

Room 2F: overall, a great stay! The hosts were very

April 2026
5star rating
Room 2F: overall, a great stay! The hosts were very responsive via text, and a luggage-related accommodation was granted. In a pinch, you can grab Korean fried chicken a couple blocks away, near the Kenmore T, or walk ~15 minutes east to Trader J…

Beautiful, clean space! Lucas was quick to reply to any

November 2017
5star rating
Beautiful, clean space! Lucas was quick to reply to any questions. Would definitely recommend to others.

We stayed in Hyannis so we could have easy access

September 2024
5star rating
We stayed in Hyannis so we could have easy access to the ferry for our planned day trips to Nantucket and Martha’s Vineyard. Molly’s Folly was a great place to return for peaceful rest between trips! The cottage is well appointed, comfortable and …

Great location and beautiful house

July 2021
5star rating
Great location and beautiful house

Great location close to Fenway. Cool spot.

September 2022
5star rating
Great location close to Fenway. Cool spot.

This place was perfect for my family of 4. It

July 2024
5star rating
This place was perfect for my family of 4. It was clean and beautifully decorated. It was cozy and great to return to after a long day. The amenities provided were top-notch, ensuring that we had everything we needed. The communication with Charls…

Amazing place in an amazing location. The house was clean

October 2017
5star rating
Amazing place in an amazing location. The house was clean and there was plenty of room for us. Lucas was also incredibly easy to work with. Would definitely recommend. 10 out of 10.

We had a great stay! Beautiful house and a perfect

August 2025
5star rating
We had a great stay! Beautiful house and a perfect location close to Harwich center

Amazing location, great price, and great space!

December 2017
5star rating
Amazing location, great price, and great space!

Wonderful apartment.

February 2025
5star rating
This is a wonderful apartment. Great location. Quiet and close to interesting sites in Boston. Very well equipped.