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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 spot in a great location. Would recommend!

July 2025
5star rating
Great spot in a great location. Would recommend!

We stayed here with our adult children for a weekend

April 2026
5star rating
We stayed here with our adult children for a weekend together in Boston. This is a beautiful apartment with all the amenities needed to enjoy a relaxing weekend together, with a lovely walk-out garden/green space just outside the living space. Com…

What a beautiful home! We were only there for 1

October 2017
5star rating
What a beautiful home! We were only there for 1 night but the accommodations were fabulous. Thanks, Lucas

The high windows provide so much natural light, and the

December 2020
5star rating
The high windows provide so much natural light, and the place was incredibly clean.

This is one of my favorite Airbnbs I’ve ever stayed

September 2024
5star rating
This is one of my favorite Airbnbs I’ve ever stayed in. I want to live here. Amazing location, beautifully designed and decorated, super cozy bed, great products in the bathroom. No notes at all – would absolutely stay here again.

We will be back, thank you for a hidden gem in Boston.

April 2024
5star rating
The check in was flawless, all done by an electronic key pad. The entrance is beautiful, well lit, with the charm of old Boston with its hand painted wallpaper and winding staircase. Our suite on the second floor was easy to get to and had more th…

The house had many positives that you don’t usually find

September 2024
5star rating
The house had many positives that you don’t usually find in a beach rental. There were plenty of hooks to hang towels and bathing suits (something that is often lacking for some reason), plus the huge back deck was an option for hanging beach stuf…

We had a wonderful stay and easily walked to Newbury

April 2026
5star rating
We had a wonderful stay and easily walked to Newbury street and then to Fenway to catch a Red Sox game. We were a family of four so our boys were on the pullout in the living room. There were no printed instructions for the pull it out (which was …

Plenty of room

August 2024
5star rating
1 BR on first floor, 5 BR on second floor. Numerous tvs everywhere. Nice patio and yard. Kitchen well stocked. Short walk to beach which is Hen Cove. Fun for kids to catch minnows, hermit crabs, shrimp. Beach is shallow and not crowded. Sev…

Wonderful

December 2025
5star rating
The location was great for our needs and the property was very clean.