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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

EXCELLENT!!!!! Beautiful, comfortable home and gardens!

June 2025
5star rating
This house was extremely comfortable for us as a group and it was really nice to be able to cook and spend time together in a large open kitchen/dining space. The walk into town is easy, but the house and property feel like a private oasis. The …

The place was as advertised, and good for our purpose

July 2024
5star rating
The place was as advertised, and good for our purpose (event at Fenway). The parking lot is a little sketchy but my car was safe and we had no incidents. The upstairs guests were terrible neighbors but certainly no fault of the host.

⭐️⭐️⭐️⭐️⭐️Wonderful stay! The house was spotless, cozy, and had everything

August 2025
5star rating
⭐️⭐️⭐️⭐️⭐️ Wonderful stay! The house was spotless, cozy, and had everything we needed. Great location and an excellent host—highly recommend!

Although situated at a busy intersection, the building and accommodations

August 2024
5star rating
Although situated at a busy intersection, the building and accommodations are fabulous, very comfortable, tasteful and well appointed, within walking distance to many restaurants and South End amenities. Like other guests, we found parking in the …

I love the place. Everything is clean. A lot of

December 2025
5star rating
I love the place. Everything is clean. A lot of nice restaurant near by. The host is very nice, and response to my question fast. Highly recommonded

Great location. Cozy location to be in for a snow

February 2022
5star rating
Great location. Cozy location to be in for a snow storm. We would definitely stay here again.

House is exceptionally clean. The bedrooms were large and the

January 2022
5star rating
House is exceptionally clean. The bedrooms were large and the beds were comfortable. The common spaces were also very nice but slightly on the smaller side from what I had hoped for. The drive up to the house is steep and would only use an all whe…

Great stay! Excellent location, helpful host, plenty of space. Wonderful

June 2025
5star rating
Great stay! Excellent location, helpful host, plenty of space. Wonderful place for our family vacation.

Great stay here! Spacious and beautiful cottage! Beach in walking

July 2024
5star rating
Great stay here! Spacious and beautiful cottage! Beach in walking distance feels like a private beach, would love to stay here again!

We love this house. We’ve had several stays over the

October 2024
5star rating
We love this house. We’ve had several stays over the years, and it never disappoints. The rooms are open and spacious while warm and cozy at the same time. The house is perched on a hill overlooking town against a backdrop of spectacular mountain …