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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

We had a great stay at Charlesgate Suite! The place

September 2025
5star rating
We had a great stay at Charlesgate Suite! The place is spacious, clean, and in a super convenient location for exploring the city. The hosts were really friendly and quick to respond. Would definitely stay again when we’re back in Boston!

Great pool

September 2020
5star rating
Great location

Super clean and quiet. Close to green line so easy

November 2025
5star rating
Super clean and quiet. Close to green line so easy to get anywhere Back Bay walkable

An absolutely beautiful apartment and next to some delicious restaurants.

October 2025
5star rating
An absolutely beautiful apartment and next to some delicious restaurants. If you have the chance to stay here do it!

Can’t really say enough. Lucas was responsive and all instructions

July 2023
5star rating
Can’t really say enough. Lucas was responsive and all instructions were clear. The home was exactly as pictured on the Airbnb website. The property was just beautiful. We felt at home from the minute we walked in. The location was perfect an…

Wedding

October 2023
5star rating
Wonderful great location

This place is beautiful. Lucas was super quick and responsive.

May 2023
5star rating
This place is beautiful. Lucas was super quick and responsive. Would stay here again anytime.

This is an awesome house. The size is much larger

July 2021
5star rating
This is an awesome house. The size is much larger than stated in the description. House easily accommodated our large group. The close proximity to beaches make for a fun trip and for great morning walks.

Nice Christmas Stay in Boston

December 2024
5star rating
Great location. 3-5 mins walk to Kenmore station (green line). Clean and spacious apartment with great amenities. The host is responsive. No grocery store nearby.

Exceptional

September 2024
5star rating