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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

This was our second stay at this location and third

December 2025
5star rating
This was our second stay at this location and third at a location managed by Lucas for Christmas with our family. We are always happy with the cleanliness and description of the property. I would recommend this house and location to anyone looking…

Place was extremely clean and beautiful with modern furniture and

January 2024
5star rating
Place was extremely clean and beautiful with modern furniture and appliances. Hope to return some day soon!

This place is massive and a nice tucked away secret.

June 2019
5star rating
This place is massive and a nice tucked away secret. Super close to Fenway park makes this the ideal spot for a group of friends or couples to act as a staging ground for catching a ball game, or having a night on the town, quiet hours are taken v…

Wonderful stay! We celebrated a friend’s birthday as a group

December 2023
5star rating
Wonderful stay! We celebrated a friend’s birthday as a group of 7, with a toddler + a dog. Everything was exactly as depicted. The location was fantastic; easy walk to town. Space was perfect, plenty of room, very comfortable, and truly everything…

Exceptional

October 2024
5star rating

We absolutely fell in love with great Barrington, and the

July 2024
5star rating
We absolutely fell in love with great Barrington, and the house was such a great location! Very clean and perfect for kids. The yard was beautiful, as was the view. The town center is just a few minute walk away. We would love to stay again!

The place was great, so close to Fenway and walking

September 2025
5star rating
The place was great, so close to Fenway and walking distance to great restaurants and services. Highly recommend for a trip to Boston, especially for going to Fenway.

Old school cape house vibe with nice updated kitchen and

August 2025
5star rating
Old school cape house vibe with nice updated kitchen and decor. A great fenced in backyard for the dog. Walked to the beach and restaurants. Drew was very responsive. Short but sweet stay!

Restful place to recharge when taking in the sites of downtown Boston.

November 2025
5star rating
I liked the location, how central it was to the city. Also the hotel was very quiet and restful. It was a bit loud with the traffic but that’s not really something that can be controlled.

It was beautifully renovated and easily walkable to town. I

February 2023
5star rating
It was beautifully renovated and easily walkable to town. I have an electric car, so being able to walk to one was a game changer.