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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

Nice and clean! Great place, Next to the long pond.

June 2022
5star rating
Nice and clean! Great place, Next to the long pond. My kids and dogs had great time there. Strongly recommended.

Easy and friendly experience!

July 2026
5star rating
Easy and friendly experience!

Good location, very nice house with good amenities as well!

February 2024
5star rating
Good location, very nice house with good amenities as well!

This house is amazing. Walkable to the beach, a short

July 2024
5star rating
This house is amazing. Walkable to the beach, a short drive to Main Street and plenty of room for the family. Couldn’t have asked for a better spot to spend our family vacation!

Perfect location to explore the South End. Walkable to everything.

July 2025
5star rating
Perfect location to explore the South End. Walkable to everything. I left a rather expensive suit behind hanging in the closet and Drew went out of his way to make arrangements for it to be returned. Would stay again!

Lots of room to spread out, walkable to T line,

May 2018
5star rating
Lots of room to spread out, walkable to T line, BU, Whole Foods, other universities, restaurants. Comfortable and accommodating, will be back!

Drew’s place in Harwich was wonderful and stocked with all

May 2022
5star rating
Drew’s place in Harwich was wonderful and stocked with all the essentials and more to make our stay comfortable. We also appreciate that it’s dog friendly. A nice surprise was that the house looked even better in person than in the pictures. The b…

Lucas and Drew’s place exceeded our expectations and lived up

December 2021
5star rating
Lucas and Drew’s place exceeded our expectations and lived up to the beauty of the pictures. The house is just a short walk to the shops and restaurants in downtown GB. Highly recommend a 4 wheel drive vehicle to get up the hill even in dry condit…

Perfect place for our perfect get away! Walkable to beaches,

July 2026
5star rating
Perfect place for our perfect get away! Walkable to beaches, restaurant. Even the neighbors very friendly. Our dog loved the fenced in yard, and the outdoor shower was clutch for after the beach! We can’t say enough about how happy we were to stay!

Had a fun time with family at Drew’s place. It

July 2023
5star rating
Had a fun time with family at Drew’s place. It was very warm so we appreciated the well working air conditioners in all the rooms. Being able to walk to nearby Long Pond that has a nice beach was great with small kids. And the game room was a big …