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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

נהננו מאד לשהות בדירה של דרו. הכל היה בדיוק כפי

June 2026
5star rating
נהננו מאד לשהות בדירה של דרו. הכל היה בדיוק כפי שהבטיח . לכל שאלה ובקשה נתן מענה מיידי. המטבח מאובזר היטב, הכל נקי. הגינה מאד יפה . אזור מצוין, רגוע, ביתי . ממליצה מאד על הדירה הזאת ובשמחה הייתי מבקרת בה שוב

We stayed at Lucas’s place weekend of Oct 25-27. From

October 2024
5star rating
We stayed at Lucas’s place weekend of Oct 25-27. From the time I chose to book the place until we left, communication was seamless. Lucas was very responsive. The place…i cannot stop to rave about it. Best airbnb we have stayed at. My adult kids l…

House was great! Spacious and exactly what we needed for

April 2019
5star rating
House was great! Spacious and exactly what we needed for a large group. Lucas and Drew were a great host. We had a small hiccup at check in and both Lucas and Drew were very responsive and fixed the issue in no time. The house was spotless and gre…

This is a really great space! The house is elegant

July 2024
5star rating
This is a really great space! The house is elegant and fun. The pool is large and the hot tub goes well with it all. There is lots of available bedding and common space to hang out. The host was responsive and communicative. We had no problems ar …

Drew’s place was very welcoming and felt homey for our

June 2026
5star rating
Drew’s place was very welcoming and felt homey for our staycation. Our dogs loved the backyard. The deck was a nice touch to have breakfast. Location was very quiet and peaceful, but also minutes to eateries and things to do. Just what we were lo…

Great location. Clean and very nice space. We had a

November 2024
5star rating
Great location. Clean and very nice space. We had a couple of issues—we couldn’t turn on the fireplace easily, and the battery of the front door lock went down and malfunctioned. But the representative was always there to answer and help us recove…

Un sitio muy agradable súper residencial , espléndido para conocer

September 2024
5star rating
Un sitio muy agradable súper residencial , espléndido para conocer la zona y muy del evento donde estábamos. Drew fue muy amable siempre nos respondió cuando teníamos alguna inquietud.

Beautiful place and a great location. Bikes are right down

June 2019
5star rating
Beautiful place and a great location. Bikes are right down the street and so is Fenway park, we loved this place. The steam room was priceless. I would definitely reccomend this house.

We enjoyed our stay at Drew’s place. The location is

December 2025
5star rating
We enjoyed our stay at Drew’s place. The location is fabulous! The apartment was just perfect for us. There’s a lovely back garden which we did not enjoy because the weather was so cold. I would love to return during warmer weather. Drew was very …

Beautifully appointed cottage with a very easy and SHORT walk

August 2025
5star rating
Beautifully appointed cottage with a very easy and SHORT walk to the beach for all ages. Ample room for 6 adults. Everything is there as if you were in your own home. Next to new Charbroil gas grill. Oceanview from deck and East facing bedroom. …