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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 large group for a ski trip, and…

March 2023
5star rating
We had a large group for a ski trip, and this location was perfect! Very peaceful and close to a town where we could get gas and food. Lucas & Drew responded very quickly to my questions and checking in/out was super easy. Thank you for being such…

The home was beautiful and property peaceful.

August 2025
5star rating
The home was beautiful and property peaceful.

We truly enjoyed Thanksgiving week at the Farmhouse. The place…

December 2021
5star rating
We truly enjoyed Thanksgiving week at the Farmhouse. The place was large with plenty of comfortable rooms to relax in. It was clean and well stocked. Plenty of bedrooms for our large group too. Great location, very private

Great set up. Clean and well kept. Good location. Parking…

January 2022
5star rating
Great set up. Clean and well kept. Good location. Parking is an issue, but that’s Boston for you!! Lovely extra touches like coffee/filters for machine, washing powder and cooking stuff. Good communication throughout stay. Comfy beds and quilts.

Had a magical stay at this home — it was…

July 2023
5star rating
Had a magical stay at this home — it was very comfortable, spacious. Great access to the lake with kayaks & paddleboat. Or if you stay inside, there’s a fireplace and access to every streaming platform you can think of. Also, Lucas is super respon…

Great location that is close to everything! The knack behind…

August 2022
5star rating
Great location that is close to everything! The knack behind you is a great spot for quick bits. Our 2nd year back and would do it again

We used this as our home base for our daughters…

June 2023
5star rating
We used this as our home base for our daughters graduation from Berkshire school and it was absolutely perfect. Lucas and Drew made the whole process effortless for us. The house was so cozy and was not lacking in anything we needed. The settin…

We stayed at Andrew’s place for three nights after dropping…

August 2024
5star rating
We stayed at Andrew’s place for three nights after dropping our daughter off at college. It was in a great area of Jamaica Plain – an easy walk to Jamaica Pond, Centre Street, and the Stony Brook T station on the orange line. JP has great coffee s…

Amazing location, clean, modern and comfy. Great communication also. Had…

January 2022
5star rating
Amazing location, clean, modern and comfy. Great communication also. Had an amazing time.