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Meet the Team

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.

Alicia

Alicia is a hospitality enthusiast who transitioned into the world of short-term vacation rentals back in 2017 and never looked back. With experience across various aspects of property management, she now focuses solely on owner acquisition and finds joy in engaging with new homeowners, illustrating the benefits of partnering with our team! When not in conversation with homeowners, Alicia can be found enjoying outdoor adventures with her family and their lively Chesapeake Bay Retriever, Shuba!

Andrew

Andrew is a seasoned vacation rental manager with a decade of experience in the industry. As the founder and owner of South End Hospitality, Andrew has established expertise in optimizing operations and delivering exceptional guest experiences. Prior to venturing into property management, Andrew managed restaurants, honing valuable skills in guest service and team leadership. With a solid background in both hospitality and property management, Andrew possesses a unique perspective and a knack for seamlessly merging the two industries. With a passion for creating memorable stays, Andrew is dedicated to ensuring guests have unforgettable vacation experiences. Andrew lives in Jamaica Plain with his two cats Olive & Saffron.

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.
Stay On The Cape is the newest office for South End Hospitality, a vacation rental management company located in Boston. Since 2015, South End Hospitality has been managing short-term vacation rentals and limited-service boutique hotels in Boston and throughout Massachusetts.

Currently, they have over 50 single-family vacation rentals, on the Cape, in the Berkshires, and in Boston and manage a portfolio of boutique limited-service hotels with around 150 doors and growing.

History of Stay On The Cape

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

Really enjoyed our stay at Drew’s place. Drew had quick…

June 2025
5star rating
Really enjoyed our stay at Drew’s place. Drew had quick and responsive communication, was super friendly. The house was amazing – family visited for a week while I was working in the area, so really my only regret is that I didn’t get to spend as…

We really enjoyed staying at Drew’s. The home was very…

October 2023
5star rating
We really enjoyed staying at Drew’s. The home was very clean, comfortable, and super well stocked with every item a short-term stay traveler might need. The location was private yet within an easy drive of shopping, restaurants, and so many things…

Hi Drew, Thanks for being our host. We enjoyed our…

August 2022
5star rating
Hi Drew, Thanks for being our host. We enjoyed our stay. You were attentive to all our needs. The pool was beautiful. The location is very good. Close to everything you would need.

Beautiful home close to downtown Chatham. We are a small…

July 2022
5star rating
Beautiful home close to downtown Chatham. We are a small family of 3 and only used the main level, house sleeps SO many more guests. We loved the baths & hot tub. Pool was easy to open and close. Favorite feature was the living room and staircase, t…

Drew is an excellent host we would def stay here…

July 2024
5star rating
Drew is an excellent host we would def stay here again

Drew’s home was exactly like the photos, clean, comfortable and easy access to many beaches and downtown

September 2025
5star rating
Drew’s home was exactly like the photos, clean, comfortable and easy access to many beaches and downtown. Drew was incredibly responsive and communicative leading up to and during our stay. 5 stars!

Great stay! Beautiful home!

August 2024
5star rating
Great stay! Beautiful home!

Excellent home and location

September 2025
5star rating
Excellent home and location! Drew was a great host and very attentive. Highly recommend.