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About Us

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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

Wonderful autumn getaway, convenient to town, fishing and bike path.…

October 2024
5star rating
Wonderful autumn getaway, convenient to town, fishing and bike path. The cottage is small but with spaces well thought out and meticulously furnished. Summertime renting might be more lively and congested in that area but off season it becomes a…

We stayed with another couple and our dog at Drew’s…

May 2023
5star rating
We stayed with another couple and our dog at Drew’s home for a long weekend mid-May. Each of us loved the home and all of the amenities it had to offer. The very quick and peaceful walk to the beach was ideal, and town with shops and restaurants w…

Amazing location!!! I’d suggest taking an early morning or evening…

June 2023
5star rating
Amazing location!!! I’d suggest taking an early morning or evening walk around the neighborhood. It’s a GORGEOUS area and the space it perfect. We traveled with 6 adults and 1 baby. It was very clean and had a lot of space for us. It’s very relaxi…

3 spacious bedrooms. Easy to use kitchen. Very clean bathrooms.…

August 2023
5star rating
3 spacious bedrooms. Easy to use kitchen. Very clean bathrooms. Easy parking. Most places on the Cape require you to bring towels and incidentals (toilet paper, soap, paper towels, kitchen oil, kitchen spices, etc..). Drew stocks all of these …

This was my second stay. Everything was spotless, bedding looked…

October 2024
5star rating
This was my second stay. Everything was spotless, bedding looked fresh. The temps were a little cooler so I loved snuggling under the down comforter. It was fun being so close to Kittansett and the water. Easy walk to the beach access or to the…

We truly enjoyed our stay! We were looking for a…

August 2023
5star rating
We truly enjoyed our stay! We were looking for a quiet getaway near the water and that is what we got. The house was well-kept, and well stocked, and we quickly felt at home. The beach was within walking distance – and the sunsets on the beach w…

This was the perfect location for our family of four.…

August 2024
5star rating
This was the perfect location for our family of four. Plenty of space for our young kids ans super close to the beach and rail trail. We were very happy with the responsiveness of Drew and would definitely stay here again.