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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

We had a nice stay here with my family. Quiet…

August 2024
5star rating
We had a nice stay here with my family. Quiet location, and responsive host. Would stay again!

Beautiful home on a quiet street. Loved the care and…

July 2024
5star rating
Beautiful home on a quiet street. Loved the care and detail put into the upgrades and the pool was perfect!

I wish I was able to experience this place in…

October 2024
5star rating
I wish I was able to experience this place in the summer. It was exceptionally clean and beautifully decorated. My dogs had a yard to play in. I couldn’t have asked for more. I would stay here again in a heartbeat.

Strongly recommend this beautiful home. Spacious rooms and the location…

July 2021
5star rating
Strongly recommend this beautiful home. Spacious rooms and the location was perfect. Fishing, amazing restaurants, visiting several beaches were just minutes away. Chatham Center 10-15 minutes. We walked one day and drove other days. Lucas and Dre…

We had a wonderful time. Loved that you can walk…

July 2024
5star rating
We had a wonderful time. Loved that you can walk to the pond. We enjoyed watching the sunrise and sunset. Drew was very responsive with any question/inquiry. Little touches made the house cozy. We used the turntable a lot and enjoyed some music wh…

Tranquil view has a lovely large screened porch for morning…

October 2024
5star rating
Tranquil view has a lovely large screened porch for morning coffee and to enjoy the view. We had sunny fall days which were perfect to enjoy our trip. We walked to the beach a few times. I sat out there with a book a few afternoons. Golfed nearb…

Very clean, the house felt very cozy, loved the outdoor…

September 2024
5star rating
Very clean, the house felt very cozy, loved the outdoor Shower

The house was amazing, clean, and had everything we needed!

August 2024
5star rating
The house was amazing, clean, and had everything we needed!

A beautiful home in a nice quiet area

April 2021
5star rating
A beautiful home in a nice quiet area