Rooted in Elevated Hospitality,
Driven by Passion
About us
With over three decades of experience in the world of high-end hospitality and international luxury hotel chains, our team brings a deep understanding of service, excellence, and guest satisfaction.
Short Stay Management was born from a passion for creating exceptional short-term rental experiences—combining the personalized touch of a private villa with the standards of a five-star hotel.
We don’t just manage properties—we elevate them.
A Boutique-Style Service, not a Corporate Giant
Kenny is the Founder of Short Stay Management, with over 30 years of experience in luxury hospitality, marketing, and property management. He began his career at the Waldorf-Astoria in New York City, building a strong foundation in five-star service and leadership. With degrees from Penn State and Johns Hopkins University, Ken has led branding and operational strategies for boutique villas and major hotel brands, earning recognition in INC. and Lodging Magazine. His focus on guest experience and excellence in property care defines the high standards at the core of Short Stay Management.
Ken Conklin
General Manager
Sidnee brings over 30 years of experience in luxury hospitality, and client relations. She has successfully managed operations, vendor coordination, and upscale service delivery for high-end hotels and premier condo Boards. Her extensive background with luxury properties in Baltimore and South Florida highlights her expertise in property enhancement and board communications. Sidnee’s deep understanding of luxury standards ensures that every client and property receives personalized attention, seamless service, and exceptional care.
Sidnee Steigerwalt
Client Acquisition Director
Philippe brings over a decade of experience in luxury hospitality and property management to his role as Guest Experience Director at Short Stay Management. Originally from Paris, France, he began his U.S. career with Nordstrom, refining his skills in high-end customer service before managing top-tier luxury condo properties in Baltimore’s Inner Harbor, where he earned multiple service awards and drove over $14 million in sales. At Short Stay, Philippe leads the guest experience with a personalized, five-star approach—ensuring every stay is seamless, elevated, and unforgettable.
Philippe Lespagnol
Guest Manager
Riccardo brings over 20 years of experience in luxury branding, design, and hospitality marketing to his role at Short Stay Management. He has led creative initiatives for top-tier brands developing everything from digital platforms to uniforms for Nobu Hotels and Ava Resort. At Short Stay, Riccardo oversees brand strategy, marketing, and guest engagement, ensuring every detail reflects the elegance and excellence of the luxury travel experience.
Riccardo Sabioni
Creative Direction
Integrity, Transparency, Hospitality
Our mission
These are the core values that guide everything we do. We believe in building long-term relationships with property owners and guests alike, grounded in honesty, clear communication, and genuine care.
From seamless operations to warm, personalized service, we are committed to creating experiences that feel both professional and deeply human. With Short Stay Management, what you see is what you get—no surprises, just exceptional service.
Ready to maximize
your properties potential?
Partner with experts who know how to drive bookings, boost revenue, and take the stress out of vacation rental management.
Contact us today and let’s turn your property into a top performer!