Dedicated to the Art of the Stay

We don’t just manage properties; we curate experiences.

Our Story

At Escape Vacation Rental Management, we believe a vacation is defined by the memories created within a home, not just the four walls themselves. We began with a simple mission: to bridge the gap between premium property ownership and the modern traveler’s desire for a seamless, high-touch experience.

Today, we are a local, dedicated partner for homeowners who want to build wealth without the stress, and a trusted guide for guests seeking a place to truly relax, recharge, and feel at home.

The Escape Standard

Local Heart, Global Vision
We combine deep-rooted North Shore expertise with cutting-edge management technology. We aren't a distant agency; we are on the ground, ensuring every property is cared for as if it were our own.

Commitment to Transparency
Trust is built through communication. Whether it’s clear performance reporting for our owners or 24/7 support for our guests, we operate with total honesty and a "no surprises" philosophy.

Personalized Excellence
Every property has a unique soul, and every guest has a unique need. We tailor our marketing, maintenance, and concierge services to match the individual strengths of every home in our portfolio.

Meet Our Short-Term Rental Experts

Jessie Holly

Jessie Holly is the Director of Operations and Guest Experience at Escape Vacation Rental Management, where she serves as the operational backbone of the company and a trusted partner to leadership. Jessie thrives in the details, expertly organizing moving pieces and ensuring everything runs smoothly behind the scenes.

Before joining Escape, Jessie built her career in K–5 education, where she evolved from classroom teaching into directing entire programs. That background shaped her strengths in leadership, communication, and systems management—skills she now leverages daily to oversee Escape’s operations and guest services at a high level.

At Escape, Jessie leads all operational functions while also directing the guest services team to ensure every stay meets the company’s five-star standards. She is the primary point of contact for owners, providing proactive communication and trusted support, and serves as Shayla’s right hand in executing the company’s vision. Jessie’s ability to anticipate needs, solve problems, and keep everything running smoothly makes her an invaluable part of the Escape team and the experience they deliver to both owners and guests.

Director of Operations & Guest Experience

Shayla Farmer

Shayla Farmer is a Partner and Managing Director of Escape Vacation Rental Management, where she leads the company’s vision, brand, and ongoing pursuit of delivering an exceptional guest experience. Deeply involved in every facet of the business, Shayla brings a hands-on leadership style that blends strategic direction with day-to-day execution, ensuring consistency, quality, and continued growth across the portfolio.

With over 15 years of experience in corporate accounting and 9 years as a licensed real estate professional, Shayla offers a unique combination of financial expertise and market insight. Her background allows her to thoughtfully balance performance for owners while elevating the guest experience—continually refining processes, strengthening the brand, and pushing Escape to operate at a higher standard.

Partner & Managing Director

Partner & Growth Officer

Garrett Farmer

Garrett Farmer is a Partner and Growth Officer at Escape Vacation Rental Management, where he leads strategic partnerships and new market expansion. He focuses on identifying opportunities that support the company’s growth while maintaining its boutique, high-quality approach.

Garrett brings over 25 years of experience as a commercial real estate broker, with more than $950 million in completed transactions across commercial and residential assets. His background spans acquisitions, dispositions, and development across industrial, office, retail, multi-family, and hospitality sectors.

With deep expertise in real estate strategy, Garrett specializes in helping clients maximize asset value through strategic planning and tax-advantaged exit solutions. His experience working with both public and private investment firms brings a sophisticated, results-driven perspective to Escape’s continued growth.

Why We Do What We Do

The short-term rental industry is evolving, and we are here to lead that change. By focusing on proactive property care and meaningful guest interactions, we protect the long-term value of our owners' investments while delivering a consistently high-quality stay for every traveler.

Whether you are looking for a well-equipped space to work remotely or the perfect setting for a family reunion, our ever-growing selection of properties is designed to help you escape the ordinary.