Our Story

Thoughtfully matching guests with exceptional homes while providing customized management solutions for homeowners.

At Simply Midcoast Vacation Rentals & Property Management, we believe exceptional vacations begin with exceptional hospitality. For nearly 20 years, we've been helping guests discover the beauty of Midcoast Maine while building trusted relationships with homeowners throughout the region. Our experience has taught us that every property has its own story, every homeowner has unique goals, and every guest deserves a stay that feels thoughtfully matched to their needs. Whether you're searching for a cozy waterfront cottage, a classic village home, or a private estate for gathering family and friends, we take pride in connecting people with places they'll love. We're intentionally boutique, focusing on quality over quantity, so every homeowner and every guest receives personalized attention from start to finish.

Our Philosophy

Our mission is simple: to provide thoughtful property management and memorable vacation experiences built on trust, local expertise, and genuine care. We believe successful vacation rentals are about far more than reservations, they're about creating lasting relationships. We partner with homeowners to protect and maximize the value of their property while delivering exceptional service to every guest who chooses Midcoast Maine for their getaway. Our goal is to make ownership easier, vacations more memorable, and every interaction personal, professional, and welcoming.

About Jen (The founder)

My connection to the coast began long before my career in vacation rentals. I was raised in Maine and, as the daughter of a U.S. Coast Guard family, was fortunate to call three lighthouses home during my childhood—two in Maine and one in Massachusetts. When my father was stationed at the Coast Guard base in Rockland, Midcoast Maine became home, and it's where my husband and I have proudly raised our family for the past 30 years. 

Nearly 20 years ago, I entered the vacation rental industry as a housekeeper, eventually working in the office. That experience taught me that exceptional hospitality begins with the smallest details. Gaining firsthand knowledge of every aspect of the business and learning that trust, communication, and genuine relationships are at the heart of caring for someone's investment and creating unforgettable vacations. 

Today, Simply Midcoast Vacation Rentals & Property Management reflects everything I've learned throughout my career. I believe every home deserves attentive, personalized care, and every guest deserves a welcoming experience that feels effortless from start to finish. The lasting friendships I've built with homeowners and returning guests are the greatest reward of my work, and I'm honored to continue serving the community I've been proud to call home for decades. 

I look forward to welcoming you to Midcoast Maine.

~Jennifer Maynard, Founder & Owner 

Simply Midcoast Vacation Rentals & Property Management

Tailored Services

  • For Homeowners~ No two homes or homeowners are alike. That's why we offer customized property management solutions designed around your goals. Whether you're looking for full-service vacation rental management for an investment or support with specific services for your generational home, we'll create a plan that fits your property, your schedule, and your vision. 

  • For Guests~ Finding the right vacation home should feel exciting, not overwhelming. We take the time to help match guests with the property that best fits their group size, travel style, budget, preferred location, and aesthetic. From charming coastal cottages to spacious waterfront estates, we'll help you find a place that feels like it was chosen just for you.

Why Guests & Homeowners Choose Simply Midcoast?

  • Nearly 20 years of local expertise in Midcoast Maine vacation rentals. 
  • Boutique by design, personalized service instead of one-size-fits-all management. 
  • Carefully curated homes, from cozy cottages to luxury waterfront estates. 
  • Customized management plans that fit each homeowner's unique needs. 
  • Local knowledge to help guests experience the very best of Midcoast Maine. 
  • Relationships first. We believe communication, honesty, and attention to detail make all the difference. 
  • Quality over quantity. We intentionally limit our portfolio so every property and every guest receives the attention they deserve.