Your memorable Annapolis vacation starts here
Vacation rentals near the Chesapeake Bay, historic downtown, and Annapolis's best waterfront attractions. Book direct to save and unlock perks.
Available properties
Welcome to PMI Annapolis
Locally owned and independently operated, PMI Annapolis has served Annapolis since 2021. We manage premium vacation rental homes across 10 communities for guests who want an exceptional stay and property owners who want exceptional results.
Book with confidence
Why book direct with PMI Annapolis?
Best rate guarantee
Exclusive guest perks
Local support from day one
The PMI difference
Hospitality at heart
Every PMI Annapolis stay comes with our signature hospitality standards. From the moment you walk in, you will feel the difference.
Verified quality
Every home inspected and up to standard.
Spotless stays
Hotel-grade cleaning between every guest.
Local know-how
Insider tips from a team that lives here.
Guest Reviews
What our guests say
4.9
366 reviews
“Great house for a big group. Clean, walkable to a few restaurants, and host was always responsive. Highly recommend!!”
Verified Guest
Stayed in August 2026
“We had a wonderful stay! The house was spotless, with fresh, comfortable bedding and a cozy, well-equipped kitchen stocked with beautiful dishes. It was tastefully decorated with charming nautical touches that perfectly matched the Annapolis atmosphere. The location was perfect, and Danielle was an amazing host—she responded to every question within minutes. We would for sure stay here again!”
Verified Guest
Stayed in August 2026
“Fantastic location! Very responsive host. Can’t wait to return.”
Verified Guest
Stayed in August 2026
“Danielle and this location was incredible! It was absolutely perfect for my bachelorette trip! So proactive and accommodating for my girls and me! The property was amazing and the views were amazing”
Verified Guest
Stayed in August 2026
Vacation rental management
Property management built to win
From weekend getaways to monthly stays, we manage it all and maximize your returns.
Questions around your stay?
Our portfolio