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
Guest Reviews
What our guests say
4.9
410 reviews
“My family and I had a great time. The house was perfect to hang out and catch up. Close to great restaurants and sailing.”
Verified Guest
Stayed in September 2026
“great stay! so convenient and very livable”
Verified Guest
Stayed in September 2026
“Awesome stay in Annapolis. Responsive and welcoming host, perfect walkable location that’s still quiet at night, and very comfortable.”
Verified Guest
Stayed in September 2026
“Great house and very kind owners!”
Verified Guest
Stayed in September 2026
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.
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