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
4.91
463 reviews
“Terrific home in central Annapolis.”
Steve
Stayed in November 2026
“Such an easy location! Walk to all things DTA. Perfect sleeping us with all of the beds! Our mids could get back and forth quickly. It was clean, and the kitchen had all the things we needed to prep a meal. Heat/Air were great! Wonderful stay!! Book it!”
Dodie
Stayed in November 2026
“Beautiful home, in a fantastic location and extremely responsive and kind host!!!”
Molly
Stayed in November 2026
“Great place to stay while visiting Annapolis! The location was perfect, with all the attractions, shops, and restaurants within easy walking distance. Annapolis is a beautiful city with so much to see and do. We really enjoyed our stay and would definitely recommend this place to anyone visiting the area.”
Paul
Stayed in November 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