Pmi Annapolis

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.

Welcome to PMI Annapolis

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

Verified quality

Every home inspected and up to standard.

Spotless stays

Spotless stays

Hotel-grade cleaning between every guest.

Local know-how

Local know-how

Insider tips from a team that lives here.

Guest Reviews

What our guests say

4.9

342 reviews

“The Crabby Patty was fantastic! Not only was the house adorable but the location was within walking distance of everything in downtown Annapolis. We booked it for my daughter‘s wedding and it could not have been more convenient to be a block away from the church. Danielle was incredibly responsive, even at all hours. We ended up booking this house after our first Airbnb house was canceled due to a pending sale. Danielle helped us find this house and even let us in to look at it a few months before to make sure it was perfect.”

Happy Guest

Stayed in July 2026

“Enjoyed my long weekend - house is just as described. Nice neighborhood for walking. I walked to downtown Annapolis a few times. A little bit of a longer walk- maybe 25 mins to get downtown. But so much easier than driving. Cute neighborhood- lots of dog walkers :) Traveled solo on this trip and felt safe in my surroundings. Would definitely stay here again on the next trip.”

Happy Guest

Stayed in July 2026

“Beautiful home with great water view. House is updated and very comfortable.”

Happy Guest

Stayed in July 2026

“I would absolutely stay here again. This property made me fall in love with Annapolis a bit. Danielle was immensely helpful, kind, flexible, and always responsive. I loved every bit of my stay!”

Happy Guest

Stayed in July 2026

Vacation rental management

Property management built to win

From weekend getaways to monthly stays, we manage it all and maximize your returns.

Revenue & marketing

Maximize bookings and earnings with data-driven pricing and best-in-class listing exposure.

Dynamic pricing optimization

Listing optimization & distribution

Multi-channel marketing

Revenue & occupancy reporting

Direct booking growth

Guest experience & operations

Deliver 5-star stays with seamless communication, spotless homes, and on-the-ground support.

Guest communication & check-in

Professional cleaning coordination

24/7 guest support

Maintenance & turnover management

Quality inspections between stays

Questions around your stay?

Our portfolio

See the properties we manage across Annapolis

Browse our properties