Holiday rentals with a pool in Anne Arundel County

Place was great and large enough to accommodate 2 families (9 total people). We were excited to have a place with a pool but didn’t end up using it because it was a little chilly. Neighborhood was quiet and early morning walks were pleasant. Beds were comfortable too.

This place is the best!! My daughter graduated from Howard University this past week so we needed a larger home for our stay. The greenery surrounding the property is beautiful. The home is large enough to host a large family but cozy enough to still feel close. Danielle keeps the pool and jacuzzi clean and functional for all guests. I could go on and on… you won’t regret staying here!!

10/10, 5-star experience. Christine and Will were wonderful hosts and their home was amazing. Don’t scroll past this listing!

Peggy’s house is beautiful! The inside and the outside are just wonderful! The pool, hot tub are just perfect! Wishing only that the house could sleep 6 adults plus a couple of kids. The location is just perfect!

Fantastic stay. Veronica was an excellent communicator from pre-booking to check-out. House was very nice, but the pool was exceptional. Home was as described. Thanks for a great weekend.

Olga was a very nice and responsive host. The townhome was very clean and everyone had their own room and bathroom which is hard to find on Airbnb. The townhouse was easy to find and access. Overall, we had a good experience at the townhome.

I stayed here the week of my wedding and it was absolutely perfect! From waking up each morning to have coffee on the dock with my pups and husband, to the beautiful views from each room in the house, we truly had a lovely time and chose the right Airbnb for such a special week in our lives.

5 Stars – A Wonderful Stay! I had such a great experience staying at Raquel’s place! From the moment I arrived, she made me feel right at home. The space was exactly as described—clean, cozy, and thoughtfully decorated with everything I needed for a comfortable stay. Raquel was incredibly responsive and helpful, offering great local recommendations and making sure I had everything I needed. Her attention to detail and warm hospitality truly made a difference. I would absolutely stay here again and highly recommend her place to anyone visiting the area!

What a beautiful setting! As the others have said, it's in the perfect location with a beautiful view of St. Mary's church and the Maryland statehouse dome. Freshly renovated, you'll find a fully-tiled shower in place of the usual tub/shower combo. This is a perfect place for someone who does not like stairs. Easy access in and about the condo complex. The kitchen is fully equipped for anything you'd like to do, if cooking in. There are no curtains in the windows of the living space. There is a shade in the bedroom. The bed is comfortable, as are the sofa and loveseat. My husband and I stayed here for 6 months while our house was being renovated, and we felt quite at home.

This was an awesome stay! If you have infants their place is a must as it is easily baby proofed and has so many accessible items!

We’ve stayed here for a few years now. His place is always clean and quiet. Beautiful location and very comfortable.

My wife and I had a fantastic stay at this charming studio in Annapolis. It was cozy, spotless, and had everything we needed for a relaxing weekend escape. The space is thoughtfully decorated with a modern touch and had plenty of natural light. The bed was super comfortable, and we appreciated the little extras like coffee, an air purifier, and fast Wi-Fi. The location couldn't have been better—walking distance to downtown, restaurants, and the waterfront, but tucked away enough to feel quiet and private. Parking was easy, and check-in was seamless thanks to clear communication from our host. We highly recommend this place to any couple looking for a romantic, convenient, and well-kept spot to explore Annapolis. We’d absolutely stay again!

We had a great stay - location and such were perfect for us.

Sean’s unit is an amazing option for those who love a great place to relax with an amazing view. Sean is a great host and very communicative.

We stayed a week in Annapolis in November 2021. We wanted to use this location as our base to explore the Annapolis area, the Eastern Shore and see our son in D.C. Location was excellent. Historical District, City Dock and Eastport restaurants all very walkable. Condo was on a marina and fine for our needs. Kitchen was well stocked with with pots, pans and utensils (we stayed in for dinner a couple of times). A suggestion would be to have some glassware that is not plastic and some sort of additional lighting for the dining area. Small suggestions to an otherwise very pleasant stay.

Great host, great location. Walkable to great restaurants as right over the bridge from Main Street Annapolis. The pool is literally right in front of the apartment overlooking the water and the boats going by. The place is not huge but location, location, location.