Kid-friendly holiday rentals in Annapolis

Our Airbnb stay was absolutely fantastic! My family and I really loved all the amenities. The waterfront view was stunning, and we had a great time grilling and just hanging out together with friends and family. It was truly a memorable experience! I would definitely recommend this Airbnb for a family getaway and to have a peaceful time enjoying the water and the beach. I definitely will come back again!

We had a wonderful stay at this beautiful house. It was perfectly situated in quaint Annapolis, very close to the USNA, and as a family of Navy grads, we loved the convenience and nostalgic feel. The house was clean and very comfortable - beds, linens, and towels were clean and plentiful. The kitchen was a little sparse in terms of cookware and there was no drip coffee pot, but otherwise we made everything work. In hindsight, it was definitely on the expensive side of the spectrum for what it was, but we did have a wonderful time.

What a beautiful home and such wonderful hosts! Rob and Libby give more than just good customer service - the show true care for their guests. From the moment we booked, we knew that they would go above and beyond to make us feel at home. The check in instructions were easy to follow and there was a handwritten welcome letter waiting for us at the front door. The interior exceeded our expectations as everything was even more picturesque than the photos could capture. Lastly, when my husband and I locked our car keys inside, Rob responded to our phone call so quickly! He gave us clear instructions even stayed on the phone until we got our keys back. In the big ways and the small, we felt right at home. I would absolutely recommend staying here!

Our stay at Justin’s Hot Tub Haven in Annapolis, was exactly that…a haven with a much enjoyed hot tub! Justin was exceedingly responsive, proactive, and flexible. The home is very well appointed with all the necessities, plus all the thoughtful touches like umbrellas, a doggie waste station, and bath robes to name a few. Our children loved the downstairs space (and secretly the adults were thrilled they had it too), and it felt to them like they had their own little apartment. The backyard felt like a small resort. We loved the quick walk to shops and the our boys loved the nearby basketball courts and baseball fields. We highly recommend this home and will stay here again!

Had a wedding at the Chesapeake yacht club and its location worked great! Beat staying in a noisy hotel. Loved sitting on the dock. Very quiet place to relax. House looks small but that is deceiving. Place has room for everyone to Find their own quite relaxing space.

We loved staying right on Fleet Street right near all the action! Super fun and awesome area and great accommodations! Highly recommend

We had a fantastic experience. The home is full of charm and character. It was spotless upon arrival and had everything we needed for a relaxing stay. The location is unbeatable — just a short walk to the waterfront, and plenty of great restaurants and shops. We especially loved how quiet the neighborhood felt despite being so close to downtown. Communication with the host was seamless, check-in was easy, and every detail felt well thought-out. We would absolutely stay here again and highly recommend it to anyone visiting Annapolis.

Beautiful place, beautiful location. Joel thought of anything you could want.

I loved the area, calm neighborhood, the inside is big enough to host up to 9 people. She respond very quick, I have good time, I would recommend it to friends.

worth the price. situated a stone's throw from bwi.

This place was so peaceful. I really felt comfortable and relaxed. It’s a very beautiful area.

Absolutely amazing! The place had so much to do whether it was outside or in! Swimming in the pool, hot tub, kayaking and/or paddle boarding on the lake, giant yard games. Inside had a pool table, wide variety of board games, and many streaming services. Brenda was extremely friendly and helpful in many way. She had a binder full of local places for food and things to do! She truly showed us the best of Maryland.

We had a wonderful stay at Shawn's place. It is located in an absolutely beautiful area with a gorgeous view of the water. The place was beautifully decorated, and the bed was very comfortable. There were plenty of places to relax outside with a view of the water. We enjoyed taking the kayaks out and watching the sunset each night. Shawn was a lovely host and is a genuine person who wants you to have the best stay!

Great place to stay in Eastport. A couple doors down from Vin 909 Winecafe, which we highly recommend.

Joyce was the most welcoming host we have met in our many AirBnb stays. She wanted to learn about us and wanted to personally welcome us as soon as we reached her home. The basement apartment doesn’t feel like a basement. Extremely clean and well provisioned for us . The most powerful experience was how our interaction with Joyce and her family left us with a new FRIENDS in Annapolis, pleasantly way above our initial expectations! We highly recommend Joyce’s home for visits to the Annapolis area! We’ll be back at Joyce’s place!

Lynn's home was wonderful and quaint. The bed was comfortable, the kitchen and living area were perfect, and my stay was enjoyable. I'll stay again when I visit the Annapolis/DC area in the future! Thank you Lynn!

Ellen’s condo was absolutely perfect for Commissioning Week. The location couldn’t have been better—within walking distance to fantastic restaurants, the Naval Academy, and Graduation at the Navy-Marine Corps Memorial Stadium. The coffee shop downstairs was a delightful bonus, and the underground parking was a major perk. Ellen provided clear and detailed instructions about the condo and guest expectations, making everything easy to understand and stress-free. The condo itself is beautifully and tastefully furnished, with all the essentials thoughtfully provided. The in-unit washer and dryer were a huge convenience. The bathroom was spacious and well-appointed, complete with shampoo, conditioner, and body wash. What I appreciated most was how quiet and peaceful the condo was—it offered a true retreat. The private patio was perfect for enjoying a morning coffee or an afternoon cocktail. I would absolutely stay here again.

We can’t say enough good things about Megan’s place. Our favorite part was how well-appointed the kitchen is, but it’s all great. Very walkable/bikeable city, so you can leave your car behind.

Abaad was very nice, proactive, communicative. The Airbnb was nice, as pictured. Would stay again.

I was impressed by how clean and uncluttered Ricky’s place was. It was definitely a benefit that parking was included, though it was a little awkward loading and unloading and getting to and from the parking garage. Garage was a block away and secure with lots of cars nicer than mine haha.

Chris was a great host making check in and out so easy and flexible! The location of the place was perfect for walking to the market and to get coffee! The space was exactly like the pictures and perfect for a quick getaway with my fiance! Recommend this place!

Willie’s place is at a spectacular location with great access to buses/trains to both DC and the Pentagon area. Overall, a very safe neighborhood and the apartment is in great conditions. While you can hear upstairs people’s footsteps, it didn’t bother us much since the amenities and cookwares were very convenient and of great quality. Totally recommend for anyone looking to visit DC area :)

Ben’s place is exactly as described me and my family enjoyed our stay. I felt right at home, when I’m visiting my sister in the near future I will definitely stay again.

We absolutely loved our stay in this beautiful condo. Pristinely clean and spacious with everything we needed to be comfortable. We loved the modern decor and appreciated the extra thoughtful amenities. A wonderful place to return to after a long day of walking in DC. We would definitely stay here again and would highly recommend it to others.