Family-friendly holiday rentals in Kent Island

Eric is an amazing host and person! Super friendly when it came to using the amenities and made us feel at home. Has great recommendations for food and local attractions. Beautiful property to walk around or just sit outside! Overall a 10/10 experience while staying at Eric’s home, couldn’t have asked for a better host for our weekend!

This was a very great find. Affordable for the part of the city we were in. Lots of energy and activity around the area, with plenty of places to eat/drink within a few block radius. Close to everything you need to be close to downtown. Easy check-in process. Beautiful, clean apartment. All in all, a wonderful spot to stay.

This house was absolutely central to all the activities we planned for our trip to Annapolis. Located in a wonderful neighborhood and a beautiful walk away from a tasty coffee shop!

Brooke's place was fantastic and it was easy to communicate with her. Everything was clear and as expected. Thanks Brooke!

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.

This home was the perfect place to celebrate my daughter’s graduation! We had family travel in from several states, and everyone felt comfortable and truly enjoyed the spacious layout. It was a bit too chilly to use the pool, but I’m already looking forward to booking this home again. I’ll definitely be a repeat renter!

Brandon's place was absolutely perfect! We couldn't have asked for a cleaner or more comfortable space. The location was great and Brandon is an amazing host. We would definitely stay here again!

Very nice place to stay near Gaylord convention center. Super clean condo. All the essentials are there. Lots to do at the resort as well as nearby walking distance. Having a baby in the group we did quite a bit of laundry. A laundry room was on our floor with two washers and four dryers and free of charge. We barely passed anyone on the seventh floor. We would def stay here again.

This 5th Wheel is like a water front Tiny Home. It is accurately described and pictured in the listing. It was clean and had everything needed for a short stay. It is in a working boat yard so it was cool seeing the owners working on and moving boats around. Also had some nice conversations with some of the people who dock their boats here. The marina itself seems very healthy. Clear water loaded with schools of bait fish so the blue heron, great egret and osprey were easy to spot. Unique and fun Airbnb. Highly recommend.

Perfect location if you’re in Annapolis for a game or just to visit the city. Christopher’s house was the perfect location and distance from everything in the city. Also, very spacious and nice house perfect for me and my 4 other friends.

Stayed here Memorial Day Weekend with my family of 4 and dog and had the most lovely time! The house is very clean and conveniently located to everything! Thomas was an excellent and communicative host. We will most certainly stay here again!

It was a very nice place. We had a great time.

Incredible place to stay! The hosts were flexible, responsive, and kind. Very accommodating regarding check in and check out. Would highly recommend!

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.

Stanley's place was a great for our two night stay. It is secluded and very private - the garden offers a private oasis and there's plenty of parking! We had four guests stay with tons of suitcases and space was not an issue. The house is older, but very clean. There are three bedrooms that can sleep 2 adults each. The bedroom off the living room is a little warmer than the rest of the house, just an fyi. The kitchen is well stocked with utensils, plates etc. Overall a great stay!

Exactly as pictured and described. Perfect stay and plenty of room. Beautiful back decks and yard. Great neighbors. Would stay again next time we are in the area.

Words can’t describe how incredible this home/property is! You have the option to just sit by the water or in the hammock watching the birds play and fish jump, or you can do one of the MANY activities Molly has provided for you. Kayaks, canoes, paddle boards, pickleball, yards games, pool activities, etc are all provided. The family room is all windows so it not only provides the most incredible breeze- it is great for enjoying all the sights even if you’re not outside in it. Inside there are tons of toys for kids- you do not have to bring a thing if you have kids. They have inside toys, outside toys, kids life jackets, goggles, water balloons, rafts, floaties, pack and play…. Molly and her family have thought of it ALL. We are already talking about coming back. Molly was the best host- responsive, helpful and inviting.

Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.

Calvin's place was exactly what we needed and much more. It was described accurately, yet exceeded expectations with tiny details. For example, there was not only coffee and tea available, but creamer in the fridge, too. We had a peaceful night sleep and a nice shower. I recommend this place to anyone needing a quiet space to work and stay in the area.

We found Paul’s home very comfortable and accommodating. Paul was accessible when we reached out to him and he communicated well with us. It was a very nice location with a fantastic view of the bay, as we hoped for.

David and Wendy’s home was the perfect place for our family participating in and supporting the Cambridge Ironman with an easy walk to the course and to the Main Street. They went above and beyond accommodating our requests, since we were traveling with a two month old and a two year old. We were very comfortable and loved our evenings in the screened in porch and pool. We would love to stay at David and Wendy’s again.

Nathan has a lovely home—it feels like stepping back in time into one of old Washington’s charming houses. Everything was spotless and well-maintained, and communication with Nathan was excellent. The location is convenient, about a 25-minute walk to Capitol Hill. While the surrounding area could be better—the streets were a bit dirty—it wasn’t a big deal and didn’t affect our overall experience. We had a wonderful time in Washington, and staying at this house was definitely part of it. Thank you, Nathan!

House is amazing!! Everything was perfect and well organized!! Will definitely be back at this property. Excellent communication.

The Woodland retreat is an amazing getaway! My sister and I were extremely happy to spend a weekend at the pool and can't wait to visit again soon!