
Kid-friendly holiday rentals in Kent Island
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Top-rated family-friendly rentals in Kent Island
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Popular amenities for Kent Island family-friendly rentals
Kid-friendly house rentals

Spacious4BR home with waterviews
5 adults, 2 children under age 6 stayed at Courtney's home, which was just as described and pictured on the airbnb web page. Great location for our stay for wedding weekend; very comfortable furniture (sofas, chairs, beds; many amenities provided for guests; terrific well-stocked kitchen; very large screened-in porch w/ nice view of Chesapeake Bay and surroundings; spacious bedrooms; 4 full bathrooms; very clean when we arrived. I could go on .... Courtney is a very good communicator, and responded quickly to the few questions we really had. She is a great host and the house was terrific for our needs.

Ruby Of The Bay
Can’t say enough good things about our stay! Beautiful place with everything we could possibly need. The kitchen was well stocked and our host had thought of everything! Clear instructions, great recommendations for local spots etc. And the huge backyard and deck was perfect for us and our pups. Very comfortable beds and pillows too! Finally, host communicated so well and was incredibly accommodating.

Waterfront Farmhouse Meets Modern Luxury
The house is beautiful and worked well for our family. The host was very helpful and responded quickly to any questions we had. The grounds are lovely and very peaceful. Pictures don’t do this property justice.

Away at the Bay: New Home on the Chesapeake Bay!
Cannot put into words how wonderful our time was at Away at the Bay! Just left my soon-to-be SILs bachelorette trip and the entire weekend was nothing short of incredible. Thank you so much to Ryan and Eric for creating such a wonderful experience in a place that truly feels like home but BETTER! Memories we will cherish forever.

Chester Delight- Fireplace/Deck&Patio+fenced yard
Had a great stay here with a large group for a local wedding! Would absolutely recommend for anyone needing a comfy spot for multiple guests on the island.

Rare New Build Home w/Hot Tub, Fire pit, Game Room
The place was wonderful. It was wonderful timely responsive My Children enjoyed themselves. My wife didn’t complain and she loves to complain so she didn’t have one complaint which made everything absolutely perfect and I would definitely book there again in the next time I visit Maryland. It was wonderful experience.

Waterfront Chesapeake mansion - Panoramic Bay view
We stayed in this house for our son's Naval Academy graduation/commissioning. It was absolutely perfect for our group. The drive across the bay bridge took anywhere from 35-45 minutes depending on the traffic. At no time was the traffic as bad as we've experienced it on the DC side of Annapolis. We crossed the bridge 1-2 times a day during our 7 day stay. As soon as you get to the island and head south there is no traffic and it's a beautiful, peaceful drive. The house is perfect for entertaining with two large rooms inside on the main floor. There is a large island in the kitchen room which makes for a great serving area. It rained during about half of our visit so we made good use of the space indoors. Our children used the fishing poles, kayak, soccer nets, ping pong and fooseball table. Negin was very responsive in answering our questions and even worked it out so we could check in early. We would definitely stay there again if we had the chance.

Bayview Bungalow - Water view, EV charging station
There were many more amenities than what was listed. It was much better than most 5 star hotels! The area was really nice and peaceful, all the neighbors just wave hello to each other, large property with BBQ, hammock, shed, table and chairs to just relax outdoors, a tub for an intimate time with a narrow cross table to set down your champagne, etc etc. The kitchen / dining room / family room was a large open area with so many utensils and items of convenience. It is pet friendly and there were items for the pets as well, a first aid kit, etc. It is a beautiful house on one level, very comfortable, extremely quiet and peaceful. Vicky was in communication throughout and gave clear and concise instructions, which made things very easy for us. Upon checking in, there is a booklet with all the guidance and instructions, information on sites to see and things to do, local restaurants, etc. She has really though of many things to make one's stay as comfortable and as easy as possible
Family-friendly apartment rentals

Quiet Cozy 1 Bdr Apt at BWI Airport
worth the price. situated a stone's throw from bwi.

One bedroom apartment in Annapolis
Lisa’s place was amazing! My daughter and I had a great visit. The location is perfect for going into Annapolis. We will definitely be back. Thank you for a great few days!

Private cozy cottage - center of Chestertown .
Had an amazing stay here! Bob and Beth were extremely responsive hosts and provided a lot of clear instructions on how to find the carriage house. It was very clean and spacious and had a great coffee set up. The surrounding gardens are so lovely! Was quiet and walkable to the local downtown area

Butchershill-Private Clean Cozy Fireplace Parking.
We chose John's place because it was a block from our Son's house in Butcher's Hill. We would choose it again because it was a beautiful place with everything you could need thoughtfully supplied. John was super responsive to every question and communication, which is a big plus. We would not hesitate to stay there again in the future.

Celebrate Summer by Your Private Pool
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.

A unique place on sue creek
This place was so peaceful. I really felt comfortable and relaxed. It’s a very beautiful area.

Charming Studio in the heart of St. Michael's, MD.
Place was nice and in a good location. Host was responsive. Good news is that it’s in a good location, but it is by the main road and can get a little loud, probably mostly on weekend nights. But places close early, so noise doesn’t last long..

Charming Eastport
Kimberly's place is in a great location and is walkable to many pubs and restaurants, as well as to downtown Annapolis.
Family-friendly apartment rentals

Stylish apt w free gated parking, kitchen & patio
We had a wonderful stay at Lauren’s place and would highly recommend to anyone traveling to DC!

New Downtown Annapolis Condo With Free Parking
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.

Brand New Reno in Historic Dist w 2 Parking spots
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.

Rancho Relaxo! A Southwest styled Casita!
Abaad was very nice, proactive, communicative. The Airbnb was nice, as pictured. Would stay again.

Capts Qrtrs - Awesome downtown Annapolis location!
We had a great time once again staying here. It is just steps from the main gate of USNA and the downtown activities and restaurants. Caite was also responsive and very flexible with us and our needs.

Cozy Oxford Getaway
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!

Old Ellicott Condo | Historic mid-century home
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.

Unique, charming garden apartment
Great apartment! Sean’s apartment is very comfortable and tastefully decorated. It is completely quiet at night and the bed is good. There is a good vibe in the neighbourhood and the apartment is less than five minutes from a Green Line metro station that will take you directly to the best art museums in the city. Sean and his co-hosts are very helpful and responsive. I hope to come back to Washington one day and if that happens, I will definitely try to book Sean’s apartment again. Thank you Sean, Megan and Loren for all your helpfulness and a lovely stay!
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- Nationals Park
- The White House
- Betterton Beach
- National Mall
- Georgetown University
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- Hampden
- District Wharf
- Smithsonian National Museum of Natural History
- M&T Bank Stadium
- Sandy Point State Park
- Arlington National Cemetery
- Washington Monument
- Georgetown Waterfront Park
- Patterson Park
- National Air and Space Museum
- Great Falls Park
- National Harbor
- Smithsonian American Art Museum
- Lincoln Park
- Meridian Hill Park
- Congressional Country Club
- Quiet Waters Park