Holiday rentals with outdoor seating in Kent Island

This was our second time staying at Kimberly’s home, and it was just as magical as we remembered. The views of the water are absolutely stunning—whether you’re enjoying your morning coffee or winding down in the evening, it’s hard to look away. The location is perfect: peaceful but just a short walk to shops and restaurants. We also really appreciated the Peloton and treadmill—such a bonus for staying active during our trip. Everything was spotless and thoughtfully prepared. Honestly, we didn’t want to leave. Already looking forward to our next visit!

The property, location, house set-up, and communications from the management during our 6 day stay was amazing. Literally the best low-key, relaxing experience I have ever had in recent memory. The house has everything you need for a great peaceful stay, especially if you are just hanging with a small group of close friends. Cooking is particularly awesome, as this property has a great wide open kitchen. The grounds are beautiful. We spent most of our time on the main floor in the kitchen and then on the long beautiful dock where we did some fishing and first time crabbing just for fun. The town nearby and neighborhood is so nice. Not far from Annapolis, MD at all if you want to visit. But honestly, the property alone is so nice to just to stay in and just relax. Great space with some homey accommodations. Big shout outs to one of the property management team members, Melissa. She was so very helpful. Will be back again next year!

Beautiful home steps away from all the shops and restaurants in St. Michaels. We walked everywhere and had a fantastic time. I’d love to come back and stay here again!

Laurie’s place was just liked it is described. It’s located in a beautiful area and walkable to all the attractions in Annapolis Maryland. I would recommend it and I would stay there again if ever back in Annapolis! Thanks for wonderful stay!

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.

Scott and Melinda's place was perfect for a peaceful getaway for our family of 5. The water was so nice to wake up to and fall asleep hearing the water move by! The thought of all the basic needs and had everything easily accessible from fresh eggs from their chickens, a great variety of coffee pods and creamer, and all the other small needs that come up while staying in an airbnb. This was great since it is off the beaten path. If you are looking for some peaceful family time or a secluded retreat with friends, this is a perfect place!

This house was perfect for our stay in MD. Our family of six was very comfortable here and our kids loved the pool and spa. The house is clean, cute and very cozy. Tanya was very quick to respond and great to work with!

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.

I stayed in DC over 20 times in the past 20 years. I have to say Chris’s place was at the top of the list. I picked it because we were going to the Smithsonian zoo. Which was only a 8 minute walk to the Harvard walk in gate. The best restaurant within walking distance was ll Supremo Italian food. Very good for such a small place

Very responsive host. The side yard is very nice for people with dogs that travel. Location is very nice but DC traffic during rush hour can be rough but this can be planned for. Would stay again.

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

Highly recommend Ann’s place! We traveled with our toddler, and it was perfect for him. They supplied a pack and play and tons of board books. My only thing to note is that the walkway to the space is not paved so be aware with small children and suitcases.

This space is absolutely stunning. The natural light, the calm atmosphere, and the beautiful design all made it feel like a peaceful retreat. The gas fireplace was my favorite feature. It brought so much warmth and comfort to the space. What really impressed me was how well it is set up for longer stays. Everything was thoughtfully included, from the efficient washer and dryer to the kitchen area, steamer, and other essentials that made my business trip easy. The hosts were kind, attentive, and made everything feel smooth. I felt right at home and definitely recommend this place.

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.

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

I had a wonderful stay at Jill’s place in Saint Michaels. The flat was exactly as pictured—immaculately clean, thoughtfully arranged, and exceedingly cozy. It made for the perfect home base. Jill was a fantastic host—very responsive and full of great local recommendations for things to do and places to eat around town. I would absolutely stay here again and hope to have the chance to do so in the future!

We had a wonderful stay at Lauren’s place and would highly recommend to anyone traveling to DC!

Perfect location for exploring Annapolis attractions via walking including Naval Academy and downtown. A bonus for me, all areas were wheelchair accessible (except balcony). Very clean and well maintained! Bed was super comfy!

Celia’s place is one of those AirBnbs that just shine. It is a beautiful, private, comfortable and spacious apartment in a central but very quiet neighbourhood. And the hosts really have thought of everything. From coffee and milk through to gowns in the bedroom, it is a bit like staying in a five star hotel. Thanks so much for a great stay.

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!

very nice place and very well situated. It is clean, decorated with taste (lovely plants) and has everything you need! beds are also very comfortable. I definitely recommend!

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.

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!

My husband and I came for the Nationals vs Cubs series and the location couldn’t have been better! The house was spotlessly clean, well-maintained, and exactly as described in the listing. Israel was incredibly responsive and helpful, always quick to answer any questions and made check in and check out smooth and hassle free! You can really tell he cares about his guests’ experience. Highly recommend this place for anyone looking for a comfortable and conveniently located stay!