Holiday rentals with a pool in Kent Island

Beautiful location. Cottage was nice and cozy.

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!

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.

This was one of the most well equipped houses I have ever stayed in. The hosts were very easy to communicate with and responded quickly to each contact. I highly recommend this place!!

This home gave us something we hadn’t experienced before: a vacation with two small children that actually felt like a vacation! From the moment we arrived, we were blown away by how perfectly suited the home is for families with young kids. The pool has a shallow platform area that our toddlers could safely enjoy, and the expansive, beautifully maintained yard gave them plenty of space to run and play freely along with a swing and hammock. Inside, the house is just as exceptional. The layout is thoughtfully designed, with a separate bedroom wing that allowed us to put the kids to bed and then relax in the evenings without worrying about noise. Every detail felt intentional and welcoming, and the water views were absolutely stunning. The home is just a short drive from the charming town of St. Michael’s, which we loved exploring. This trip was such a joy for our entire family, and we’re already talking about when we can come back. Highly, highly recommend!

This place is an absolute gem. We’ve stayed in everything from sleek modern homes to charming older properties, and this one truly stands out. Although built in the early ’90s, it has a unique colonial charm that feels timeless. The bedrooms and bathrooms were spotless and comfortable, with plenty of drawer and closet space for everyone. While it’s listed as a four-bedroom, there’s an additional upstairs room perfect for an air mattress, making it easy to accommodate up to 10 guests. What really drew us here was the peaceful setting—and it didn’t disappoint. The pool sits in front of the house, while the back opens to serene water views. Both areas offer spacious, covered and open seating to relax, rain or shine. In fact, we spent our first rainy evening on the covered back porch, just soaking in the view. We also brought our dogs, who absolutely loved having so much room to explore. The fully fenced yard gave us peace of mind, which made the stay even more relaxing. The hosts were

Our family of 3 had an amazing vacation on our 4 day stay. It was so peaceful and relaxing. The place was exceptionally clean and organized with everything needed. Amazing views on the water and pool was great. We had some rainy weather but still managed enough dry time to enjoy the pool and outdoors

Our group of 8 had a wonderful, relaxing time in the peaceful, natural environment. The property is at the edge of the Chester River and we were delighted to see ducks, peacocks, a tiny turtle and fish. Be prepared to encounter a few insects and spiders outside; we did not see mosquitos. We enjoyed using the grill, pool, hot tub and kayaks. We wanted to use the fire pit, but ran out of time. Inside the house was clean, comfortable and good for group cooking, socializing and movie-watching on the ground floor. The beds were also comfortable (more soft than firm). The children liked the playroom. The photos accurately reflect the spaces. The host was communicative. We would love to stay here again.

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.

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!

I definitely loved this home soooo spotless felt right at home. You might hear people walking here and there BUT it’s not an all the time thing, other than that it’s so peaceful. Kitchen is beautiful and has all the spices you kinda need if you wanna cook, bed was sooooooo comfortable and the living room was so inviting. It’s close to food spots banks grocery stores, etc. I’m definitely booking again.

My family & I booked for three nights. Thought it was a beautiful and private little area, and just a couple steps away from the beach and a pool. Very quiet and away from noise which was a plus. The house itself was lovely and mostly clean. There were board games available and my kids had a fun time playing with them. We enjoyed barbecuing using the grill provided on the balcony which was nice as well. A plenty of towels and anything you need in the kitchen! Other than a full trash bag left over in the kitchen, finding some clothing items from other guests (I’m assuming) in drawers, and the keurig having what looked like mold inside. Pretty small things when looking at the big picture though. Will most likely come again & we enjoyed our stay!

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.

Great place with nice amenities! We enjoyed our stay, and the host was very communicative.

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.