Vacation rentals with a kayak in Shelter Island

We try and rent this place every time we come to the area. It is immaculate, well appointed and the hosts are very responsive. The property is also beautiful - with a swing set, giant yard and fire pit and it’s a great set-up for families with dogs and kids. I should mention for non kid and dog people that the level of cleanliness is incredible and the place is beautiful so don’t shy away if you don’t have kids or pets!!

Amazing place, super accommodating, and so understanding. Experience was absolutely amazing.

We thoroughly enjoyed our stay and would definitely book again ! Close to the many wineries and cute towns, and peaceful and comfortable to come back and relax at. We enjoyed the fire pit , the view from the dock of the changing tree colors and the flow of the kitchen. ❤️

Petra’s house is in the most beautiful spot on a small lake and a stones throw from the beach. This was our second year there and we hope to be back. The house is stocked with everything you need to feel comfortable including great bath products, kitchen, equipment, and toys and books. I never felt uncomfortable in her house. This was a wonderful family week in heaven.

I would highly recommend Melissa's place in Jamesport. It was a great location with room to enjoy with some family members including children. It was perfect with some toys and a big outdoor area (and a private beach!) for us all to spend some time together while visiting family in the area. Melissa was accommodating and clear in her directions and gave us a warm welcome with a greeting basket, information about the area and coffee! The location is lovely and everything about the house was fun and comfortable. Thanks!

Frank went out of his way to resolve an unpredictable issue caused by harsh weather, including driving hours in the middle of the night to assist. The house is beautiful and the place very peaceful.

The house was as advertised and well appointed and comfortable. I would stay again. Our family had a very nice memorable long weekend.

This house was very good for me and my friends and we would love to go back!

Had a great weekend at the cottage! Meredith was so great letting us check in early and was super helpful and responsive. The cottage is gorgeous and has everything you need. Loved it! Thank you!

Prachtig gelegen vakantiehuis op loopafstand van strand. Fijn huis en fijne omgeving!

My adult daughters and I thoroughly enjoyed our stay in this peaceful cottage! The cottage was cozy, comfortable, and just the right size for the three of us. The house and kitchen had all the essentials and we enjoyed the treats and complimentary food that Gail provided. We relaxed and strolled down to Indian Cove and Barbra Pine Memorial beaches. Overall, we had a fantastic stay and highly recommend!

We lived our stay at Carey’s place and plan to come back next year. Amazing location if you want to relax and take a few days away from the city. The house is very cozy and comfortable with a great backyard facing the water. Thanks Carey!!

We had an amazing stay with Sean and Jenny. The property is perfect for a peaceful getaway from the stresses of daily life- unique location, impeccable views, spotless and well furnished house, we were able to unplug and enjoy some nice quality time. Sean is a gracious host, offered lots of local recommendations as well as details of the house that were very helpful. Was responsive for questions and easy to communicate with. Hope to be back one day!

The house was so peaceful and quiet. The deer were just walking around and calming to watch! The backyard is better than the pictures and would stay there again! My only issue was with the lack of privacy in the house. The doors are similar to shutters to allow airflow, but you could here everyone in all the rooms. Not a huge deal unless you have loud kids!

Thank you !! We enjoyed our stay. The home is lovely and the area was so convenient to all ! The airport is 7 minutes away. Def would stay here again. Thanks again

Christie was an excellent host! Her house was warm and welcoming, with a wonderful outdoor space. It was very clean and well stocked with everything you might need for your stay. The location was great, we loved having a private beach just steps away. All the neighbors we met were so friendly and kind. This property was perfect for our family of four. We highly recommend it, especially if you are looking for a calm, peaceful beach vacation. Wish we could have stayed longer. Would definitely love to stay here again!