Family-friendly vacation rentals in Shelter Island

This is the 2nd Thanksgiving weekend we spent at Deeanna's. Her home is beautiful, comfortable and each detail is thought though in the best way. Deeanna went above and beyond to accommodate my family and we are so grateful to her. The kitchen is perfection and the bedrooms are lovely and comfortable. The scenery and views are breathtaking. Overall, this home is a total gem. Thank you, Deeanna! We hope to come back next year!

This getaway was very last minute and there was huge importance on it because I needed some time away and because I had never booked an Airbnb before. I wanted to make sure that my family and I were able to be someplace peaceful and have a really good time and Brian’s home provided just that. The stay was so much more than we expected and Brian was absolutely amazing. He’s super responsive and accommodating. Hoping to stay here again in the near future!

Fantastic stay/fantastic hosts! My adult children and I spent a great weekend hosted by David and Abby. Their place was perfect for us and very comfortable. David reached out and described check in and proactively answered any questions we would have had. We were there in cold weather but I will earmark it for a warm weather stay as it has so many appealing summer amenities! We will stay again for sure.

Six of us flew in from all over the world to have a friend reunion here since it was the most convenient location for us all to meet up. The house was great for this occasion in that it is cozy, and conveniently located. Our favorite spot in the house was the sunroom with the wood burning stove since the weather was mostly gray and on the chilly side. The kitchen was the next most popular spot and was well equipped, better than most places actually. David and Claire provided clear check in and checkout guidance and were proactive in their communication with us. Thank you!

We had a wonderful stay at Jennifer’s place. It was.l beautiful, immaculate, and incredibly well equipped—especially for kids with the plethora of games and toys. Jennifer was responsive and a great host. The house is on a serene, dead-end street, and outdoor area is perfect for kids.

Great getaway for our family of four. Many things to do both on sunny days enjoying the yard to play sports with the kids and also rainy days with plenty of games, shuffleboard, the hot tub and theatre downstairs which our eldest loved to watch movies. Josh was always very responsive and everything was very smooth

We loved our stay at Chandra’s place, it was peaceful, super comfy and was close to everything we needed. It was great to enjoy a few runs locally and come back to the private garden and hot tub in the evening. The property was beautiful and well stocked with towels, soft bedding and kitchen equipment. I’d love to come back again in the future

This home is top notch!! Esther is truly amazing and everything was excellent. The kitchen is amazing, the basement play area was awesome and the rooms were perfect! I will be staying here again!

This place is perfect for a large group with lots of queen size beds. Easy walk to Ocean beach.

We absolutely loved our quick getaway from the city at Kate’s lovely home. It is hard to articulate in words just how beautiful of a home and location this was. It was truly magical. We were very comfortable as a family traveling with young children. Despite the weather being a bit chilly, we had a wonderful time soaking the views and discovering “treasures” by the water. We cannot wait to come back again soon.

Ed was great at communicating, house was everything we could have asked for. Would definitely book again!

We had a wonderful stay at George’s. The unit is exactly as described, don’t be deterred by the adherence to the house, it’s completely private. It’s at a great location for north fork explorations and the amount of towels was outstanding!

This was a great find! I booked this Airbnb for myself and 4 other girls and there was plenty of room and space for us to hangout, sleep, and get ready. Walkable to town. Extremely clean and had all the amenities you would need for a short weekend getaway. Marianne and Steven were very responsive whenever I had a question. I would totally book this Airbnb again!

This place is amazing. The beach is a 3 minute walk through the dunes. The beach itself is in an area with less density. The space of the studio itself is bigger than comes through in the photos with high ceilings and perfect set up for a peaceful and relaxing beach get-away. Comfortable bed.

Wonderful time staying at Milton and Megan's. The location was perfect and the home had everything we needed and more to work remotely for the week. Thank you!

We had a wonderful stay at Steffen & Sara's charming bungalow! The location was incredibly convenient, check in was a breeze, and the house was comfortable, well-appointed, and inviting. The house was meticulously clean and well-maintained. Steffen & Sara were incredibly responsive and accommodating, making sure we had everything we needed for a great stay. We would absolutely stay here again and highly recommend it to anyone looking for a great place to stay in the area!

We had a wonderful stay. Cute and comfortable house in an amazing location. Very comfortable for a family of 4.

Michael was a great host, friendly, flexible and helpful. The house is beautiful and has all the amenities you would expect. We loved staying there and would definitely like to stay again.

Loved the place! Clean and comfortable. Had everything we needed. Perfect location near family for the Thanksgiving holiday. The main street w/ restaurants & shops was just 10 min away. Robert and Chris were very responsive and provided detailed instructions and many recs for the village. Very kind! 10/10

The house is beautiful, looks like photos. Stephen is a great host! Overall great stay, could not recommend more!

We loved our stay here. The house was sparkling clean and the yard was big and beautiful. Can only imagine the vibes here during the summertime when the pool is open!

We absolutely loved staying at Christine’s beautiful home! The place was immaculate, and we particularly enjoyed the pool and fire pit. The location was perfect—situated in a quiet neighborhood, close to great restaurants, and within walking distance of the water. Christine was an amazing host, letting us check in early and check out late. She also texted to make sure we had everything we needed and were enjoying our stay. She even stopped by to share some great recommendations and ensure we knew how to use the house and pool code. We had a fantastic experience and would highly recommend this Airbnb to anyone looking for a relaxing and enjoyable stay!

We had a lovely stay at Eric's home. The home exceeded our expectations and we felt right at home. The decor was warm and inviting. Everything you could possibly need was in the stunning, modern kitchen. The beds were all comfortable and we slept very well. The property was very peaceful. We enjoyed seeing deer, turkeys and hawks each day. The fixtures in the home were modern, clean and high-end. It was great being so close to Greenport with it's wonderful restaurants and shops. We can't wait to return.

Such a charming and cozy house, the photos don’t do it justice! Clean, well appointed, and comfortable. We had everything we needed and felt right at home. From the house we were able to walk to the beach (about 30-40 minutes along a safe route with sidewalks). The town is a quick 5 minute drive. We enjoyed the pool and the beautiful lawn. Ed made the whole experience seamless by being super responsive and helpful whenever we had a question.