Family-friendly holiday rentals in Shelter Island Heights

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!

Had an absolutely wonderful stay! Location is perfect and Jaime was incredibly friendly throughout!! He let me know that they had everything we would need.. but as a self-described obsessive packer I didnt listen. He wasn't kiding! They had beach chairs, umbrellas, and everything else you need for the perfect beach day. I brought an entire wagon of stuff and used one bag. It really is an awesome little find!!

We had a fabulous time! Can't wait to come back. Was equally perfect for two toddlers as it was for four adults! Beautiful property, amazing hot tub, comfortable beds, great kitchen... everything was lovely.

Cozy and pretty home, all ready for a chill weekend. Cindy is super nice and easy to work with. Very generous too. The 2 pups loved the fenced in yards. Kitchen/dining room space is big and bright and awesome to hang out or read in the corner nook. I am sure the backyard and pool would be great in summer. Beds were comfortable. Thank you Cindy!

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.

This house served our family very well for a multi-month stay. The house and property are just like the photos and all the amenities were great to have. Would recommend staying here if you are looking for a quiet place near the water in East Hampton. Petra was always very responsive with anything we needed and was an excellent host.

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

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.

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 two day stay at Roger and Amy’s place. It was fantastic- such a beautiful, inviting home. Our kids had a blast in the heated pool- we could barely get them to come out despite it being under 60 degrees out! The kitchen was stocked with more than just kitchen basics- the spice cabinet had soo many different choices ! It was probably the most perfect AirBnb experience I’ve had and we travel plenty.

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!

Tricia and her husband were so lovely! They were super responsive, kind, friendly, and went above and beyond to make us feel welcome. The cottage was super cozy, clean, and pet friendly. Our dogs loved the private outdoor space. The location was also excellent - a short drive to town in Southampton and Westhampton. Would highly recommend and will definitely be booking again in the future!

Perfect little backyard for our pups, great sunrise from the porch overlooking the water from across the street. Was exactly what we needed for a little weekend getaway.

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

Great place to stay. There are occasional noises upstairs but area is nice and weight. Unit was very clean as well.

We had an amazing stay at Michael’s Airbnb this past weekend! The space was exactly as described—clean, cozy, and well-equipped with everything we needed. Michael was a fantastic host: super responsive, thoughtful, and made us feel completely at home. The location was perfect for a relaxing getaway, and the setting was even more beautiful in person. Would absolutely stay here again—thank you for a wonderful experience, Michael!

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.

We had a fun weekend at Abigail 's place. The house is in a quiet cul de sac - exactly what we were looking for. There is a private beach a 15 min walk away that the kids loved. Host was very responsive and house was clean and stocked. thanks for having us!