Family-friendly vacation rentals in Shelter Island Heights

We loved staying at this home - it was the perfect place for our group of ten. The outdoor space was definitely the highlight, with the pool & spa being our favorite part of the trip. The only thing to note is that we weren’t supplied quite enough toilet paper or paper towels, though I did not reach out for more - It was the last evening when we ran out and we were leaving early the next morning. The trash requirements were a surprise after booking, but going to the transfer station was easy enough, and it is listed on the house rules. Overall, an excellent stay and would absolutely return!

This was the most beautiful house in a private area in Wading River. It offers peace and tranquility and lives up to its name of Zen Retreat. It was exactly what we were seeking. Conveniently located near parks, farms and wineries I would definitely go back to Brian’s AirBNB. He was an excellent host and very responsive to our needs. Thank you Brian.

We love staying at this house! Beautiful, spacious, peaceful and great location (walking distance to water and town). Exactly the R&R we needed from the city. We'll be back!

Amazing! We really enjoyed our stay. Abby and David are extremely hospitable, responsive, and friendly hosts. The house is beautiful, clean, and well-located. The pool, hot tub, desk, and back garden are even larger and more beautiful in real life. We will definitely be back. Thank you Abby and David!

This house was the perfect place to enjoy a peaceful stay with our three young daughters. The grounds were in beautiful bloom during our time which made all of the outdoor time even more enjoyable. From the large yard, to the hot tub and the fire pit we enjoyed staying at the property as much as exploring the area. I appreciated the well equipped kitchen and the high quality bedding. Would love to return during the summer when the pool is open and the patios were all ready for the warm weather.

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 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.

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

Marta could not have been more accommodating! She was responsive and provided everything we needed. She even went the extra mile and insta cart-ed garbage bags and paper towels when we ran out. She could not have been a kinder host! We had the best weekend and would HIGHLY recommend staying at Marta’s place! We will definitely be back!

Look no further! The Beach Cottage is beautiful, immaculate, private, and all things one would hope a vacation getaway would entail. This location feels “off the grid” albeit close to modern amenities/stores. Hope to be back soon!

Wendy’s house is immaculate, tastefully decorated, very spacious and extremely comfortable. Her instructions were clear and her responsiveness immediate. We would absolutely consider staying there again.

We had a great time at Betsy's place. The home was beautiful and had an artistic charm, even better in person than in the photos. The location was perfect - close enough to town and yet felt private. We had a great time and would highly recommend this place. I'm looking forward to being back here in the future.

Cute and cozy home with lovely outdoor sitting area. Woke up to the sounds of the breeze and chirping birds! You can see the water from out the kitchen windows!

This unique apartment—formerly an art gallery—is definitely not your typical stay, and that’s what makes it so special. It has character and charm, with a fun, artsy vibe throughout. The kitchen was great, and the upstairs space was dreamy, with beautiful light and views of the trees. It was roomy enough for both my sister and me to stay comfortably. The location was perfect. Thanks for a lovely stay!

We were greeted by walking through the gate to the backyard in a rhododendron bush in full bloom. It was absolutely gorgeous. Everything from walking in the door to the Airbnb apartment to settling into the very comfortable bedding we had a really lovely stay, and I would definitely return for future trips. Michael helped us find a beach that didn’t require a local sticker that was perfect!

Cute and cozy place. Close to downtown Mystic. Definitely would stay again!

Laurie’s home was the perfect size for our girls weekend to celebrate the bride. The patio was extensive and comfortably fit all of us for a hibachi chef and dinner. It was a quick drive from the house to the wineries, which was fantastic.

Wonderful weekend stay. Charming.

Gabby’s apartment is exactly as described. It is in a great location. Very close to Stoney Brook Village. We enjoyed walking to get our morning coffee. The apartment was very well stocked and spotless. Gabby thought of everything we could have possibly needed. We hope to be back next year!

Absolutely loved our stay and the hospitality of the host, Kate. The house was very nice and the property is very private. Highly recommended! Thanks Kate!

We absolutely loved our stay at Milton & Megan's Montauk house! It was perfect for a group of 4 (2 couples) there for a 4 day trip. The house is very quiet & peaceful, with lots of outdoor space, but also very walkable to town. The house was super clean, and everything was very easy to find. The bedrooms had lots of closet space, the TV was easy to set up, and all the amenities listed on the website were accurate. We'd love to come back again and stay. Thanks!

Absolutely perfect. The house provides everything we needed for a great visit. Easy walk to the local beaches. Would definitely return if given the opportunity.

Ed was a great, communicative host, and the place was cozy for four of us during a week-long work trip!

Just had a wonderful stay at Robert’s place! The place was impeccably clean, and Robert was incredibly responsive and friendly throughout our visit. While the manor has a charmingly vintage vibe and could use a bit of modernization, we truly enjoyed our time there. The warmth of the atmosphere made it feel like a home away from home. We recommend for anyone looking for a cozy getaway!