Family-friendly holiday 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 had a wonderful weekend. Great place to stay. Would recommend it highly.

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.

Patrick and Tracy were wonderful to rent from and the house was great. We had 5 adults and everyone slept comfortably. The patio was a great experience with the pool, hot tub and great outdoor seating. We loved the area and would return in a heartbeat if the dates are open for next year’s trip.

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!!

This spot was a great find. Hadn't been to Shelter Island before. I found the location super convenient. Literally every place I went was 5 mins on GPS from her house. She was very clear about everything, responsive to emails, and everything was as described, however the pictures don't do it justice. Beautiful home and pool, people came to clean the pool early one morning during the stay and were not disruptive at all. There were beach chairs, umbrellas, pool floaties, games, netflix, literally everything you could want or need. Loved our stay!

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!

This place checked all the boxes. Very clean and comfortable home and a short uber ride to downtown Sag Harbor. Nice big yard for relaxing after a long day on the boat. Will definitely stay here again. Great host and a great place

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!

We loved our stay! It was one of the coolest Airbnb stays our family has enjoyed. Lots of art and ambiance while also being very comfortable with all the amenities you could need. It is an open space (the bedroom walls don’t extend all the way to the ceiling), which didn’t bother us at all but something to be aware of. Thank you Pam!

We had a great stay! The host was incredibly responsive, helpful, and proactive in communicating with us throughout the process. She went above and beyond to accommodate a request for check-in flexibility, which we really appreciated. The space itself was lovely and well-appointed. Overall, a wonderful experience and would definitely stay again!

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!

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.

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!

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 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!

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.

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!