Kid-friendly holiday rentals in Shelter Island Heights

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

We had an INCREDIBLE stay! We went for my sisters bachelorette party and it was perfect. It made me want to book again in the summer! I was initially worried about space, but everyone fit perfectly. Paula was very accessible and easy to work with:) 10/10 recommend.

Don't walk run and book your stay here. I mean wow! Mary's place is unbelievably beautiful, clean, comfortable, spacious, peaceful and very private. She has everything you need and then some. I'm so glad I picked this place to spend my 50th. You will not regret it. Thank You Mary🫶🏻

Very nice setup for two couples, a baby, and a dog - could spread out with bedrooms and full bathrooms on each floor. Comfortable space with amenities you'd want while traveling with a dog and a baby (fenced in yard, laundry, etc). Very walkable to all the shops & restaurants in town, and easy drives to wineries & breweries. The only drawback was that it was close to a fire station and the sirens woke the baby from a nap.

We had an amazing stay at Alissa and Danny’s house! The location is perfect—convenient to everything we needed, yet peaceful and relaxing. The house is carefully designed with families in mind, especially with kids. It has everything you could possibly need for young children, from toys to safety features, making it so easy to enjoy our time there. We were so impressed that we’ve already booked again for our next trip! Highly recommend for any family looking for a comfortable, family-friendly! Mine Gur

Our stay at Bella's Beach Cottage was very pleasant. Rosemary is a wonderful host who had clear, easy to understand instructions. The cottage is laid back and casual, so we felt right at home. It was well stocked with lots of amenities (including a piano!) We very much enjoyed our stay and hope to return some time.

Dorina was a terrific host. She responded in a very timely manner to our questions as we prepared for our vacation. The location was a mere 5 minute walk to the beach and on rainy days, you didn't mind being inside since the layout is open and sunny. When I mentioned that a family member had asthma, Dorina offered and arranged to have an air purifier placed in the house, which was very thoughtful. The house is extremely clean (something which is very important to me) and was a wonderful venue for us to host our family.

Enjoyed our stay. Host let us check in early. Very clean

Hi all! Hate to say it but this was a little slice of heaven for me - everything I needed and more to make my stay super comfortable and EASY! Great location for me and everything was clean and in order - I will TOTALLY stay here again if I have the chance and you all don't book it all up on me! :) Thanks Jennifer - great hostess!

Enjoyed our stay and will come back! Thanks.

There are a lot a reasons to use Airbnb, and one is that you can stay in the most interesting places. That's the reason to stay at the Ludington mansion. Incredible property. If you have any interest in history or architecture, this is your place. We stayed in the 3rd floor suite; of course, it's not a good choice if you can't manage the stairs, but since that was not a problem for us, we loved it. The space was as described: full of character and immaculately clean (if not always new). It was nice having two full baths. The next-door church bells didn't bother us. I can't think of anything we needed that wasn't there. We appreciated the host's suggestion for where to have dinner and were not disappointed. We ended the evening by streaming the (admittedly cheesy) Hallmark Christmas movie filmed on the property and spotting furnishings that were in our suite. We wished we could have stayed longer instead of just over-nighting while on the drive from Maine to NC.

Our 3 time staying at Amanda’s home. Beautiful and spacious within walking distance to village. Looking forward to coming back next year!

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!!

Michael is such a courteous, considerate and generous host. We have stayed many, many times and it feels like a second home. I highly recommend this cozy, clean apartment. Micheal goes out of his way to make sure you are taken care of. Best host! Truly!

Joanne’s place is a great cozy and spacious one bedroom apartment that my husband and I enjoyed relaxing at. We found it so comfortable we decided to stay an extra night since we are off from work this week and wanted to just chill out there a bit longer. Joanne was always responsive and easily accepted the reservation change to stay an extra day which was nice of her. I would definitely recommend her place and stay again in the future.

We had a wonderful stay at Paris' place. Easy check-in, very clean, great location. We'd certainly come back

A brief stay but a great stay. It was offseason but we got lucky with sunny October weather. The stay was less than a 5 minute drive from the main village with tons of shops, cafes, etc.. the room itself had a beautiful ocean view and was very clean and comfy. Nice shower, comfy beds, plenty of linens and towels provided. Parking included. Overall a very nice stay.

Camila was a great host, very responsive and always helpful. The apartment was clean, tidy and cosy and made us feel at home very quickly. Location was good, walkable distance to New Haven Green and its surroundings. All in all, we enjoyed our stay very much and would recommend Camila’s place to anyone planing to spend some time in New Haven.

It was really beautiful inside & the view outside was really pretty! the historic mystic sign is right in the backyard! we came in the winter & it was nice, i can only imagine what summer is like!

Lovely stay in greenport! Short drive from major north fork activities. Can imagine its even better during the busy season!

This stay was even nicer than its pictures. Went during “off season”, so many places were closed in the area. However, the actual airbnb made up for that. It was beautiful, peaceful, and quiet. We had our own ocean view and easy beach access.

Overall relaxing stay and trip to Greenport. Sherri is very communicative and her instructions and listing is clear and accurate. The condo is well decorated and clean and has everything you need for a nice weekend. One thing to note- we were aware check in is between 3 and 5 pm based on the listing (wound up being around 4) but it would be nice for it to be earlier. Still 5 stars though!

Incredible stay at #19 The Bridge the whole 3rd floor with two comfy family inviting areas to hang out and enjoy, large tv in every space, 4 great bedrooms with new mattress so comfy, luggage holder and greeted with fresh towels in every bedroom and great sound machines, chargers and ceiling fans in each bedroom. Bathroom one with jet tub, shower and bidet, beautiful tile and clean! Kitchen had all the plates, glasses and utensils, pots and pans needed and an awesome coffee station we enjoyed cooking breakfast every morning and then enjoyed at the family table large enough for 10-people if needed and a high chair provided for our grand baby! Rooftop outside table was great for enjoying the gorgeous view of beautiful Old Colony Beach! Short block walk to private Old Colony Beach made for an amazing family vacation! We can’t wait to come back and make this an annual stay. Thank you Peter for making #19 our new vacation spot.

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!