Kid-friendly holiday rentals in Shelter Island Heights

The property is well located in a very private setting with a large yard, and had space to comfortably accommodate our party of six adults, two children, and two infants. The home is well furnished, nicely decorated, immaculate, and very child friendly. Chelsea was a great host and provided helpful recommendations before and during our visit. Overall, our family group had a wonderful time during our four-night visit to Westhampton.

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

We had a great stay in this lovely home. It was cute, clean and included everything we needed…plus some extras like a bottle of chilled rose upon arrival! I highly recommend this place for families or anyone looking for a quiet, stylish place to enjoy some time on Montauk.

Paula's house was absolutely perfect for our needs. We had 7 adult females looking for a comfortable space to relax and unwind for an evening, and that's certainly what Paula's home provided. It was clean and cozy, and had a TON of sleeping space - everyone got their own bed (the pool house was an especially fun place to sleep!). While the main living space was pretty small, it was designed and laid out really well. Would definitely return - preferably in the summer when we could enjoy the beautiful backyard and pool! Thank you, Paula!

We came back to stay for a second time and hope to be back for many more! The place is exactly as advertised, beautiful, and an easy walk into town. Marianne and Stephen were super flexible with a few requests we had around the stay and so easy to communicate with. Greenport is the best and this home is amazing - you won’t regret booking here!

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

We had a lovely time at Bella’s Beach house! We had plenty of necessities provided including paper products and the kitchen had a great coffee bar and selection of hot teas. Coffee and condiments provided even some staples in the pantry! The space was large and confortable! It was just perfect for having a relaxing stay!

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.

We had a great weekend at Mary’s. The apartment felt cozy and was well stocked with complimentary coffee and snacks. Would love to stay again if I’m ever back in Westerly!

Very beautiful place the host was very responsive very polite This place felt right at home. The balcony was beautiful. The kitchen was beautiful. Everything about the place was beautiful. I would so love to stay here again. The aura and energy was very positive very vintage.

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.

We just completed a wonderful five nights stay at Kevin‘s apartment. Everything was perfect. Located in a quiet neighborhood. We enjoyed walking to dinner at a local Irish pub. There are clean apartments, and then there is Kevin‘s apartment. The place was literally spotless. Kevin was great at communication. Clear instructions and he even accommodated our request to extend the stay one night I highly recommend this apartment as a comfortable and enjoyable home away from home.

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!!

This is a great place to stay to explore Mystic. It was comfortable and walkable to downtown. I traveled with three teenagers, and we were able to have privacy and spend time together in this space. Highly recommend!

I had the pleasure of staying at Rosaria’s apartment for two months, and it was an amazing experience. The place was spotless, well-equipped, and had everything I needed for a comfortable stay. Rosaria herself was incredibly kind and helpful, always making sure everything was perfect. I highly recommend staying here to anyone looking for a great place. Thank you, Rosaria!

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.

This was a great find for us. The apartment matches the description and was spotless when we arrived. The bed in particular was amazingly comfortable as was the couch. The interior is free from clutter and the kitchen included a fair amount of spices, cutlery, pots, etc. Communication was great as well. The location provides very easy access to downtown Mystic and its many restaurants and bars. We enjoyed our stay and would definitely consider returning here next time we are staying in Mystic.

Great location! Easily accessible to the beach either via driving or walking. Quiet area. It was a nice place to stay for the weekend.

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

Comfy, clean and peaceful. Would definitely go back.

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!

Irinas place was exactly as she described. She answered all inquiries in a timely manner. We will definitely be back.

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!