Kid-friendly vacation rentals in Shelter Island

Staying at Amy's place was perfect for my friends and I while we're out on the North Fork for a wedding. Amy was very responsive with any questions we had. We were all very comfortable in the main living area as well as our bedrooms. The house was conveniently located to the wedding venue and my friends were also very happy that it was located near some pickleball courts. Thank you Amy for a wonderful stay.

I cannot say enough good things about this place! Myself and 5 others were working in the area and needed a place to stay for two months and we could not have found a better home. It is in an unbelievable location walking distance to the beach, safe, private and truly was a summer we will never forget. Cannot say enough good things about Mariah and her family as well. Can only hope to be back in the future and I would give 100 stars if I could! Thank you thank you thank you ❤️🫶🏻

Aida’s house is very nice place to stay for a getaway in the Hamptons. Amazing outdoor area. Great for traveling with kids. Aida is a great host!

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

Fantastic stay/fantastic hosts! My adult children and I spent a great weekend hosted by David and Abby. Their place was perfect for us and very comfortable. David reached out and described check in and proactively answered any questions we would have had. We were there in cold weather but I will earmark it for a warm weather stay as it has so many appealing summer amenities! We will stay again for sure.

It was wonderful stay and I’d go back anytime

This was my second time staying here, and probably won’t be the last. A perfectly wonderful Hamptons home, with a beachy, rustic charm. It’s close to all, yet on a quiet street with a great backyard. David is a fantastic host, everything was spelled out clearly and the home was spotless.

Such a great house for a group! Well kept and very accommodating. Will definitely be back

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

Great spot! Very walkable. It's also a great layout if traveling with small children - there is a separate meditation room upstairs that was perfect for setting up our travel cribs. Would stay again!

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!

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

I had the best stay, it’s about 15 min. Or a little more if you’re not in a hurry to down town Sag Harbor and all the super cute shops and wonderful restaurants… and of course all the Galleries… Such a cute place and the bed was overly comfy… The host was so accommodating and helpful, I definitely recommend this place!!!

Lovely, clean, comfortable, well-designed space. Hosts are friendly, responsive, and respectful of guests’ privacy. Would stay again!

Great stay at a great location

Great place ideally located next to town and the view is amazing. highly recommend in particular for short term stay.

John and Cathy are amazing hosts. This was our second consecutive summer stay in their condo and it does not disappoint. The place and the amenities they provide are amazing and they are a wonderful couple who respects your privacy but are there for anything you need. I recommend anyone to stay here and know they would want to return. Thank you John and Cathy for making our second summer with you a fantastic vacation!

We very much enjoyed our stay at the Cliffside for our wedding weekend! Alice was very flexible with us, which we appreciated because getting married is chaotic enough LOL. Would highly recommend staying here. The unit was spotless and had a wonderful view. We could not have asked for a better stay!

We had an amazing stay! We stayed off peak season, although alot was closed we felt right at home and were more than happy to spend family time at this condo! The views were stunning, and the condo was immaculate. We were close to everything and was still within very reasonable driving distance to the surrounding towns. Julie was a pleasure to work with and was always very responsive and accomadating throughout the process. Hoping to stay again next year!

Such a beautiful condo by the water! Too bad we stayed in November, we would have enjoyed the terrace way more! Mia was so responsive and helpful with my questions prior to the weekend at her place.

If we don't give a good review, can we keep this to ourselves?! Patti was a perfect host; the views were fantastic, whether from the outdoor porch or inside through the French doors looking out on the water. Access to the small beach and pool were excellent and we were close to several good restaurants (many of which Patti suggested, including some on the water) for take-out during the pandemic. Wifi was great and everything was very clean and as advertised. We generally fly for vacations and long weekends but had to stay closer to home this year and this was a perfect choice.

Had a wonderful stay with my family. Clean, comfortable, great location. Good communication. Had a little trouble with the front door first day but someone was available quickly to help. A+

Great place to stay in Sag Harbor!

The place was perfect nice and clean what I like the best is the it was close to the beach to go for a walk.