Waterfront vacation rentals in Shelter Island

Really cute and clean place, so happy we stayed here! It was perfect little place for a getaway to relax, even in the winter months. Everything inside was up to date and it had everything we needed. It even looked better in real life than the photos. Highly recommend!

Great stay!! Beautiful ocean view and the complex itself is recently renovated, much more modern and luxe than expected!

This is our first AirBnB experience. Communication with KC in advance was great. The place is very nicely decorated, so we felt very comfortable right away. Our children liked the children's room very much and I liked the veranda. Our kids are very bright and loud and that's certainly a challenge for hosts. We are therefore glad that there were no complaints. The area is very nice and quiet. We will be happy to come back.

What a beautiful home. It is located in a park like setting, so peaceful and quiet. We were visiting family and the location was perfect for us. We would highly recommend this property and we will use it again ourselves.

What a great spot!! Away from the North Road so very quiet but close enough to zip to town. Robert the host is great. Very communicative however completely leaves you alone to enjoy your stay. But if you need anything he’s right there always. Comfy cozy room. Nice place to come home to after being out all day. I recommend!!

Just as expected. Our second time staying there. Recommend for an affordable stay in a great location!

My stay here was a perfect respite away from the hustle and bustle of everyday life. Tucked away in the dunes, very short walk to access the beach, quick ride into downtown Montauk, and private. Very beautiful place and I will definitely be back. Thank you again!

Amazing views! Beach. Glamping. Camp store and great pizza place.

Great location with amazing views. I can only imagine how lovely it would be in summer for a little getaway. .

The perfect house and location. We were visiting with 4 adults, a toddler, an infant, and two small dogs. The house came with everything you could possibly need to handle children. I was expecting the high chair and pack play but came to find so much more. The sound machine and bumper system for the bed were a great addition. Baby gate for the second floor. Toys. They even had extra stuff for the dogs including treats. The house itself was very clean and comfy. The yard was amazing. If it were warmer weather we would've taken advantage of the water. I cannot praise the house and host enough. If we come back in the warmer months this will be the first place we look to book.

This house is a gem! I came to stay a week in off season with my dog, Rollo. The location is breathtaking, right on the Long Island Sound. We had a great time exploring the beach, looking for all the biodiversity in the birds and sea creatures, watching the boats, and this place is relatively close to an airport so watching the planes land and take off was awsome as well. We came for privacy, and I expected the beach to be a little more private than it was due to my dog's reactivity. But the neighbors did not seem to have issues with us, and once you are close to the water, especially in low tide, the beach is pretty open for all the locals. Walking around, the locals all waved and said hello. Not too many restaurants close by, but the Lobster Shack down the road had good food! Would stay again! The deck alone was worth it!

We had a wonderful stay at Steve and Dorry’s place! The living room and kitchen is surprisingly spacious and feels so open & inviting because of the outdoor deck space and view of water. We hope to be back again!

As a native long islander I enjoy finding great properties I can bring my family to to take advantage of all long island has to offer. This was the DREAMIEST beach bungalow!! The bedroom with the two beds was just my favorite room especially since we visited off season. You cannot beat this location. I can't wait to book again during high season! Thanks for sharing your home with us !!

We had a lovely fall weekend stay at Paul’s place. The house and the water views are just as pictured. Convenient location allowed us a good home base to explore the north fork wine trail and local businesses. We did have one small plumbing issue during our stay however Paul was extremely responsive to ensure it did not affect our stay at all. It was a nice experience having such a responsive host. Overall our friend group had a great time and would return again.

John and his wife are excellent hosts. Their home is pristine with an abundance of amenities. The sunset on the bay is spectacular. I highly recommend. Thank you. Keith and Donna W.

The place is stunning. The views and being right on the beach is priceless. We stayed with two kids and a dog. Would want to buy the place that is how much we loved it! Everything is there as described and more. The piano was great for the kids! Chelsea is super helpful and nice. Finally again an AirBnB that feels like home.

Very clean and nicely decorated condo for our enjoyable weekend getaway. Would love to stay here again!

lovely 2 bedroom with gorgeous water views from two roomy terraces , nice to wake up to the breeze of the water and the unspoilt natural surroundings of the wild sound. Thomas was a great host and very responsive

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!

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.

My stay at Julie’s was wonderful, I was always able to message and get a quick response she was very accommodating. The view was beautiful and felt comfy like home. I will definitely be returning in the summer once it’s warmer !