Waterfront vacation rentals in Shelter Island Heights

This was possibly the coolest Airbnb I have ever stayed in- the details of this place make you feel like you’re someplace truly special. Sam was amazingly responsive. The descriptions are accurate- that 3rd story spiral staircase is no joke - regardless, I was very comfortable and absolutely loved the setting. Will be back!

We thoroughly enjoyed our week at this charming home. The location truly is perfect - we walked over to the Seaport one day and took many walks into the downtown area for shopping, meals at amazingly good restaurants, ice cream, and bake shops. Anthony and Kelly were wonderful hosts - the home was just as described and their communication was clear and friendly- just what you want from hosts. We couldn't have asked for more and would be happy to stay here again.

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

Really impressed with the attentiveness of the staff. My only callout is expect to be surrounded by other guests, especially at the communal spaces outside – table, grill, etc. We overlapped with two different friend groups staying in a few of the properties, but everyone was really respectful and quiet. Just close quarters!

Stayed here for 2 nights, very well equipped place. Close to Amtrak station and walkable to the Main Street. Would love to be back at a different time of the year!

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.

Perfect house for a family/couple visit to the beach. It was great for my kids and I. We loved the space that the house offered and how close it was to the beach. Everyone was very pleasant that we spoke to. The house was clean, safe and felt like a home away from home.

Great place! It’s in a beautiful neighborhood. We couldnt walk into mystic but that’s because we had little kids with us. So peaceful and relaxing. Sitting in the back yard was a great way to unwind after fun filled action packed days. My little girl left her beloved teddy bear behind, fran found it, reached out and teddy is on his way home!! Thank you thank you.

We loved our stay! The private beach was perfect for our kiddos - far enough away from the water that they could play independently in the sand while we sat on the beautiful deck. The kitchen had all the items we needed (we even took a virtual cooking class while there). Dmitry was super responsive and helpful. The master bedroom was a beautiful place to watch the sunrise/sunset.

The place was absolutely beautiful, clean and had great amenities. The host was also very responsive and attentive to any questions we had to ask. Would come back in a heartbeat!

My family had a wonderful time at Robert’s home. The house was clean and cozy and the view of the water was peaceful. He was super communicative and friendly and check in/out was a breeze. The house is in a great area and super close to East Hampton, Amagansett, and Montauk. Highly recommend!

This house is in an idyllic, lovely location with a fabulous water view. It is spacious and well-supplied to have a comfortable stay. Enjoyed every minute of our visit.

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!

We thoroughly enjoyed our stay and would definitely book again ! Close to the many wineries and cute towns, and peaceful and comfortable to come back and relax at. We enjoyed the fire pit , the view from the dock of the changing tree colors and the flow of the kitchen. ❤️

The pictures don't do this place justice! The home itself is gorgeous and the view is stunning. The neighborhood is peaceful and it was perfect for me and four friends to stay the weekend.

The place was wonderful and absolutely close to the description. lot of details are added around the house including instructions making it very easy and good experience. would definitely recommend

Picture perfect! Newly updated accommodations with all the comforts of home. Extremely clean and very well managed. The view from this place is incredible. The perfect oasis in Montauk. Khrisna was extremely responsive and accommodating in our needs. Will definitely be back again!

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!

Absolutely wonderful stay and host. I've stayed at dozens of Airbnbs and this is one of my favorites! Doug's place is even better in person than the photos. We were a little nervous taking our first trip away with our baby, but it was extremely clean and comfortable, and Doug was so kind and responsive. The condo complex has a lovely boardwalk for taking walks, and the deck furniture was so comfortable to lounge in and take in the beautiful view. We hope to be back!

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.

We really enjoyed staying at Lynn’s place! Very clean and had a great view of the ocean from the deck. Lynn was very responsive and made the experience seamless. We would definitely stay with Lynn again.

Our second time renting a condo at Rough Riders in Montauk. Contrary to the name, there is nothing rough about this picturesque location with unobstructed views of the ocean, pier and wonderful wildlife everywhere. The condo we rented Sept 30 -Oct 2, 2023 has a well appointed kitchen with new amenities, including a pot filler faucet over the stove! Pristine/clean condo and lovely deck for lounging w/ book and coffee. The couch is very comfortable and the master bedroom has plenty of closet and bureau space for longer stays. The 2nd bedroom has bunkbeds so not ideal for two couples but perfect for small families. The television was a little tricky (if you bring tv-loving kids). Not walkable to downtown but theres at least one restaurant/bar just outside the entry to this gated community. Short drive to shops/restaurants in downtown Montauk. Horse lovers call Deep Hollow Ranch in advance to book truly memorable trail rides. Enjoy!!

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.