Waterfront holiday rentals in Shelter Island Heights

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!

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.

We had a great week at this unit. Great view of the ocean. The staff was very helpful. The beach is a less than five minute walk across the street from the resort. The resort is about a 15 minute walk to the center of town. Highly recommend the sushi restaurant Bamboo at the Breakers next door. The walls are thin, but it didn’t take away from our week.

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!

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.

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!

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. ❤️

A fantastic beach house in a wonderful, quiet location, just a twenty-minute walk from all the town’s amenities and restaurants. The house itself offered substantial accommodation across both floors and was exactly as the owner described. Our only small recommendation would be for the owner to provide some blankets around the house. During our stay, the outside temperature dropped as low as 35°F, and although the house has heating, the open-plan living area could get a little chilly. Other than that, we all thoroughly enjoyed our stay and would certainly recommend this property to any family looking to stay in Niantic.

Had a wonderful time over Easter with my family and dog. The view was exquisite and the house very comfortable. Eileen was very responsive and even had hair dryers sent over. The house was very well equipped with lots of kitchen staple goods. Just be aware there is no microwave, but there is a very nice Breville toaster oven. Also, there is a large table outside for a group, but only a small table and counter seating in kitchen inside. We didn't have any issue since the weather was perfect for us to enjoy our Easter dinner outside. Overall, a beautiful home and only minutes from Greenport and wineries.

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.

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.

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!

This was the perfect last-minute getaway for my always on-the-go family in need of some quiet bonding time. The condo was simple and clean, the beach beautiful (even in the winter), and Alice and Gasper were very responsive. Would highly recommend!

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.