Beachfront holiday rental in Shelter Island

Overall a very nice and pleasant stay. The house is very nice, super nicely decorated and amazing views. Really worth staying here.

“A Wonderful Stay!” I had such a pleasant experience at this Airbnb! The space was clean, cozy, and exactly as described. The host was incredibly welcoming and attentive, making sure I had everything I needed for a comfortable stay. The location was perfect—quiet and peaceful, yet close to everything I needed. I especially appreciated the thoughtful touches throughout the space, which made it feel like home. I wouldn’t hesitate to book again—highly recommend! Feel free to customize it with any specific details about your stay!

Meredith’s cottage in Jamesport is the perfect North Fork getaway—spacious yet quaint, with incredible charm. The beach views are spectacular, offering peaceful sunrises and relaxing evenings. Meredith was a fantastic host—super attentive, thoughtful, and made us feel right at home. The location couldn’t be better: quiet and serene, yet close to everything from wineries and farm stands to local restaurants. It’s a quintessential North Fork home, and we can’t wait to return.

This was our second time staying at Jackie’s home and we can’t wait to return again soon! The space is perfectly located just a short walk from downtown Greenport. Everything you need for a relaxing weekend stay.

Completely great place! Looked like the photos but even better! Super responsive! Great stay

Such a cute little place and Tasha was very responsive. She took care of all our needs as soon as we reached out. Would highly recommend!

I enjoyed every minute of my quick escape to Montauk! Check in and out was simple and convenient. The room was clean, private, and peaceful. Plus location has a beautiful view and is within steps to the beach.

Spent to my birthday here with my husband, dogs and toddler. Had my gender reveal birthday cake, outback under the sunset. Truly magical.✨ The backyard was ideal. Was able to tie the dogs to the deck with a 20 foot leash. It kept them contained to the backyard & away from beach goers on foot and other dogs. The dunes kept the backyard private you’re not staring at your neighbors. Felt so secluded. I also have some mobility issues and you couldn’t ask for an easier way to enjoy the beach & get your toes in the sand. The house & deck are spacious and easy to navigate with a walker. Was able to add extra days to our stay. Would 100% stay here again.

We loved the location and the place was beautiful. Its was nice and clean. Definitely will be booking again

Fantastic location! We were literally a two minute walk from the beach. The studio apartment was as advertised and we would stay there again. We highly recommend!

An amazing stay overall. It was comfortable for 6 adults. Spencer was extremely helpful throughout our stay — I had lots of questions and Spencer was quickly responsive. The house itself is beautiful and has that eastern Long Island charm. The backyard had lots of space and is well maintained alongside the pool. We also enjoyed a sunset evening at the beach which is just a few steps away. It was a wonderful weekend and I am certainly looking forward to staying here in the future!

What a dream stay! From the get go Vanessa was responsive and helpful with the booking. Our Girls Gone MILD Bach trip needed a home that would keeps us in vs out and this GORGEOUS home with it’s beautiful garden and pool/jacuzzi/patio made it the most memorable stay. We loved playing board games in the living room and dining at that warm long table! The kitchen was fully equipped with everything we needed as well (plenty of wine glasses for all the Wolffer Rose we got) and don’t get me started on the book in the basement rooms. There were towels, beach gear, umbrellas, and all the things you could possibly need for an unexpected rainy day or to have a good time at the pool/beach! Also the walk to the public access to the private beach was a short walk through such lovely neighborhoods! I’m hoping to come back and stay here again! The girls and I loved waking up to the pristine garden views and the occasional bunny that would hop across the lawn! We were definitely sad to leave ˙◠˙

Dan is the most responsive host we've ever had. Usually we got a reply within minutes or even seconds. He happily got the hot tub heated up for us when we needed it and replenished our towels within an hour of our request. That hospitality made our stay so much better. The home is beautiful! It's right on the water, and features lots of luxurious tile, a huge patio, a little dock and lots of windows and open space from which to see it all. We especially loved the hot tub. I wouldn't hesitate to stay again if I'm ever on Long Island again.

Loved Samy’s corner unit, which gave us a bit more privacy and quiet than other parts of the property. The studio was as described, with great light and well-cleaned prior to our arrival. Enjoyed use of the tennis courts every day. Only minor disappointment was that we were not yet allowed to use the pool, which we were told would be ready by Memorial Day (we were there one week prior). Still, a worthwhile stay and I’d come back and recommend it to others.

Great spot for a few days in Montauk. Really close drive to town only about 15 walk into town. Great food cart on property open when the weather is good. Amazing ocean views from most rooms hard to find in the Hamptons.

Great and responsive host. Home was lovely and we felt welcome. Host responded quickly to questions and requests. The home was very peaceful and relaxing. We really enjoyed the outdoor patio and pool area. I would recommend for a peaceful time away from the city.

Great location between Hampton Bays and Southampton. Place appears exactly as shown in photos; perfect for 2 people looking to enjoy the beach along the south fork.

I would highly recommend Laura and her rental! We had a great time. Can’t wait to go back.

A beautiful, relaxing and peaceful setting and a quick and easy trip to town. Great views and house was perfect with tons of amenities and perfect to bring our dog. Host was fantastic and so responsive. An amazing stay!

The cottage is cozy and well-appointed, nestled in a bamboo grove with a view of the sea from the front porch. Just what we needed for a weekend away from the city. Ron was super responsive when we had questions about the heaters. Easy to find and close to town. Overall a great stay.

Our second time staying here. This is the best beach bungalow in the area, and we can't wait to come back again. Krae is a great host -- kind and responsive.

We would just Like to Thank Benjamin and Blake for letting us early and depart late. I would like to relay to future guests that their place was awesome it fit the bill perfectly we traveled with a 6 and 5 year old and the the beach toys and chairs provided HELPED . The washer and dryer also sometimes its a little difficult trying to keep kids clothes clean HAHA! The neu=ghborhood was safe and clean with easy access to highways , Again Thank You Very Much. Oh by the way the kids loved feeding the rabbit family in the backyard.

Mia’s place is excellent. Exactly what the listing describes and more — Mia is a great host and super attentive despite us being a last minute booking, she even helped us through a tough time late in the day when I thought my daughter’s stuffie had been picked up by the maid service. Above and beyond!

Wonderful stay in Montauk. Family of 5 adults. We thoroughly enjoyed the stay. It takes 15 mins to walk to the grocery, or only 10 mins the beach and-or a few minutes more only to walk to the town center. The house has a Big smart TV. The backyard is enclosed and safe for children. The yard has a beautiful pergola and outdoor shower (perfect for sandy feet) . The finishes in the house are high quality. There are nice vintage art pieces. The house has both AC and ceiling fans working perfectly. The kitchen had a few missing things that we have communicated to the owner so they probably will be added for the next guests