Holiday rentals with a kayak in Shelter Island

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!

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!

Diana’s place was wonderful! She was incredibly accommodating, responsive, and helpful throughout our stay. Her property manager, Nick, was also great and made everything smooth and easy. We really enjoyed the variety of amenities—especially the board games, pool, and outdoor shower. Highly recommend this stay!

we had a quiet girls getaway to celebrate my sister getting married-upon arrival we checked out the entirety of the home…to which we were pleasantly surprised every corner we turned! exquisite home with comfortable, aesthetically pleasing furnishing and so much gorgeous natural light. the outdoor shower was a huge BONUS! heated pool had us outside moving our bodies more than we’d imagined and was such a fun way to spend time together. the living room is so cozy and a great space to have a game-night-in! i could go on and on about each detail but you should simply stay here and enjoy for yourself all this property has to offer!

Frank went out of his way to resolve an unpredictable issue caused by harsh weather, including driving hours in the middle of the night to assist. The house is beautiful and the place very peaceful.

This place is a gem! When we arrived the home was spotless and exactly as pictured. It seemed brand new and in excellent condition. The hosts were very kind and helpful and even gave us a bottle of wine and left bottled water in the fridge. The beds were so comfortable and the home was stocked with everything we needed. Our young kids loved swimming in the beautiful pool and we enjoyed exploring the rest of the picturesque property—so cool to see the wild turkeys walking around. We had a wonderful vacation and hope to return one day!

🌟 A Perfect Hamptons Getaway – Highly Recommend! 🌟 We had the pleasure of staying at this beautiful Airbnb in the Hamptons for two days, and it was everything we hoped for and more. The home is a stunning blend of modern elegance and cozy charm. The interiors are tastefully decorated, creating a warm and inviting atmosphere. We especially loved the spacious living areas and the well-equipped kitchen, which made meal preparations a joy. Our host was exceptional responsive, accommodating, and genuinely kind. This Airbnb exceeded our expectations in every way.

Absolutely stunning! This house has an amazing view from gigantic glass doors in the main room. Details in the house are well thought out and of great quality, including a high end coffee maker and other appliances. The place has lots of premium touches that make this experience a cut above the rest. Steven is an amazing, friendly, and communicative host. Incredible experience all around, I would definitely book here again.

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.

Had a nice stay here with a group of people attending a wedding a short drive away.

This beautiful piece of heaven was better than we could have imagined. As beautiful as the pic are, they don't do justice to the serenity of this property. Our group already decided to come back again. Michelle was lovely and thoughtful. The house was stocked with all the essentials and more. The coziness was unbeatable. We had the best weekend with the best friends.

Wonderful bay side cottage! Stayed here for a long weekend with my husband and in laws. It’s a great location!! Water views, walkable cute neighborhood, and 20 mins from some of the bigger towns (Jamesport & Greenport) Place was clean and a fully stocked kitchen made it easy to stay in and grill out.

The house’s location was amazing and exactly as described. It was great having the beach in the backyard and being able to swim whenever I felt like it. There were plenty of areas to sleep, eat and sit either as a group or individually. The house was well stocked with anything you could need. I had an issue and Joseph responded and took care of it super quickly. There’s a lot to do in the area, but I didn’t get to a lot of it because I was enjoying the property so much.

Adriana‘s cottage is super adorable, clean, organized, very pretty. My family of 4 adults, one baby and 2 dogs were very comfortable here. We were here for a wedding weekend in the Hamptons so this was perfect for us. Quaint beach cottages neighborhood. Driveway had room for our two cars. We walked into an adorable tiny house that had everything we needed. Immaculate, spotless kitchen with all the necessary gadgets, Keurig, Brita pitcher, toaster, microwave, pots and pans, oven and stove. New towels and sponges. Snacks on counter, water bottles in fridge. Comfortable couch. Beds & comforters, clean and comfy. Plenty of pillows. Bathroom spotless, fully stocked. Back door leads to enclosed yard, great for the dogs. Front door leads to private sitting area, plenty of chairs. Front doors are new with instructions on the side as to how to lock them. We felt safe and secure. Lots of windows with new shades, for plenty of light. Thank you, Adriana, this was a perfect getaway from the city.

beautiful house, great location and very nice and peaceful neighborhood close to the beach and the vineyards the house is very well equipped ! Richard was very nice and even find a little bed for our baby boy ! thanks !

We enjoyed our stay. Erica was extremely responsive and stayed in touch throughout our stay. We were grateful for the heaters as it got a little chilly overnight. The house is immaculate which we really appreciated. Walking distance to the cute Main Street and even closer to a couple of coffee shops.