Vacation rentals with a kayak in Shelter Island Heights

Charming home very well maintained and super clean! This was the perfect location to experience all the local charm of Port Jeff! The house had everything we needed - my family felt right at home the second we walked through the doors. Jennifer was proactive with clear instructions - we would 1000% stay again.

We had a wonderful stay at Harbor House. The view of Napeague Harbor is gorgeous and the sunsets are just next level spectacular. The kitchen is well equipped for cooking in and the furnishings are very comfortable. The location is great halfway between Amagansett and Montaik. We have rented so many homes over the years, but Rod’s house is by far in the most gorgeous setting. We cannot wait to return.

Bill’s place provided a wonderful location for our family of seven to spend our Thanksgiving holiday. The house was clean, uncluttered, and comfortable in every way. The kitchen had everything we could hope to find for meal preparation. The two sitting rooms provided delightful spots for reading, conversation or catching up on the television news. The upstairs bathroom was especially room and well-appointed. While it was winter when we visited, we could tell that this house would be a truly marvelous spot during the summer months as it had a great back deck and was truly only a hundred yards or so from a beach on the Long Island Sound. While it may not be the first choice of those who are on a tight budget, we recommend this home highly.

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!

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.

Laurie s place is very nice, spacious and clean. Plenty of space to eat, hang out and 2 bath. The fenced in yard is great for dogs or kids. We weren't in full summer season so we're not taking advantage of the beach and water options but they offer alot. Allowed for an early check in which was great as we were in town for a memorial service.

Right off of 27 so it is super easy to get to. House is on a nice private street with beach access. We walked to the beach several times a day to let the kids play and the dogs run wild. It was beautiful. House is exactly as described and Roger and Amy were great at responding. Quiet neighborhood. Only about 5 minutes outside of Southampton town.

Meaghan’s place was everything we needed and more! Loved the views, the waves, the sea breeze, the bird observing, the walks to Grass Island, the together time with family in a quiet, secure & well appointed setting. Meaghan equipped us with everything! She was very responsive to answer questions. This is one of those treasured memories. Can’t wait until we get back again to this special location! Thank you!

Had a great weekend at the cottage! Meredith was so great letting us check in early and was super helpful and responsive. The cottage is gorgeous and has everything you need. Loved it! Thank you!

Our stay was perfect! The home was so clean and Denise even left us a baby gate for our 1 year old. Denise was very responsive and provided great recommendations of places to eat and things to do. There is a private beach across the street but we walked about .25 miles down the street to the Silver Sands State Park beach so that our 1 year old could play in more shallow water before high tide. We would highly recommend and will be back!

I thoroughly enjoyed my stay at this peaceful cottage. I enjoyed sipping my coffee looking at the view of the cove from the deck and the bird watching from the screen porch was a delight. The bed was comfortable and Gail stocked the kitchen with drinks and snacks! Gail's house is next door but the layout of the deck and screen porch offers great privacy. A perfect place to get away from it all and relax in nature.

Returning guest, we had a wonderful weekend at Michelle's idyllic home. Plenty of space for our two families and 3 kids. The kids love having their own space in the "she shed" while the adults enjoy the lakeside views from both the yard and inside the spacious living area. The house is always immaculately clean. Beds and other furnishings are comfortable, and the house is an easy drive to everything the North Fork has to offer. We look forward to returning (again!) soon.

My stay at Chris and Ann’s listing was the perfect last stop on my stay in CT……beautiful, welcoming accommodations enhanced by the natural, peaceful, setting of the salt marsh and wildlife. It’s absolutely a favorite place the next time I’m visiting CT.

We had an amazing stay with Sean and Jenny. The property is perfect for a peaceful getaway from the stresses of daily life- unique location, impeccable views, spotless and well furnished house, we were able to unplug and enjoy some nice quality time. Sean is a gracious host, offered lots of local recommendations as well as details of the house that were very helpful. Was responsive for questions and easy to communicate with. Hope to be back one day!

We had a wonderful stay at Daniel’s home in Cutchogue. It was our second stay at one of his properties, and it did not disappoint. The house is just as described, clean and well stocked, and makes for a wonderful landing spot when exploring the North Fork.

This is a lovely house in a lovely location. We enjoyed walking just steps to the little beach. We also liked how it felt removed from the hustle and bustle yet we easily drove into New Haven and surround towns everyday.