House holiday rentals in Shelter Island Heights

Joe's place was perfect for a girl's trip with two 1 year olds. The house was beautiful and had so much personality and warmth. The area was super private and quiet surrounded by nature. Joe was very informative about check in process and recommendations were plentiful.

I stayed at Ashton's place by myself on a visit to see my parents, who also live in Springs. It was everything I could have hoped for. So peaceful, and such a beautiful space. Amazing high ceilings and natural light. The yard is gorgeous, so I can only imagine how lovely it is when the weather is warm. Ashton himself is very responsive and accommodating. I was sad to leave!

Our family enjoyed a wonderful post- Christmas getaway at Jennifer’s beautiful home. The house is fabulous - well- located, pristine , beautifully decorated and well-stocked. It was relaxing and perfect. We did not have much need to reach out (everything was effortless) but when we did, Jennifer was very responsive and helpful. Highly recommend!

Dorina’s home was the calm, peaceful reprieve from the city we were looking for. Her home was so comfortable and she went above and beyond to make sure we had everything we needed. The backyard was a little oasis with a large pool (with floats!), several (6 I think) lounger chairs, two 6 top tables in different areas and a functioning grill. We spent most of our time here! Dorina was fast to respond, helpful with recommendations and overall what you hope to have in a host. We would definitely come back to Dorina’s home!

I had an amazing experience staying at this Airbnb! Luz, the main host, was absolutely wonderful—so kind, welcoming, and incredibly helpful throughout my stay. She went above and beyond to make sure I had everything I needed and even took the time to recommend some great local spots to visit. Her hospitality truly made this stay special. David was also fantastic so professional and accommodating. He made everything so easy, from check-in to answering any questions I had during my stay. It’s clear he takes pride in ensuring guests have a great experience. The space was spotless, beautifully decorated, and just as described in the listing. It felt so cozy and inviting, and the little details, like the complimentary snacks and toiletries, made all the difference. The location was also perfect. I couldn’t have asked for a better stay. Luz and David are a fantastic team. I highly recommend this Airbnb to anyone looking for a comfortable, welcoming, and enjoyable experience.

House is well represented. Spacious, very clean, and great location. Good for families or groups of friends.

Five stars doesn't feel like enough, if anything I'd say everything was better than we'd expected based on the pictures and the reviews! First, as others have mentioned John was an incredible host, the place was well stocked and had all sorts of snacks and drinks (and a nice bottle of wine); he also bought us dinner and was very good about keeping in touch the whole time we were there. The house was amazing top to bottom, but I have to specifically call out the pool, which was jaw-droppingly beautiful and the perfect temperature despite cold weather outside. We loved the neighborhood and yard to walk our dogs, and the kitchen was great to cook in (made me miss having a gas stovetop). We'll definitely be visiting again, it was the kind of stay that sets a new bar for what to look for in a vacation!

Marks home was beautiful, peaceful and near to so many great areas. The pool and backyard were wonderful and relaxing. We loved it! Highly recommend!

Beautiful, clean property! Bedrooms were spacious and the beds were so comfortable. We enjoyed the hot tub while the snow fell...its a perfect weekend getaway house. I wish I could come back in the summer to enjoy the pool. AJ was very responsive and provided easy instructions for easy check-in.

The place was perfect! We had a wonderful girls weekend. Beds were super comfortable, place was spotless and beautifully decorated and quaint! Super easy walk to town and Jillian was a great host with prompt response. We will definitely book again! Thank you Jillian

Lovely, well kept and comfortably furnished. This home has everything you need for a comfortable stay. Owner is helpful and very responsive. Highly recommened!

Kate's place is an absolute gem! This was our first time to Shelter Island, and we loved the laid-back atmosphere. Kate's home has everything you need to have a relaxing weekend, from the amazing, heated pool to the kayaks on the beach, a 2-minute walk from the house! Having been in the hospitality business for over 25 years I tend to be super critical about cleanliness and amenities offered.....this house does not disappoint! We were a group of 10 attending a winery dinner and decided to stay for the weekend. We only left the house to attend the dinner, the rest of the time we stayed at the house, either in the pool, on the deck BBQing or inside chatting where there are two living rooms and a very well-equipped kitchen. The bedrooms were nicely decorated and comfortable! We would definitely recommend and hope to stay again. :)

We had such a wonderful stay here over New Years. Like many other reviews have stated, pictures do not do this home justice. It’s so much larger and more spread out than we expected. Perfect layout for two couples where we each felt like we had our own place, with plenty of cozy spaces to hang out too. The kitchen is SO well equipped for anything and everything. Beds and sofas were super comfortable and the we loved all of the charming touches of this historical home. The location is fantastic too. Walking distance to everything you could need and a quick drive to so many beautiful areas. I can imagine spending hours in the backyard when the weather is warmer too!

Our group has stayed at Patti's place twice a year for a number of years now. She has always been gracious & helpful, with a nice note and home baked cookies greeting our arrival! The location is quiet and peaceful, right on the beach, which is conducive to our desire for rest and reflection.

A lovely cottage on a quiet street (at least in the fall!). The interior is just beautiful with all the wood floors, walls, ceilings. The kitchen was - unusual! Clearly they had to retrofit an old home to accommodate modern appliances, but all worked well.

Kait was super helpful! She texted me a few days prior mentioning we could check in early! I have never had that happen before! The house was stunning, comfortable beds, well maintained and great location. We forgot a jewelry bag at the house and she sent a photo and arranged for our family members near by to pick it up. Highly recommend!!!

We had a wonderful stay. Cute and comfortable house in an amazing location. Very comfortable for a family of 4.

Erika's East Hampton home was absolutely perfect. She kindly accommodated our same-day reservation for our last-minute anniversary weekend getaway. It was much more space than we needed but honestly, it was reasonably priced for the off-season and had everything we were looking for: a peaceful location, close to amenities, beautiful decor, and a hot tub. The weather was lovely this weekend so we were even able to use the beach pass to sit on the beach and play board games. The space itself was beautiful and cozy, we really felt at home. We're already planning to come back next summer!

Location was perfect for us- easy to find and close to things that are important to us (family in area, beach, shopping). Fenced yard made bringing our little dog that much easier- especially during the rainy day! Kitchen was well stocked thankfully as we were cooking Thanksgiving dinner (but not well stocked in the casserole dish, baking tin department-- which is usually not an issue for most people!). Decent coffee was supplied with a Keurig. Beds were comfortable. Everything was clean. I liked that he didn't leave a long list of what we needed to do before leaving as that is often a hardship when trying to leave a house with kids before a long drive. I would definitely stay here again.

Great stay! House was exactly as described / in photos. Hosts were extremely responsive and easy to communicate with.

We had an amazing stay at Alissa and Danny’s house! The location is perfect—convenient to everything we needed, yet peaceful and relaxing. The house is carefully designed with families in mind, especially with kids. It has everything you could possibly need for young children, from toys to safety features, making it so easy to enjoy our time there. We were so impressed that we’ve already booked again for our next trip! Highly recommend for any family looking for a comfortable, family-friendly! Mine Gur

The house and area were ideal. I had moved from the area the year before I rented Melissa’s home . My partner and I lived just a mile and 1/2 from the rental. He passed away and this was my first time back on the North Fork. Having lived in the area over 30 years it was great to be back. Melissa’s home was perfect close to all my friends and my partner’s family. The house was ideal with 3 levels it was perfectly suited for me and my two dogs to have our space and my two housemates had their own space. I look forward to possibly renting her home next year as well.

Host is very friendly and polite. she responds to your calls and texts whenever we do, my kid 1 year she has so many things to play in the house and well spent

We must have passed the residence hundreds of times going out Montauk over the past 40 years. What a hidden gem. We were so fortunate to have the opportunity to stay at this location. The home was very well appointed, tidy and clean. What a gem of a home, even in the off season. We would love to return.