Kid-friendly holiday rentals in Shelter Island Heights

Beautiful house, perfect for a getaway to the north fork. Very close to a beach. Very clean and comfortable. Elizabeth is a great host. Highly recommend.

We went to Charles' home for a girls' weekend, and it was great! His home is beautiful and comfortable, and it's conveniently close to all that Greenport has to offer. We walked to restaurants and stores, and took an easy drive to multiple wineries. Would definitely stay there again when visiting Long Island.

This was our second time renting Brian's place for a getaway and this stay was as excellent as the last. We love this house so much and Brian could not be a better host. His communication is stupendous; he was always immediately available to respond to any questions we had.

We had a wonderful stay in Greenport! The house was comfortable and very well kept. Everything was pristine. The location was great- a few short blocks into town for shops and restaurants. We had an issue with the fire detector sounding and Kim was kind enough to compensate us for the issue. She is a great and responsive host. Would definitely stay here for our next visit!

This is one of the most soulful places to stay on Long Island, Greenport, our second visit. A true family gem with laidback vibes and stylish features.

Absolutely wonderful home. Stayed there as two families. Felt like staying at a friends house. Jake and Kim are flexible about check out which was greatly appreciated. Would highly recommend.

This spot was a great find. Hadn't been to Shelter Island before. I found the location super convenient. Literally every place I went was 5 mins on GPS from her house. She was very clear about everything, responsive to emails, and everything was as described, however the pictures don't do it justice. Beautiful home and pool, people came to clean the pool early one morning during the stay and were not disruptive at all. There were beach chairs, umbrellas, pool floaties, games, netflix, literally everything you could want or need. Loved our stay!

Great location, private and comfortable. Close to wineries and breweries. Very clean and convenient. I highly recommend.

We had a great weekend at Nicholas’s place. It was very peaceful in the woods, and we enjoyed using the record player and looking through the books spread throughout the studio. Nicholas was very responsive when I texted with questions and we used his provided recommendations to find breakfast and dinner. We’d definitely stay here again!

Incredible location! Walking distance to the town. The neighborhood is very quiet and we felt very comfortable all weekend long. Carole and Rich are wondering hosts, and the apartment had everything we needed. We would recommend!!

I can’t say enough good things about our stay at Holly’s place! We were traveling with 2 adults, an 18 year old and significant other and 2 teenagers and the amount of space was perfect! Everyone had room to spread out. The apartment had all the things you love about old homes, but all the updates that make life easier. The homemade banana bread that Holly left for us was such a personal touch and it was delicious. Erica greeted us with a warm welcome even though we arrived well past midnight. My daughter enjoyed reading in the cozy sitting area by the window. It was fun to watch the Hallmark movie that was filmed there. We fast forwarded the cheesy parts and enjoyed seeing the house in the movie. The area is peaceful and quaint. There’s a Dunkin about 5 minutes away, too which made our early mornings a little easier. Highly recommend if you’re traveling with a family!

We had a great stay. The apartment is even nicer than the photos can show, especially the high ceilings, and it's an easy walk to anywhere in Greenport. Amanda has provided every amenity you could need, including a full laundry. There's a very nice coffee maker, so don't forget to either bring coffee or K-pods (it takes either). Amanda was very responsive to any questions we had. If you're a breakfast person, Crazy Beans was a great classic diner spot, and we had a great Mexican lunch at Lucharito's.

Paris is a wonderful host. His property and cottage is a perfect retreat for two. Charming accommodations with a beautiful view and an easy walk to town. We’ll be back soon! Angelo C.

It was such a pleasure spending a weekend in Claire’s studio. The studio is very clean and comfortable, and my wife and I particularly appreciated the kitchenette, which allowed us to prepare a dinner one night and make our own pour-over coffee in the morning. We also loved hearing the birds as we woke up in the morning. And the location is terrific—an easy walk to the Southhold town center and a quick drive to other surrounding attractions like Greenport, nearby beaches, and wineries. Highly recommend!

It was a great stay, my second time staying here and Roisin is quick over communication and answering all the questions we had. Overall, great location and easy to get to!

We loved our time in Branford. We were so happy about how close to 95 it is. We will definitely stop here again on our next trip to Maine.

Great spot and at a really good price. Was visiting for a Yale event and was near enough to feel close without being too close to downtown. The area around the place is also super cute and not one I had explored previously. Huge plus for some good coffee shops nearby and of course Pepe’s. Camila was a great and responsive host. 10/10 would recommend Camila and this spot.

Harper House was absolutely beautiful! It is in the perfect spot in mystic to walk to pretty much everything! We walked to dinner and lunch everyday as well as the shops. Food is great in this area and the hosts left us some great recommendations. Highly recommend to anyone looking to stay in mystic!

We loved Montauk - low key, wild and upmarket at the same time. This apartment was perfect, super quiet yet near everything and loved seeing wild deer from the terrace

Lisa and I enjoyed our stay at Laurens place. Felt right at home. Very clean, open space. We had the best time and did not want to leave. We will be back for sure.

We had a great time at Adam’s place! The apartment was cozy, clean, and comfortable — perfect for a relaxing getaway. It’s just a quick 5-minute drive to Sag Harbor, which made it super convenient.

Super nice place good communication. All around worth it!

Just had a wonderful stay at Robert’s place! The place was impeccably clean, and Robert was incredibly responsive and friendly throughout our visit. While the manor has a charmingly vintage vibe and could use a bit of modernization, we truly enjoyed our time there. The warmth of the atmosphere made it feel like a home away from home. We recommend for anyone looking for a cozy getaway!

Highly recommend, I stay here regularly for work in the area.