Pet-friendly holiday rentals in Shelter Island Heights

We had a fabulous stay at this adorable cottage. It had everything we needed and more. Great spaces indoors and out to hang out, walkable to one of our favorite wineries, other wineries & restaurants close by. Appreciated having a tandem kayak to use & explore Goose Creek. Enjoyed watching birds, including Baltimore oriole parents in a nest in the backyard. Would return again. Thank you!

The house was very clean, well-decorated and cozy. The appliances were all updated and nice to use. We enjoyed staying in the area as it was half way between Sag Harbor and Southampton. Would stay again. Thanks for the hospitality!

Beautiful home, very clean, spacious and comfortable to stay with the family. We used the grill on multiple occasions and it was easy to use. The fire pitt was also enjoyable. The kitchen was well stocked, would bring own source of caffeine if you’re picky with your coffee though. Stephen, the host was very responsive and easy to reach when asked questions. The one thing I would recommend is to check in with the host if the pool is available to use prior to booking. Overall a great experience, would stay with them again.

I had a very nice stay at the Rex. It is dog friendly and very clean. Although my space was private, there are other rentals nearby and it had a camp like feel. I would stay there again if need be.

The house was clean, well-decorated, had all the things we needed, and private, with a long wooded lot leading down to the bay. We women friends were totally comfortable there. When we couldn’t find the entrance to the driveway off the main road, she stayed on the phone & directed us until we found it. Excellent choice!

I do not even know where to begin.We had a last minute change from our other booking and was completely stressed but Harris came in and saved the day with making it so easy for us to book his house last minute.From the minute we arrived to the personalized note with fresh flowers to having every product we needed in the bathrooms .The home was beautiful and very homey and enough space for all of our guests .The location was fantastic and we can’t wait to come back .Harris was the best host and my daughter had the best week .If you are looking for a fabulous house with a great location look no further .Harris ,we can’t thank you enough.We will definitely be back .

Dewey’s place is such a dream! Everything is freshly renovated and just feels so crisp, clean, and stylish. You can tell so much love went into the design it’s the perfect mix of modern and cozy. We felt right at home the second we walked in. The kitchen is gorgeous, the bathrooms are spa-like, and every little detail was just so well thought out. Dewey was the sweetest host super responsive and made everything totally seamless. The location is amazing too quiet and peaceful, but still close to all the fun spots (beach, town, restaurants). We didn’t want to leave! Already planning our next trip back. If you’re thinking about booking, do it you’ll love it just as much as we did!

We had a lovely stay at Roger and Amy’s place. The location was great - close to Southampton, a short drive from Sag Harbor etc. The home is charming and comfortable. The kids loved the heated pool and spent hours in it every day. Roger and Amy were also super responsive, with advice and help when we needed it including with a very sweet gift for our 3 year old whose birthday we were celebrating. All in - a phenomenal time!

Great host, great house with a bunch of fun things to do walking distance. Would definitely recommend and will 100% be booking again!

Marta could not have been more accommodating! She was responsive and provided everything we needed. She even went the extra mile and insta cart-ed garbage bags and paper towels when we ran out. She could not have been a kinder host! We had the best weekend and would HIGHLY recommend staying at Marta’s place! We will definitely be back!

Ashton’s house a very comfortable and extremely clean home. It is spacious, allowed tremendous privacy and met our needs perfectly for an amazing family vacation. Everything was just as explained with no surprises. Great stay and a very accommodating host.

Wendy’s house is immaculate, tastefully decorated, very spacious and extremely comfortable. Her instructions were clear and her responsiveness immediate. We would absolutely consider staying there again.

Our hosts were amazing. They responded quickly. They were very welcoming to us and provided easy-to-follow instructions. The location was great and the house was lovely. I would definitely stay here again.

Our family had the most amazing weekend at this home. Benjamin was very responsive and accommodating. There was not a detail missed in the home and outdoor environments. Even though it rained we had a full day of entertainment at the home. You will not be disappointed.

Nice private quiet location but close to beaches and main street shops and restaurants. Convenient to visit many local vineyards within 15 - 20 minutes. Home is comfortable and nice set up.

My girlfriend and I had an amazing time at Ron’s Cottage, it was beautiful and incredibly peaceful, very easy to get around steps from the beach. Listening to the waves crash on the beach from the kitchen was my favorite part. 10/10 wound stay again!

Had a great stay at Venetia’s. The house is located within easy walking distance to the water and downtown. The street is surprisingly busy but we still enjoyed the screened-in front porch. If you have a dog, the backyard is large and would be great. The kitchen is fully stocked and has everything you’d need. We enjoyed our stay and the easy check-out was much appreciated.

Quiet, peaceful. Pictures do not do this place justice. Perfect place for 2 couples or 2 couples and kids. Set up was great.

Dave was an amazing host. Incredibly responsive, everything was clearly communicated, and very helpful. The house was perfect for our family--great location near the beach with shops/restaurants nearby. Highly recommend!

Great stay! Although it was a rainy weekend, we had a great weekend!! There were close restaurants and coffee shops and the house itself was perfect. Great aesthetic to the home, very cozy and relaxing.

Thank you for the lovely accommodations! The space was well appointed and we loved the attention to detail with the decor and amenities. It was the perfect space for us with a living space, kitchen and nice bathroom. The airbnb had everything we needed and more! Thank you, Nina!

The cottage was just as described and the pictures were spot on. This is perfect for a get-a-way which is what we did. Had not been back to the area in over 20 years and wanted a convenient place to meet up with family and see the sights. It is just off the Main Road and 2 minutes to Route 48 for quick access to the vineyards, beaches, restaurants and more. If you like oysters, there is an stand right next door. If we decide to go back to Long Island, this will be the one I look for first.

Yvonne's place is wonderful, we spent six days there on a family vacation to celebrate a graduation and it was a perfect spot for a crowd. The description and pictures are spot on (maybe even better) and the place is very well maintained. The weather was not great - so we landed up staying in more than we anticipated and this was a great spot for that. The kitchen is well stocked, having a barbecue really helped, and the large windows and skylights kept us connected to the outside. Yvonne was also highly responsive in case we needed anything. Highly recommend.

I had a wonderful stay! The place was exactly as described—clean, cozy, and well-equipped. The host was friendly and responsive, making check-in and check-out super easy. The neighborhood was quiet and convenient, perfect for relaxing after a day out. I would definitely stay here again and highly recommend it to anyone visiting the area!