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!

Cannot say enough great things about this house. I’ve stayed in many AirBnBs and other home rentals over the years and this was one of my absolute favorites. The house is beautifully updated and was extremely clean. The kitchen and bathrooms are gorgeous and have everything you need. Beds were so comfortable and the room darkening shades are a rare find in a vacation rental. Close to Greenport town and lots of wineries. Backyard was beautifully landscaped and was amazing for our dogs to run around. We will definitely stay here again!

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!

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.

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!

Giuseppe was a fantastic host! Communication was super timely and responsive. The place was exactly as described. Would definitely stay here again and highly recommend to others as well!

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!

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.

We had a lively stay at David and Michiko's place. It was a perfect little getaway for 2 young familes of four. The pool was great, and it was a short drive to the beach. Lots of great restaurants around also!

Harris was an amazing host! Very responsive and thoughtful. He even left us a basket weaving kit for the offchance that it rained during our stay. The home was stunning — beautiful furniture, stocked kitchen, and stunning art. Convenient to Southampton, East Hampton, and of course, Sag Harbor! Will definitely be staying again!

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!

Jessica’s home was absolutely beautiful! We had an amazing, relaxing weekend and felt right at home :) Jessica is an amazing host - absolutely recommend staying here!!!!

This house was PERFECT for us - four women returning to their college for their 45th reunion. The beds were comfortable and the neighborhood was quiet. The house was extremely comfortable. Carlos was responsive and helpful. We would definitely return to this house.

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.

Clean, spacious, and convenient walk to town and beach.

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!

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.

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.

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!