Pet-friendly holiday rentals in Shelter Island

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.

Maher’s home is so elegant and mid —such great taste. He was such a kind host and so very easy to communicate with. The pool was lovely and the garden and back so pretty. We had a brilliant time! Thank you.

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.

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.

Perfect beach down the street! We loved how close it was to everything including most Hampton towns. Absolutely wonderful home for the two of us and our two small dogs, especially the large fenced in yard for them to run. Every amenity is included and we loved the modern look of the home. Also loved the small, quiet street close to Mattituck's main street with charming restaurants. Make sure you check out the Magic Fountain for ice cream and Love Lane Kitchen!

Ashley’s house is the perfect get away. I booked this house for my family to stay for my wedding weekend. My mom had never stayed in an Airbnb before and I’ve never seen her so happy and relaxed. She truly enjoyed her first Airbnb experience at Ashley’s place. It was exactly as described and the view is beautiful. Ashley was very responsive and made sure to answer any questions I had.

An ideal location in Southampton, Lori’s house is clean, cozy and peaceful; we thoroughly enjoyed spending our New Years there!

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.

Sarah is an amazing host - super quick responses to questions, friendly, helpful, it was such a pleasure to stay at her house! The house is more than that - Sarah makes it feel like home! From the countless comfy reading nooks that our teenagers loved and used, to the awesome outdoor space, the pool table & wine cooler and well stocked kitchen all the way to the nice touch of live plants (because let's be honest, at how many AirBnBs have you have live plants before?!). We felt right at home and are definitely planning on coming back! Highly recommend!!

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.

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.

This was our second time staying at Ron’s place, and it was so great! The location is wonderful, the place is super dog friendly, the beach is perfect location. It’s a cute group of cottages down old Montauk highway, so away from the hustle and bustle but close enough for Ubers and driving! Can’t wait to stay again!

Great location in the middle of the Hamptons - extremely close to Sag Harbor. Backyard is immaculate for a relaxing trip away from the city.

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!

“A Wonderful Stay!” I had such a pleasant experience at this Airbnb! The space was clean, cozy, and exactly as described. The host was incredibly welcoming and attentive, making sure I had everything I needed for a comfortable stay. The location was perfect—quiet and peaceful, yet close to everything I needed. I especially appreciated the thoughtful touches throughout the space, which made it feel like home. I wouldn’t hesitate to book again—highly recommend! Feel free to customize it with any specific details about your stay!

This is the second time we stayed at Kim’s. It was another pleasant experience. Kim is responsive and easy-going. Her home is welcoming and very dog-friendly. We love that Kim has beach access and it is walking distance. The convenience of her home being close to Southampton and Sag Harbor restaurants and shops is a plus. Thanks for having us, Kim. We will be back. xo - Dave, Sasha & Ginger.

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!

My friends and I booked Renee’s place for a relaxing getaway weekend. The house was exactly what we needed, clean, private, and full of everything we needed. Renee was responsive and flexible and overall just a wonderful host. We would stay here again in a heartbeat!

Wow, where do I even begin? The photos don’t begin to capture the true beauty of this bay front gem in Southampton’s North Sea community. From the inviting, open-concept design that feels both spacious and cozy, to the serene outdoor retreat surrounded by lush greenery, every corner of this property is a slice of paradise. The views of the bay and sunsets truly take your breath away, making each moment feel magical. Petra is the ultimate host—gracious, thoughtful, and always quick to respond with helpful communication. She ensured our family’s stay was nothing short of perfect. This is definitely a place we’ll be returning to, and we’ll be counting down the days until we can experience this peaceful haven again!

This is an absolute gem of a find. It’s close to numerous vineyards and a seaside port for deckside drinks and quaint shopping spots. The ferries to Southhampton is only ten minutes away and the ferry to New London is also only about 20 minutes away. The cottage is super cute and has everything you need. Perfect.

Great weekend on the North Shore of LI. My husband and I came for a wedding in the area and we were so happy we stayed at the cottage. The beach is so close we walked over and everything we needed was right there. We even enjoyed some wine and cheese on the outside porch before we walked to dinner at Legends. Would definitely recommend and hope we can get back to the cottage again.