Pet-friendly vacation rentals in Southold

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

We had five adults, an 8 year old, a baby and a dog converging for some time together on the east coast, and Hattie’s house was perfect for us. Lots of room for all, lots of great spots nearby, and for the few small issues that arose, Hattie was very responsive. But honestly, it could have been a lot worse and I’d still have given it five stars for the bocce court alone.

We had a positive experience staying here. Laura was very informative and responsive throughout the whole process. The property was nice and located conveniently for activities planned during our trip, and had all the amenities that we needed. Would highly recommend!

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 a great stay for a girls weekend! Super central location, walking distance to several wineries and restaurants, and host was extremely easy to communicate with.

We had a wonderful stay with my family! Everything went smoothly from start to finish. The check-in process was easy and communication was clear and prompt. Anisha and Rob are great host, very friendly and responsive. The space was exactly as described—clean, comfortable, and well-equipped with everything I needed for a relaxing stay. The house is spacious. I really appreciated how well the place was maintained. I would definitely stay here again and highly recommend it to anyone visiting Southampton!

Great place. Easy walk to downtown Greenport. Jackie is a very responsive host and gave great recommendations for wineries and restaurants

We really enjoyed our stay at the beach cottage. The location is great, you can see the water from the garden and the beach is right around the corner. The place looks exactly like in the pictures and you find everything you need inside, kitchen, cleaning, beach equipment. Gabriel was helpful and always responded quickly. We enjoyed dinner at Legends down the street multiple times. And for those who want to enjoy a glass of wine on the terrace or in the back patio, there is a great wine store next to Mattituck marketplace named Vintage Mattituck, best prices we have seen in the state of NY and very good selection as well. We enjoyed walking on the beach and visits like to Greenport, Sag Harbor, Southampton. We can definitely recommend staying here on your visit to Long Island!

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

Gorgeous house and property that is even better than the photos. Like other reviews have mentioned, the highway noise in the backyard is definitely present, but easy enough to ignore. Really enjoyed our stay and communication was great!

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

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.

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!

I can’t say enough wonderful things about this spot and Monika. This is our second stay- my husband, toddler, dog and I loved it last summer and came back. The back sliding doors open onto a porch where birds chirp and visit all day. The bright green lawn under towering trees is perfect for playtime or a family picnic. Little touches of thoughtfulness and charm are just everywhere. Monika’s hospitality is unparalleled- snacks and a handwritten note upon arrival, homemade treats throughout our stay, and nearly instant responses. Without being asked, she even sent us a hand-drawn walking route for a dog and baby and directions for getting there. Beaches, playgrounds, town centers, bagels etc are a short drive. The street is busy so wouldn’t go for a nearby walk necessarily but thats pretty standard throughout the Hamptons. For parents of young kids: FYI there isn’t laundry, but truthfully I just packed more- that’s how much we liked it. A laundromat is also nearby tho!

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!

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.

We very much enjoyed staying in Meredith’s place. The cottage is surrounded by trees so it feels secluded and peaceful. The cottage is elegantly decorated; there were so many nice books around which we enjoyed checking out. Meredith was so nice and responsive. We will definitely go back.

This Airbnb was the best one we have ever stayed at! The apartment was sparking clean, spacious, and perfect for a weekend getaway. Parking is easy as street parking is free. We were able to park on the side street next to the apartment. Beth is an AMAZING host; she was responsive and helpful! You cannot beat the location! The Airbnb is close to all of the vineyards, great restaurants, and shops. We hope on our annual North Fork trip that we get the chance to stay there again!

Absolutely gorgeous home - the decor, linens, and amenities were top notch. Beautiful, private large backyard where we spent much of our time. As a family of 6, we utilized all of the rooms and it was the perfect space to bond and hang out. Walkable to the beach, park and all of the great restaurants in town and just a short drive to so many awesome spots in Orient and the north fork. Would love to visit again!

Stayed at Danielle’s home with a few of my girlfriends for a chill weekend away from home. Lovely and cozy space and beautiful neighborhood where we were able to catch some sunsets at the beach down the road. Perfect size for me and my friends. Hoping to make this a yearly tradition :)

This was a lovely cottage and location, part of a private beach community, on a very quiet road, with partial views of the Long Island Sound. Gail was thoughtful to put out a nice welcome basket and some cold sodas and bottle water in the fridge. Perfect spot for two to three people. Close to Guilford main green, dock and nearby Stony Creek and Madison. We didn't make use of the bikes and kayaks bc it rained in the mornings, but we enjoyed one of the two beach just a few minute walk away. Jacob's cove area is a gem.

Had a wonderful stay with my family. Clean, comfortable, great location. Good communication. Had a little trouble with the front door first day but someone was available quickly to help. A+

This apartment is the most perfect space for a getaway. The photos dont do it justice, I was shocked at how big the space was. Right in the heart of the town I could not have asked for anything better. Lucharitos crew downstairs although not affiliated was nothing but friendly and considerate of our stay. I will be back for sure!