Family-friendly vacation rentals in Southold

This is the 2nd Thanksgiving weekend we spent at Deeanna's. Her home is beautiful, comfortable and each detail is thought though in the best way. Deeanna went above and beyond to accommodate my family and we are so grateful to her. The kitchen is perfection and the bedrooms are lovely and comfortable. The scenery and views are breathtaking. Overall, this home is a total gem. Thank you, Deeanna! We hope to come back next year!

Myself and a few friends stayed here to celebrate a 40th birthday and we all loved it! The space is so unique yet still cozy and very relaxing. We were able to cook easily in the fully stocked kitchen all of the bedrooms were comfortable. Spent a majority of our time just hanging in the living room, but did get around to utilizing the hot tub. Would highly recommend this place for a nice relaxing weekend away.

Fantastic stay/fantastic hosts! My adult children and I spent a great weekend hosted by David and Abby. Their place was perfect for us and very comfortable. David reached out and described check in and proactively answered any questions we would have had. We were there in cold weather but I will earmark it for a warm weather stay as it has so many appealing summer amenities! We will stay again for sure.

A wonderfully relaxing, beautiful home to spend time with friends & family. The local restaurants in town are great and we also loved the Blue Point Brewery nearby in Patchogue. From the initial booking and until the end of our stay, David & Claire were great hosts i.e. very informative and responsive related to questions about our stay. We had a bedroom light issue and David was extremely responsive, and had his handyman come to the house to solve it, who couldn’t have been nicer! Would definitely recommend!

We had a fabulous time! Can't wait to come back. Was equally perfect for two toddlers as it was for four adults! Beautiful property, amazing hot tub, comfortable beds, great kitchen... everything was lovely.

Cozy and pretty home, all ready for a chill weekend. Cindy is super nice and easy to work with. Very generous too. The 2 pups loved the fenced in yards. Kitchen/dining room space is big and bright and awesome to hang out or read in the corner nook. I am sure the backyard and pool would be great in summer. Beds were comfortable. Thank you Cindy!

We had a wonderful stay at Jennifer’s place. It was.l beautiful, immaculate, and incredibly well equipped—especially for kids with the plethora of games and toys. Jennifer was responsive and a great host. The house is on a serene, dead-end street, and outdoor area is perfect for kids.

This house served our family very well for a multi-month stay. The house and property are just like the photos and all the amenities were great to have. Would recommend staying here if you are looking for a quiet place near the water in East Hampton. Petra was always very responsive with anything we needed and was an excellent host.

This is a lovely little beach cottage! We were very comfortable and had a great time! It was wonderful to have our dog with us! The location is beautiful and private, with access to a very special stretch of beach.

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.

Ed was great at communicating, house was everything we could have asked for. Would definitely book again!

This home is beautiful and so spacious! Proximity to East Hampton and Springs, yet very private and peaceful. Couldn’t recommend enough!

We had a wonderful stay at George’s. The unit is exactly as described, don’t be deterred by the adherence to the house, it’s completely private. It’s at a great location for north fork explorations and the amount of towels was outstanding!

This was a great find! I booked this Airbnb for myself and 4 other girls and there was plenty of room and space for us to hangout, sleep, and get ready. Walkable to town. Extremely clean and had all the amenities you would need for a short weekend getaway. Marianne and Steven were very responsive whenever I had a question. I would totally book this Airbnb again!

The house is beautiful! Great location. Amy and Roger were extremely helpful and responsive. Lots to do! We had an amazing visit!

Such a charming and cozy house, the photos don’t do it justice! Clean, well appointed, and comfortable. We had everything we needed and felt right at home. From the house we were able to walk to the beach (about 30-40 minutes along a safe route with sidewalks). The town is a quick 5 minute drive. We enjoyed the pool and the beautiful lawn. Ed made the whole experience seamless by being super responsive and helpful whenever we had a question.

We had a wonderful stay. Cute and comfortable house in an amazing location. Very comfortable for a family of 4.

The home was beautiful, just as pictured with natural light. The layout is great for families. There was plenty of space for entertaining and cooking. The home was fulled stocked with everything you could possibly need.

The house is beautiful, looks like photos. Stephen is a great host! Overall great stay, could not recommend more!

Mike is a great host with helpful recommendations and plenty of advice. The house is amazing. Well located, calm, clean and so convenient. The pool is huge and very deep. Everything is perfect. Felt like at home. We will be back

When you think "Hamptons" that's exactly what you get with this property. Cedar shakes, white trim, and a beautiful backyard. Because of the landscaping, the property is very private. There are also several walkable restaurants near the house. The train is also right down the street for guests looking to arrive from NYC or looking to head further out to Montauk. I would stay here again.

Our family enjoyed a wonderful post- Christmas getaway at Jennifer’s beautiful home. The house is fabulous - well- located, pristine , beautifully decorated and well-stocked. It was relaxing and perfect. We did not have much need to reach out (everything was effortless) but when we did, Jennifer was very responsive and helpful. Highly recommend!

We loved our stay here. The house was sparkling clean and the yard was big and beautiful. Can only imagine the vibes here during the summertime when the pool is open!

We absolutely loved staying at Christine’s beautiful home! The place was immaculate, and we particularly enjoyed the pool and fire pit. The location was perfect—situated in a quiet neighborhood, close to great restaurants, and within walking distance of the water. Christine was an amazing host, letting us check in early and check out late. She also texted to make sure we had everything we needed and were enjoying our stay. She even stopped by to share some great recommendations and ensure we knew how to use the house and pool code. We had a fantastic experience and would highly recommend this Airbnb to anyone looking for a relaxing and enjoyable stay!