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!

I absolutely fell in love with this place and location. The beach is at your back door. Great restaurant within a few feet of the house. No need to leave the house. Everything is supplied for you. Super clean, beautifully decorated and the most beautiful, peaceful sunsets you could ever hope for. I can’t wait to rebook!!! Wish I could have stayed longer. The property manger was super nice and very accommodating. It was one of the best places I’ve stayed at!

Great location. There are several bars and shops within walking distance (beautiful walks around the area including to Dayton Bay). The house is spacious and clean. The backyard is the star. We loved the pool and hot tub. Abby and David are very friendly and responsive. It is located very close to town and about a twenty minute drive to Montauk.

As many other comments have noted, this place is truly exceptional and exceeded my expectations. It was one of the most adorable and quaint cottages I’ve ever seen, beautifully and whimsically decorated but still comfortable enough for my young kids to love and have a ball in. (They especially loved the Halloween decorations and the candy bar!). Thank you for a lovely stay!

Very comfortable and lovely home. Wonderful hosts very responsive.

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.

We spent a week at Joe‘s house and couldn’t be happier. The house, property, and surrounding area was amazing. Everything was super clean, and you won’t find a spot like this anywhere else. The master bathroom is incredible. Already trying to figure out how I can replicate that shower in my own house lol. would recommend this place 100%

We loved our stay at Chandra’s place, it was peaceful, super comfy and was close to everything we needed. It was great to enjoy a few runs locally and come back to the private garden and hot tub in the evening. The property was beautiful and well stocked with towels, soft bedding and kitchen equipment. I’d love to come back again in the future

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 both proactive and responsive in his communication. Flexible check in time was a plus as well. The house was as described and clean. Great place for a family stay…

The house was perfectly and beautifully appointed. Looks exactly like the pictures and had everything we needed. Easy walk to town. Would highly recommend!

I booked last-minute for a solo stay, hoping my wife and dog could join mid-week, but logistics didn’t quite work out, but even then was a win/win situation. Bryan was kind, intuitive, flexible, and at ease with my changing plans. And over the next few days, you could see more of how his skills as a contractor, photographer, musician, studio owner, and long-standing good citizen served him in shaping, maintaining, and hosting this place, and offering suggestions about his town and the area. I was carless, but he lent me a good bike, and, walking-wise, it's ten-minute to the Elizabeth Morton Wildlife Refuge. So the main apartment is cozy, private, with its own entrance, doesn't even feel like a part of the main house. Occasionally, I heard a happy dog greet him, or a trace of his gentle guitar, but it was wonderfully quiet overall, especially the yard. The extra cabin with a sauna was a great perk I’d love to enjoy more with family next time.

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!

Very nice setup for two couples, a baby, and a dog - could spread out with bedrooms and full bathrooms on each floor. Comfortable space with amenities you'd want while traveling with a dog and a baby (fenced in yard, laundry, etc). Very walkable to all the shops & restaurants in town, and easy drives to wineries & breweries. The only drawback was that it was close to a fire station and the sirens woke the baby from a nap.

Jennifer was a gracious host. We had everything we needed for a perfect stay. Highly recommend! Thank you for hosting us! Joe and crew

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

Michael's home was absolutely amazing ! Beautiful, clean , comfortable. You literally feel at home but better ! I absolutely recommend this airbnb . Definitely looking into renting again for the summer to enjoy the pool . Michael is an amazing host , super friendly and very very accommodating. We had a wonderful weekend!

Loved the place! Clean and comfortable. Had everything we needed. Perfect location near family for the Thanksgiving holiday. The main street w/ restaurants & shops was just 10 min away. Robert and Chris were very responsive and provided detailed instructions and many recs for the village. Very kind! 10/10

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

Perfect house for our Thanksgiving gathering. Felt like home. Thank you.

This stay renewed our love of opting for a rental instead of a hotel. Cindy was an amazing host with plenty of wonderful local recommendations, very accommodating check-in and check-out processes, and easy instructions for everything. The house was beautiful and provided quick access to all the Hamptons hotspots and places of interest. We LOVED our stay and would 100% rent this house again. Thank you for making my birthday so special, Cindy!

Had a great week in Ben’s home. Beautiful property, comfortable, well equipped and plenty of space. Location is perfect, an easy walk to shops and restaurants yet quiet and private. Highly recommend.