Family-friendly holiday rentals in Montauk

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.

sweet, comfortable cottage close to everything, but feels tucked away and private. lovely for off season with the fireplace and hot tub.

We headed to Cindy’s rental for a weekend getaway with our two-year old son, dog, and mother-in-law in mid-March. It was the perfect spot! Intimate, cozy, but plenty of space for us all to spread out. A great kitchen that was sensibly laid out and full of everything we needed. It was a terrific jumping off point for poking around the Hamptons (extremely convenient to East Hampton’s main drag), and so comfortable and lovely to return to. Cindy is a fantastic host. So attentive, kind, and helpful. She did a terrific job providing our family a great place to stay, and was so accommodating. We are grateful! We highly recommend this spot for a quick and easy small family getaway!

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.

Petra is an incredibly responsive host, always available and ready to answer questions. The house is quirky (and I’ll say not maybe the best if you have mobility issues), but very cute and perfectly set up for our needs. The yard is excellent for dogs, and the location is also great, with a bay beach in about a 20 minute walk and a coffee shop and a few restaurants as well. Thanks Petra!

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 home is top notch!! Esther is truly amazing and everything was excellent. The kitchen is amazing, the basement play area was awesome and the rooms were perfect! I will be staying here again!

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!

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

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!

We came back to stay for a second time and hope to be back for many more! The place is exactly as advertised, beautiful, and an easy walk into town. Marianne and Stephen were super flexible with a few requests we had around the stay and so easy to communicate with. Greenport is the best and this home is amazing - you won’t regret booking here!

This is our second time time staying at Ron’s airbnbs We absolutely love it there ! Ron is great! Super accommodating and easy to get a hold of. The rooms are always clean and it feels like a home away from home We will definitely be coming back!

Wonderful time staying at Milton and Megan's. The location was perfect and the home had everything we needed and more to work remotely for the week. Thank you!

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.

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 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!

We had a great time. The house was really big and perfect for a big group. The common areas allowed us to spend time together and there was so much to do in the house and in its surroundings. We definitely recommend it.

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.