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!

We had the best thanksgiving trip here! It was beautiful and the space worked so well. We all loved it and would definitely recommend and come back another time! The view of the beach is incredible and lovely walks close by, the little town is cute and it was exactly what we wanted and not too far from the city, but we really felt like we were far away from any of the city busyness it was lovely!

Beautiful home full of personal touches and thoughtful accommodations. Brian was a communicative and friendly host, we’d love to come back in the summertime!

My best friends and I had a wonderful time here for my birthday and kept saying we felt like the real life “Little Women” sisters in such a charming cottage! Everything from the kitchen to the bedding was absolutely perfect and intentional. Our favorite part was the little whale butter keeper in the kitchen :). This was a great stay!

Cindy’s cottage was perfect for a long weekend - we (and our pups) loved staying here! It was incredibly cozy and comfortable, with fully fenced outdoor space for our dogs. The kitchen was massive and a great space to cook and hang out. The bedrooms were charming with very comfortable beds. Cindy was super responsive, friendly, and incredibly flexible for our check-in and departure. We really enjoyed our stay and would most definitely come back again!

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 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!

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.

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!

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.

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!

My family and I had a lovely week at Thomas’ home in Amagansett! Thomas was wonderful to work with - he is responsive and very helpful throughout our stay. The home is as advertised and is very kid/family friendly with a Pack n’ play, high chair and other kid toys. The outdoor space is WONDERFUL and very well maintained. The location is also great - walking distance to the Amagansett square and a short drive away from East Hampton! Thanks for a wonderful trip

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!