Kid-friendly holiday rentals in Southampton

We had an amazing stay at Michael’s Airbnb this past weekend! The space was exactly as described—clean, cozy, and well-equipped with everything we needed. Michael was a fantastic host: super responsive, thoughtful, and made us feel completely at home. The location was perfect for a relaxing getaway, and the setting was even more beautiful in person. Would absolutely stay here again—thank you for a wonderful experience, Michael!

Second time at this Airbnb and our whole group was very satisfied again. Very clean, great location, spacious house. All working amenities, clean linens, and plenty of towels, etc. Great location to get to Main Street!! Thank you David, we will be back.

What a dream stay! From the get go Vanessa was responsive and helpful with the booking. Our Girls Gone MILD Bach trip needed a home that would keeps us in vs out and this GORGEOUS home with it’s beautiful garden and pool/jacuzzi/patio made it the most memorable stay. We loved playing board games in the living room and dining at that warm long table! The kitchen was fully equipped with everything we needed as well (plenty of wine glasses for all the Wolffer Rose we got) and don’t get me started on the book in the basement rooms. There were towels, beach gear, umbrellas, and all the things you could possibly need for an unexpected rainy day or to have a good time at the pool/beach! Also the walk to the public access to the private beach was a short walk through such lovely neighborhoods! I’m hoping to come back and stay here again! The girls and I loved waking up to the pristine garden views and the occasional bunny that would hop across the lawn! We were definitely sad to leave ˙◠˙

Our group of 4 had a great stay at Riley’s! Location was super convenient, check in could not have been easier. We loved sitting on the deck outside and making an outdoor fire. Thanks for a great stay!

Benjamins place was a wonderful stay for our family. Coming from the City it was amazing to have so much grass with peace and quiet. It is a short walk to the Main Street and Sag Harbor downtown. We had planned to go out and enjoy some activities during the couple of days we stayed but instead found the place so relaxing we spent most of it in the home. The separate house was nice for a master bedroom and quiet. We would highly recommend this house to anyone wanting to have a relaxing and quiet vacation in the Hamptons near Sag Harbor. Hope to be back again!

We enjoyed our stay at Cosmo’s place. It was exactly as described, clean, and clutter-free. We were in The Hamptons for work, so it was great with Wi-Fi and the ability to cook. We also found the location very convenient and easy to find, and we would love to rent Cosmo’s place next time we find ourselves in The Hamptons!

The bungalow-style house in Hampton Bays was a lovely, quaint, and relaxing place for us NYC folk who needed a getaway that was fairly easy to get to. The place was very clean when we arrived, and was just as advertised in the pics. The grounds are lovely, and the deck is huge and great to chill out on. The Beds were all comfy for our tastes. The only minor complaint is that the gas was not turned on for the stove/oven use. There was a microwave, small toaster oven, and a gas grill on the deck, so we improvised cooking our meals. James was very much responsive with any and all questions. The street we stayed on is a quiet residential street. Very Hampton Bays! It was also nostalgic for me, since I used to go out there are a kid to my grandfather's bungalows. Definitely a spot we'd look forward to returning.

Really enjoyed our stay in Hampton Bays, Brian’s house is exactly as described. Spotlessly clean, very well equipped and perfectly located on the beach. We’d highly recommend the property to anyone, particularly families with young children. We ate next door at Rumba twice, Cowshed and Edgewater. All excellent and all walkable.

Cozy, well appointed apartment on a tranquil property in the woods. Short drive to the woods and to downtown Sag Harbor. All in all, a great pied-a-terre for our week in the Hamptons.

Had a wonderful trip and stay at Claudia’s! She was super fast at responding and had great local dinner recommendations and the place was great and very comfortable

Kelly and Rick’s place is absolutely beautiful and a perfect retreat for couples or anyone looking for a relaxing, scenic experience in Montauk. We’ve lived on LI our whole lives but never got to explore the east end until now, and Kelly’s place is the PERFECT location! It’s near town with great restaurants, coffee shops and grocery stores nearby, near hiking trails where we got to see seals and beautiful views of the ocean, near the lighthouse, near great fishing spots, etc., not to mention the gorgeous view of Lake Montauk right on their property. We used their fire pit and had a fire the last night of our stay as well! We had a BLAST and had such a relaxing weekend. The apartment was very clean and has everything you could need for your stay, and Kelly was super attentive and responsive when it came to answering our questions and inquiries. Thank you again for giving us such a beautiful place to stay! 10/10 recommend! We’ll definitely be back🌊❤️☀️

Stayed at this lovely home and I am so lucky to have found this idyllic spot. It is a well lived home that you get to stay in . The hosts are generous and kind. Both Paris and Clifton were helpful and responsive in their communication. Gave excellent recommendations. Paris welcomed us at the check in and it was so great to get a chance to talk for a little bit. I actually appreciated that a lot. The views are stunning and the space is really well done. It is what people wish for in their dreams. Thanks for such an excellent stay guys! Hope to be back soon.

It was a great stay, my second time staying here and Roisin is quick over communication and answering all the questions we had. Overall, great location and easy to get to!

We really enjoyed staying at Patrick’s place. It was private, quiet & close to our family. He had thoughtfully supplied many kitchen supplies, dishes & everything we needed for our stay. Very organized & had many spaces to keep our things . Very comfortable apartment & smelled clean & fresh. Even had a small vacuum we could use to clean up tracked in leaves & dirt. We were there for a week & enjoyed having a stress free place to unwind!

Great place ideally located next to town and the view is amazing. highly recommend in particular for short term stay.

patti was so kind and welcoming! check in and check out was smooth and made easy with how communicative patti and her co host lily were. the room was perfect for two people and incredibly clean. had everything we needed. Pattis recommendations for food and activities were great and although the weather wasnt amazing the bay beach being so close was so convenient for a nice walk :) Would definitely come back given the opportunity!

Great spot and at a really good price. Was visiting for a Yale event and was near enough to feel close without being too close to downtown. The area around the place is also super cute and not one I had explored previously. Huge plus for some good coffee shops nearby and of course Pepe’s. Camila was a great and responsive host. 10/10 would recommend Camila and this spot.

Harper House was absolutely beautiful! It is in the perfect spot in mystic to walk to pretty much everything! We walked to dinner and lunch everyday as well as the shops. Food is great in this area and the hosts left us some great recommendations. Highly recommend to anyone looking to stay in mystic!

We loved Montauk - low key, wild and upmarket at the same time. This apartment was perfect, super quiet yet near everything and loved seeing wild deer from the terrace

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+

We had a great time at Julie’s place. Would love to visit again…perhaps in the Fall. Loved the balcony overlooking the Sound. Julie was very responsive to my questions. She got back to me immediately. I would highly recommend Julie’s home!

We had a great time at Adam’s place! The apartment was cozy, clean, and comfortable — perfect for a relaxing getaway. It’s just a quick 5-minute drive to Sag Harbor, which made it super convenient.

We had a great stay! Instructions were clear and the home had everything we needed.

Just had a wonderful stay at Robert’s place! The place was impeccably clean, and Robert was incredibly responsive and friendly throughout our visit. While the manor has a charmingly vintage vibe and could use a bit of modernization, we truly enjoyed our time there. The warmth of the atmosphere made it feel like a home away from home. We recommend for anyone looking for a cozy getaway!