Family-friendly holiday rentals in Southampton

We loved staying at this home - it was the perfect place for our group of ten. The outdoor space was definitely the highlight, with the pool & spa being our favorite part of the trip. The only thing to note is that we weren’t supplied quite enough toilet paper or paper towels, though I did not reach out for more - It was the last evening when we ran out and we were leaving early the next morning. The trash requirements were a surprise after booking, but going to the transfer station was easy enough, and it is listed on the house rules. Overall, an excellent stay and would absolutely return!

We had an event nearby and Brian’s place was a great base for us. Lovely and peaceful neighborhood. Brian was super responsive and reached out to us when the house was ready(before the official check-in time). Would def recommend to anyone!

Andreas’s place was everything it described and then some. It was modern, nicely air conditioned and had 4 amazing bedrooms each with a private bathroom. The kitchen was functional and open to the dinning area. It had a lovely wrap around porch in front and patio in back with grill, hot tub and outside seating. As well as two lounge chairs. It was only a short drive into Sag Harbor yet it was in its own little neighborhood were we could walk 6 minutes to a private beach!

Amazing! We really enjoyed our stay. Abby and David are extremely hospitable, responsive, and friendly hosts. The house is beautiful, clean, and well-located. The pool, hot tub, desk, and back garden are even larger and more beautiful in real life. We will definitely be back. Thank you Abby and David!

This was one of the most thoughtful airbnb experiences I have ever had. The attention to detail was extraordinary. Cindy provided everything you could need -- a perfectly stocked kitchen, umbrellas, sunscreen, bug spray, first aid, yard games, pool floats etc. The house was just as charming -- if not more charming -- than the pictures. Super private but also great location with proximity to a CVS, grocery store and main street in East Hampton. Cindy was also very communicative and laid everything out super clearly with great recommendations etc. We are already planning our next trip!

We had such a wonderful stay at Ann Marie’s Airbnb! From the moment we booked, she was incredibly kind and responsive, making everything so easy and welcoming. The house itself was spotless, beautifully maintained, and had every amenity we could possibly need — it truly felt like a home away from home. The location was perfect — close enough to town that everything was easily accessible, but just far enough out that we avoided all of the typical Hamptons traffic. We even walked around the neighborhood every morning! We couldn’t have asked for a better balance of convenience and tranquility. Highly recommend this stay, as someone who frequents the hamptons — we’d come back in a heartbeat!

We enjoyed a lovely stay in the beautiful home. Josh was easy to reach and flexible with our requests.

🌟 A Perfect Hamptons Getaway – Highly Recommend! 🌟 We had the pleasure of staying at this beautiful Airbnb in the Hamptons for two days, and it was everything we hoped for and more. The home is a stunning blend of modern elegance and cozy charm. The interiors are tastefully decorated, creating a warm and inviting atmosphere. We especially loved the spacious living areas and the well-equipped kitchen, which made meal preparations a joy. Our host was exceptional responsive, accommodating, and genuinely kind. This Airbnb exceeded our expectations in every way.

Marta could not have been more accommodating! She was responsive and provided everything we needed. She even went the extra mile and insta cart-ed garbage bags and paper towels when we ran out. She could not have been a kinder host! We had the best weekend and would HIGHLY recommend staying at Marta’s place! We will definitely be back!

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.

Jason was a great host. Very responsive to any questions we had while staying on Shelter Island. The location is great - easy walk from the North Ferry and central to great restaurants. Airbnb was exactly as pictured. Would definitely stay again! Thanks again Jason!

Great stay! Very nice and accommodating host. I loved the fenced in yard and so did my toddler/dogs. The place is actually better then the photos. Will happily return in the future.

My two girlfriends and I stayed at Marianne’s house for a weekend escape, and it was absolutely perfect! The house was clean, cozy, and easy to find. I especially loved the peaceful morning walks to the nearby coffee shop. Marianne was incredibly responsive and offered great recommendations for things to do in the area. Thank you so much, Marianne – we had a wonderful time!

This was our second time staying at Ron’s place, and it was so great! The location is wonderful, the place is super dog friendly, the beach is perfect location. It’s a cute group of cottages down old Montauk highway, so away from the hustle and bustle but close enough for Ubers and driving! Can’t wait to stay again!

We absolutely loved our stay at Milton & Megan's Montauk house! It was perfect for a group of 4 (2 couples) there for a 4 day trip. The house is very quiet & peaceful, with lots of outdoor space, but also very walkable to town. The house was super clean, and everything was very easy to find. The bedrooms had lots of closet space, the TV was easy to set up, and all the amenities listed on the website were accurate. We'd love to come back again and stay. Thanks!

Karen’s house is comfortable and lovely. It felt very roomy. The kitchen was well stocked, even had much appreciated coffee and tea. Our dog enjoyed doing zoomies in the fenced back yard. I

Everything was perfect for our girls weekend. This is the 3rd time we’ve used Laurie’s house and there’s obviously a reason we keep coming back. Can’t wait to go again.

Our family had an amazing stay at Colleen’s place. Communication and instruction leading up to our stay was excellent. The location was great. The house was spacious, comfortable, and the pool was beautiful. The house is close to the beach and a short drive to Sag Harbor and the Hamptons. We had a fantastic time.

We had an amazing stay as usual. Thank you for allowing us to use this wonderful home.

Lovely place for a long weekend with family! The house was pristine, up to date, charming, and all the linens were fresh and clean. It was very well stocked with kitchen essentials and books and toys for kids. Location also prime with a private beach a 10 min walk away. The only minor issue we had was an issue with the pool heating (it being the 1st pool weekend of the year) but this was sorted out promptly. Would happily stay there again!

John was a perfect host! Friendly, responsive and made us feel welcome. I took my 9 year old son and we had a great time fishing off the dock and kayaking. The kitchenette is lacking if you want to cook any meals but it didn’t matter in our case. Absolutely beautiful location!

We had a lovely stay at Eric's home. The home exceeded our expectations and we felt right at home. The decor was warm and inviting. Everything you could possibly need was in the stunning, modern kitchen. The beds were all comfortable and we slept very well. The property was very peaceful. We enjoyed seeing deer, turkeys and hawks each day. The fixtures in the home were modern, clean and high-end. It was great being so close to Greenport with it's wonderful restaurants and shops. We can't wait to return.

We had a great time at Mark’s place! The backyard was quiet and beautiful - it was the perfect relaxing weekend for our group. We’d love to stay here again!

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!