Family-friendly holiday rentals in Orient

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!

We thoroughly enjoyed our time at the cottage. It was so very peaceful and we loved being literally right around n the water! Slept amazingly well and the cottage was just lovely! Robert was also a great host. 5 stars all around and we hope to return again!

We had a fantastic girls weekend in Southampton and loved Anthony's cottage. It was so beautifully decorated and cozy. We throughly enjoyed mornings with coffee and books in the sun room.

Had booked a girls getaway at Tracy and Patrick’s place and it was perfect, even with gloomy weather! The house perfectly matches all pictures and descriptions and has everything you’ll need and more for the perfect relaxing and fun getaway! We even got a cute surprise visit from their furry friends which is always loved!! There are also shops and beaches a short drive away, we just didn’t happen to go visit because we were enjoying our cozy time at the home. Thank you again Tracy and Patrick:) we would totally recommend and want to come back!

Fantastic absolutely amazing experience. Jaime was beyond great when it came to professionalism and kindness and responsiveness. Super clean beautiful apartment didn’t miss a trick when it came to anything you might need. This was a top-notch experience. Amazing customer service, beautiful location. Beautiful pool and spa overlooking the ocean We will definitely be back.

This was a great find for a long weekend! It was perfect for our dog as the front- and backyards are fenced in. Wonderful kitchen, great pool and close to town which made for a perfect stay. Cindy gives good recommendations on restaurants and activities and is very responsive if you have any questions.

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!

Beautiful, relaxing, clean Airbnb. Had an issue with the shower, which can happen anywhere, Mk was super responsive and came over quickly. Loved loved loved our stay here. Didn’t use the swimming pool due to weather but the screened deck with the Fire Pit and the superb game room saved the day. Thank you for hosting us will be back

Kate and Daniel are wonderful! Their beach cottage is a must for all families. The farmers markets within 2 miles have all the produce you need, while the fish markets within 5 miles have all the fresh caught seafood you need! There are several New York vineyards nearby and I’d recommend traveling to all the local towns like Greenport, Shelter Island, West/East/South Hampton, and Montauk to see how each one has its own identity. Overall, my wife and I loved our stay at the cottage and we spent most are days laying on the back porch with the beautiful views! Also, great kitchen for cooking and backyard grill with a view.

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!

This place checked all the boxes. Very clean and comfortable home and a short uber ride to downtown Sag Harbor. Nice big yard for relaxing after a long day on the boat. Will definitely stay here again. Great host and a great place

We loved our stay! It was one of the coolest Airbnb stays our family has enjoyed. Lots of art and ambiance while also being very comfortable with all the amenities you could need. It is an open space (the bedroom walls don’t extend all the way to the ceiling), which didn’t bother us at all but something to be aware of. Thank you Pam!

We had a wonderful family stay a this home to visit some local kid attractions including the aquarium. Hope is a fantastic host - great communication, friendly and accommodating. The house itself was roomy for our group. It was clean and very well appointed with all the basics you need to be comfortable. The four king sized beds was really nice. No fighting over rooms! Our kids enjoyed the chalk and bubbles that were left outside and playing in the yard. The deck is also a nice space although we didn’t get to use it due to weather. I would definitely recommend this home.

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 had a great stay for our first trip to Hampton Bays. It was our first time visiting and we loved everything about it. The neighborhood is peaceful and quiet. There are three restaurants that we loved within a mile. The backyard patio is a peaceful place to spend the afternoon or an evening. Thank you!

Great place,very convenient for entire extended family to be in town for college graduation weekend. Very large and open common area and kitchen for gathering for meals and celebrating all together.

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.

The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!

Christine's place was nice and clean! We especially loved the fire pit and the pool. Upon arrival of the AirBNB Christine was waiting to meet us and show us around. This was something that was new to me in my AirBNB experience, but it was honestly so nice and so was she! Christine let me know that I could communicate with her for anything that was needed and asked for recommendations to make her place better. This place was so well-equipped, close to everything and it comfortably fit me and my 6 other friends! I would definitely book again with Christine.

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!

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!

Ed was a great, communicative host, and the place was cozy for four of us during a week-long work trip!

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!