Holiday rentals with outdoor seating in Amagansett

My family had a wonderful time at Robert’s home. The house was clean and cozy and the view of the water was peaceful. He was super communicative and friendly and check in/out was a breeze. The house is in a great area and super close to East Hampton, Amagansett, and Montauk. Highly recommend!

We loved our stay at Deborah and David's home. The house was perfect for our family, so clean and well equipped. It is even better than on the photos. And what an amazing backyard for the kids!

Maher’s house was an amazing peaceful experience. I enjoyed my time there and he had great recommendations to restaurants and activities! He was very responsive with all questions we had. I will totally stay here in the future if I can get the chance again!! Thank you Maher!!

I stayed here with friends for my bachelorette party and we had the best time! The house was adorable and so comfortable! The back yard was amazing and the little guest house was so cute. Our stay was in mid April, so still a bit cool for fully using the back yard, but I bet in the summer it’s even more amazing! Everything was really clean and tidy and just a nice atmosphere overall. The house was a quick drive to the town area which was great! Paula was communicative and a helpful host! Really enjoyed our visit so much!

We had another great stay at Claudia's place! This was our third visit to this location, and likely not our last. Thank you!!

My stay here was phenomenal! From the host’s response time, down to the amenities that were placed throughout the house. As soon as you walk in, it felt like home. The house is spacious and highly functional. The design of the house offers a perfect blend of modern mixed with nostalgic elements. The best stay by far. Would love to book again!

This was our second stay at Judie's place. The house is immaculately clean, from easy check in, instructions left, comfortable beds, location is amazing, walkable into town. Showers are great, I could go on and on about how great the space is. We will definitely stay here again when back in Greenport.

We planned a moms weekend away at Chris’ house and the accommodations were great! Easily fit 8 women comfortably. The only issue was figuring out the heat (it was a fancy thermostat) and definitely could have used a larger coffee pot and more mugs for the amount of people. Otherwise, all good and we would definitely consider booking again!

We had an amazing stay! The space was spotless, cozy, and exactly as described—if not better. Nick was incredibly welcoming and responsive, making the whole experience smooth and stress-free. The location was perfect for everything we wanted to do, and all the little touches (like fresh towels, coffee, and local tips) made it feel like a home away from home. I’d absolutely stay here again and highly recommend it to anyone visiting the area!

The apartment was super clean and spacious! Has everything you need. Walkable to town and in a quiet neighborhood. Would definitely recommend Amanda’s place and would 100% stay here again!!

Great spot! Very walkable. It's also a great layout if traveling with small children - there is a separate meditation room upstairs that was perfect for setting up our travel cribs. Would stay again!

My friend and I stayed at Clare’s Airbnb in Montauk over the weekend, and she was one the nicest and most attentive hosts we have stayed with. Our room was really nice and contained everything we needed to have a very comfortable time. We really appreciated Clare for her very friendly hospitality and for going above and beyond for us whenever we needed her for something. And she was so lovely to our dog, Chi Chi ☺️ We will def stay at her place again if we make another visit to Montauk! 🐶🐾💕

This place was a gem! Roomy and spotless, just perfect for a long weekend in the Hamptons. Have stayed in several other airbnbs in the area over the past few years, this one was the best by far. Very accurate description and photos, comfy, super responsive host, well equipped, easy to get to town. Would definitely stay again!

Claire's place was the perfect spot for a weekend getaway. It was very clean, cozy and nicely situated on a peaceful street in walking distance to the LIRR train station, the main street in Southold, and a lovely beach with stunning views of the Shelter Island Sound and its surroundings. I would definitely book again!

Lovely, clean, comfortable, well-designed space. Hosts are friendly, responsive, and respectful of guests’ privacy. Would stay again!

Great stay at a great location

Mark's place was exactly what I was looking for to ring in the New Year in style, comfort and complete relaxation! I was able to start each day with a quiet cup of coffee and then head directly to the beach for a long morning walk (just a short drive away). Montauk Manor is an absolute hidden gem for a winter break and the indoor pool and hot tub are a rare find in the Hamptons. Check-in/out could not have been any easier and the Manor staff are wonderfully welcoming and friendly. There were still a good number of local shops open, including Left Hand Coffee. 100% recommend for all seasons and will eagerly book again!

We very much enjoyed our stay at the Cliffside for our wedding weekend! Alice was very flexible with us, which we appreciated because getting married is chaotic enough LOL. Would highly recommend staying here. The unit was spotless and had a wonderful view. We could not have asked for a better stay!

Just as described, beautiful waterfront location that’s a 5 minute drive to town and local vineyards. Perfect weekend getaway

Absolutely wonderful stay and host. I've stayed at dozens of Airbnbs and this is one of my favorites! Doug's place is even better in person than the photos. We were a little nervous taking our first trip away with our baby, but it was extremely clean and comfortable, and Doug was so kind and responsive. The condo complex has a lovely boardwalk for taking walks, and the deck furniture was so comfortable to lounge in and take in the beautiful view. We hope to be back!

We really enjoyed staying at Lynn’s place! Very clean and had a great view of the ocean from the deck. Lynn was very responsive and made the experience seamless. We would definitely stay with Lynn again.

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+

The place was perfect nice and clean what I like the best is the it was close to the beach to go for a walk.

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!