House vacation rentals in Southampton

Joe's place was perfect for a girl's trip with two 1 year olds. The house was beautiful and had so much personality and warmth. The area was super private and quiet surrounded by nature. Joe was very informative about check in process and recommendations were plentiful.

I stayed at Ashton's place by myself on a visit to see my parents, who also live in Springs. It was everything I could have hoped for. So peaceful, and such a beautiful space. Amazing high ceilings and natural light. The yard is gorgeous, so I can only imagine how lovely it is when the weather is warm. Ashton himself is very responsive and accommodating. I was sad to leave!

House was stunningly beautiful, very clean. Pool was sparkling with lovely seating areas around it. Our 3 generation family enjoyed our stay immensely. Joseph and Tabitha were wonderful hosts. Very responsive. A charming home and an excellent vacation destination

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!

Dorina’s home was the calm, peaceful reprieve from the city we were looking for. Her home was so comfortable and she went above and beyond to make sure we had everything we needed. The backyard was a little oasis with a large pool (with floats!), several (6 I think) lounger chairs, two 6 top tables in different areas and a functioning grill. We spent most of our time here! Dorina was fast to respond, helpful with recommendations and overall what you hope to have in a host. We would definitely come back to Dorina’s home!

This house was fantastic! We cooked a full Thanksgiving dinner here! The house was well stocked with everything we needed, from kitchen essentials to paper products. The layout of the house was great. Jane was very accommodating and made things easy for us! The house was immaculate and met all of our needs. I hope it’s available next Thanksgiving! Perfect location! Close to town, yet quiet and private! It was my granddaughter’s first Thanksgiving and I’m so glad we had this house to celebrate in!

I had an amazing experience staying at this Airbnb! Luz, the main host, was absolutely wonderful—so kind, welcoming, and incredibly helpful throughout my stay. She went above and beyond to make sure I had everything I needed and even took the time to recommend some great local spots to visit. Her hospitality truly made this stay special. David was also fantastic so professional and accommodating. He made everything so easy, from check-in to answering any questions I had during my stay. It’s clear he takes pride in ensuring guests have a great experience. The space was spotless, beautifully decorated, and just as described in the listing. It felt so cozy and inviting, and the little details, like the complimentary snacks and toiletries, made all the difference. The location was also perfect. I couldn’t have asked for a better stay. Luz and David are a fantastic team. I highly recommend this Airbnb to anyone looking for a comfortable, welcoming, and enjoyable experience.

House is well represented. Spacious, very clean, and great location. Good for families or groups of friends.

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!

First off, Brian was one of the most communicative and helpful hosts I've ever had the pleasure of interacting with on Airbnb. He gave us clear and simple instructions for checking in/out, came to the rescue when we locked ourselves out of the house, shoveled our driveway after a big snow storm, and even found and offered to ship back important items we accidentally left behind. His place is truly a gem, exactly as pictured--beautifully decorated and meticulously curated. We had a wonderful time cooking in his well stocked kitchen--plenty of good pots/pans, oils and seasonings, knifes and good cutting boards. This kitchen is the real deal. And oh my, the master bathroom is incredible! The backyard is huge and fenced in, my dog loved running around back there. The hot tub is spacious, private and easy to operate. This house has everything you need for a good time with friends but beware the internet was super slow and my phone reception wasn't great so just be prepared for that.

Eduard’s place was wonderful! 6 of us gathered for the new year and there was plenty of room for all of us and one pup. The hot tub was excellent, and the landscaping was beautiful. The surrounding area was quiet and lovely. The den was a great area to relax and play games in. We’d definitely recommend staying here.

We had the best time in East Hampton at Carl’s. Lovely spot in an amazing location. We hope to be back!

We had an amazing time staying at this house! It was in a great location, well-stocked with everything we needed, and the host was incredibly responsive. The check-in process was seamless, making our stay even more enjoyable. My family and I had a wonderful experience, and we would definitely book again!

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 home is top notch!! Esther is truly amazing and everything was excellent. The kitchen is amazing, the basement play area was awesome and the rooms were perfect! I will be staying here again!

Alexis was a tremendous host-always available & great to interact with. The house was perfect, had anything & everything needed and was extremely comfortable. I would highly recommend her home to anyone visiting Shelter Island.

A great place to stay! Very enjoyable!

Kathy’s home was exactly as described spacious, clean, and incredibly inviting. I traveled with a large group of my friends, and we never felt on top of each other. Kathy was extremely accommodating & communicative when it came to checking in and checking out of the Airbnb,along with recommendations to eat on the island or close by. The home was an effortless walk to the beach and to center of town. If you were coming to enjoy fire Island with a large group of people, I would absolutely recommend this space!

My family and I had such a wonderful time at Chet’s home in Greenport. Perfect location, close enough to walk into town but also removed enough for privacy. Highly recommended!

Jillian’s was such a friendly host and very responsive! Her place so so charming. It was clean, warm, and welcoming. There were plenty of toys for the kids to play with, and a nice backyard with a fire pit to enjoy as well. The neighborhood was quiet and we were able to rest really well during our stay. We would love to return! Thank you Jillian!

Lovely, well kept and comfortably furnished. This home has everything you need for a comfortable stay. Owner is helpful and very responsive. Highly recommened!

Location was perfect for us- easy to find and close to things that are important to us (family in area, beach, shopping). Fenced yard made bringing our little dog that much easier- especially during the rainy day! Kitchen was well stocked thankfully as we were cooking Thanksgiving dinner (but not well stocked in the casserole dish, baking tin department-- which is usually not an issue for most people!). Decent coffee was supplied with a Keurig. Beds were comfortable. Everything was clean. I liked that he didn't leave a long list of what we needed to do before leaving as that is often a hardship when trying to leave a house with kids before a long drive. I would definitely stay here again.

Kate's place is an absolute gem! This was our first time to Shelter Island, and we loved the laid-back atmosphere. Kate's home has everything you need to have a relaxing weekend, from the amazing, heated pool to the kayaks on the beach, a 2-minute walk from the house! Having been in the hospitality business for over 25 years I tend to be super critical about cleanliness and amenities offered.....this house does not disappoint! We were a group of 10 attending a winery dinner and decided to stay for the weekend. We only left the house to attend the dinner, the rest of the time we stayed at the house, either in the pool, on the deck BBQing or inside chatting where there are two living rooms and a very well-equipped kitchen. The bedrooms were nicely decorated and comfortable! We would definitely recommend and hope to stay again. :)

We had such a wonderful stay here over New Years. Like many other reviews have stated, pictures do not do this home justice. It’s so much larger and more spread out than we expected. Perfect layout for two couples where we each felt like we had our own place, with plenty of cozy spaces to hang out too. The kitchen is SO well equipped for anything and everything. Beds and sofas were super comfortable and the we loved all of the charming touches of this historical home. The location is fantastic too. Walking distance to everything you could need and a quick drive to so many beautiful areas. I can imagine spending hours in the backyard when the weather is warmer too!