Beachfront holiday rentals in Southold

“A Wonderful Stay!” I had such a pleasant experience at this Airbnb! The space was clean, cozy, and exactly as described. The host was incredibly welcoming and attentive, making sure I had everything I needed for a comfortable stay. The location was perfect—quiet and peaceful, yet close to everything I needed. I especially appreciated the thoughtful touches throughout the space, which made it feel like home. I wouldn’t hesitate to book again—highly recommend! Feel free to customize it with any specific details about your stay!

We very much enjoyed staying in Meredith’s place. The cottage is surrounded by trees so it feels secluded and peaceful. The cottage is elegantly decorated; there were so many nice books around which we enjoyed checking out. Meredith was so nice and responsive. We will definitely go back.

This home is just as advertised. The home had lots of extra amenities and the kitchen is very well stocked. The home is beautiful inside and has plenty of space for 4 people. The home has been remodel and they did an excellent job of incorporating the old with new modern conveniences. We would recommend this home to anyone and would love to stay there again if we are ever back to Greenport.

Ashley’s house is the perfect get away. I booked this house for my family to stay for my wedding weekend. My mom had never stayed in an Airbnb before and I’ve never seen her so happy and relaxed. She truly enjoyed her first Airbnb experience at Ashley’s place. It was exactly as described and the view is beautiful. Ashley was very responsive and made sure to answer any questions I had.

Completely great place! Looked like the photos but even better! Super responsive! Great stay

Spent to my birthday here with my husband, dogs and toddler. Had my gender reveal birthday cake, outback under the sunset. Truly magical.✨ The backyard was ideal. Was able to tie the dogs to the deck with a 20 foot leash. It kept them contained to the backyard & away from beach goers on foot and other dogs. The dunes kept the backyard private you’re not staring at your neighbors. Felt so secluded. I also have some mobility issues and you couldn’t ask for an easier way to enjoy the beach & get your toes in the sand. The house & deck are spacious and easy to navigate with a walker. Was able to add extra days to our stay. Would 100% stay here again.

First trip to the North Fork and loved every minute. Deb's cottage was just what we needed and she was the perfect host. We'll be back!

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

We loved the location and the place was beautiful. Its was nice and clean. Definitely will be booking again

An amazing stay overall. It was comfortable for 6 adults. Spencer was extremely helpful throughout our stay — I had lots of questions and Spencer was quickly responsive. The house itself is beautiful and has that eastern Long Island charm. The backyard had lots of space and is well maintained alongside the pool. We also enjoyed a sunset evening at the beach which is just a few steps away. It was a wonderful weekend and I am certainly looking forward to staying here in the future!

Great retreat for a long weekend. Enough space for family of four. Easy access to everything in the Greenport area. Mia was very responsive, and the place was great. We would stay here again!

If we don't give a good review, can we keep this to ourselves?! Patti was a perfect host; the views were fantastic, whether from the outdoor porch or inside through the French doors looking out on the water. Access to the small beach and pool were excellent and we were close to several good restaurants (many of which Patti suggested, including some on the water) for take-out during the pandemic. Wifi was great and everything was very clean and as advertised. We generally fly for vacations and long weekends but had to stay closer to home this year and this was a perfect choice.

Gorgeous house and property that is even better than the photos. Like other reviews have mentioned, the highway noise in the backyard is definitely present, but easy enough to ignore. Really enjoyed our stay and communication was great!

Donald was an excellent host - he was super responsive, checked us into the house himself, and offered tons of recommendations of things to do for the weekend. The house was incredible and our group had so much fun - the pool, hot tub, outside deck and overall space was great. 10/10 stay!

Great and responsive host. Home was lovely and we felt welcome. Host responded quickly to questions and requests. The home was very peaceful and relaxing. We really enjoyed the outdoor patio and pool area. I would recommend for a peaceful time away from the city.

We had a great stay at Kelsey's place with our family. The location was fantastic - walking distance to the town! Very clean and thoughtfully laid out with seating in the back - and a heater and a fan to accommodate any weather and we sat out there and enjoyed when we were at the house. Kelsey was very responsive and lovely to work with.

This place was divine. We came for a week with our two kids (4&6) and had the easiest most laid back time. We kayaked, walked to the beach, the kids played constantly around the house as it’s right on the water but the yard is fenced off. It was so good you guys 10/10 would book again. And Jeff was the best host. So quick to respond, provide options etc. He rocks.

I had a fantastic stay! The property was exactly as described—clean, comfortable, and located in a great neighborhood. Check-in was smooth, and the host was communicative and welcoming throughout my stay. The space had everything I needed, from thoughtful touches to all the essentials. I’d absolutely stay here again and highly recommend it to anyone visiting the area. Thank you for a great experience!

We were very pleased with AJ’s place. We are 2 friends that came to cycle and explore. Location was good. Nice to each have a king bed. Can walk to beach.

The place is lovely and as expected from the ad. Everything went smoothly. Highly recommend

We had a lovely time in Margaret’s cottage. It had everything we needed and we felt surrounded by nature. Our kids loved watching the squirrels, wild turkeys and other birds that were constantly going back and forth in front of our windows.

Lovely gem, right in new haven, You get a beach built into the house, lovely sand. You get the peaceful surrounding and a great house with great amenities to enjoy like a firepit, a kids slide & swing and a barbeque. You get the ability to order in food from any variety of restaurant from new haven. You get a nice host that helps you all along the way All in all great choice for a relaxing walkaway.

We enjoyed our stay at Sue's and Danny's place. The beach is very special with beautiful sunsets, and the cabin is equipped with everything we needed for our stay. A great weekend getaway!

John’s place is absolutely stunning! The deck and the dock made for beautiful mornings with coffee and evenings with wine. It’s a short drive from a few beaches or to the ferry to fire island. Overall would definitely stay again!