Beachfront holiday rentals in Southold

This house is a gem! I came to stay a week in off season with my dog, Rollo. The location is breathtaking, right on the Long Island Sound. We had a great time exploring the beach, looking for all the biodiversity in the birds and sea creatures, watching the boats, and this place is relatively close to an airport so watching the planes land and take off was awsome as well. We came for privacy, and I expected the beach to be a little more private than it was due to my dog's reactivity. But the neighbors did not seem to have issues with us, and once you are close to the water, especially in low tide, the beach is pretty open for all the locals. Walking around, the locals all waved and said hello. Not too many restaurants close by, but the Lobster Shack down the road had good food! Would stay again! The deck alone was worth it!

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.

I had a very nice stay at the Rex. It is dog friendly and very clean. Although my space was private, there are other rentals nearby and it had a camp like feel. I would stay there again if need be.

We loved Laura and Dana’s Big Easy home by the beach. It was big and comfortable and every detail had been thought about to maximize our enjoyment. Drawers and closets and cabinets were all labeled so we didn’t have to search for anything or guess where anything was. Literally every need had been anticipated! Amazing. The beds and bedding and linens and towels were abundant and soft and comfortable. The kitchen amenities were awesome, from an air fryer, to a full set of bar tools and blender, to great appliances. The decor was happy and cheerful and creative and fun. There were so many places to sit and enjoy, both inside and out. Do not hesitate to choose this wonderful place for a visit of any length. You will love it!

Barbara’s place reminded me of the way airbnbs used to be. It felt like home-away-from-home. The accommodations were high quality and clean, and there were even some tasty snacks! We loved our stay. Everything was as pictured. Stony Creek was wonderful, and we look forward to visiting again next year!

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

I had the most amazing stay at this Airbnb beach house. The views were absolutely immaculate, turning every moment into a picture perfect scene. The property was not only impeccably clean but also radiated a sense of peacefulness that immediately helped me disconnect from the hustle of daily life. Every detail was thoughtfully curated from the comfortable bedding that guaranteed a night of uninterrupted sleep to the high quality toiletries that added a touch of luxury to my routine. The well-equipped kitchen made it easy to prepare meals whenever I wished, and the fast WiFi ensured that I could seamlessly blend work and leisure as needed. A true highlight was the friendly welcome with a customized snack basket that set a warm, personal tone right from the start. Additional amenities, such as a cozy fireplace perfect for evening gatherings, stylish decor that elevated the overall ambiance, and easy access to local attractions, truly made my stay unforgettable. I will be returning.

Loved our stay at Cameron’s in Milford! Location is within walking distance to the ocean and there were bigger beaches+parks near by (driving distance). Not much other than the beach to do in Milford but we managed to have fun plenty of fun and made lots of memories with our dogs!

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

Amazing time front of the ocean, enjoying time with kids and familly. The pool seems great but was too cold for us in this early time of the year.

Geoffrey and Thomas were very gracious hosts, filled with benevolence, they greeted us with such warmth, gave us a tour of their beautiful home, along with the complimentary beverages, providing us with resources as well as information about the island since we’re newcomers, the house was lovely, clean and serene, hot tub was amazing, we enjoyed hearing their stories about fire island as well as giving us recommendations for food, shopping and sightseeing, it’s good to know fellow New Yorkers will have your back, very happy we picked their place to stay, absolutely would come back.

Fantastic location! We were literally a two minute walk from the beach. The studio apartment was as advertised and we would stay there again. We highly recommend!

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!

We had a wonderful girls weekend at Allana’s house by the sea! When we had a small incident with the keypad, Allana was quick to answer my call and resolve the issue no problem. Everything was clean and beautiful! We especially enjoyed the screened in porch in the back to enjoy our meals. The view from the master bedroom and deck is incredible! We highly recommend and will be back!

Dan is the most responsive host we've ever had. Usually we got a reply within minutes or even seconds. He happily got the hot tub heated up for us when we needed it and replenished our towels within an hour of our request. That hospitality made our stay so much better. The home is beautiful! It's right on the water, and features lots of luxurious tile, a huge patio, a little dock and lots of windows and open space from which to see it all. We especially loved the hot tub. I wouldn't hesitate to stay again if I'm ever on Long Island again.

Loved Samy’s corner unit, which gave us a bit more privacy and quiet than other parts of the property. The studio was as described, with great light and well-cleaned prior to our arrival. Enjoyed use of the tennis courts every day. Only minor disappointment was that we were not yet allowed to use the pool, which we were told would be ready by Memorial Day (we were there one week prior). Still, a worthwhile stay and I’d come back and recommend it to others.

We had a wonderful stay at Eileen’s place. Many great restaurants close by…Lenny’s, Dockside and Rosso Vino we enjoyed. Delicious ice cream spots..Bishop’s Orchard Creamery and Ashley’s.

My husband, dog, and I LOVED our stay here- so much that Danielle accommodated for us to stay an additional day! It was the perfect location. Private enough where we felt secluded, but yet right off of a main road with so many great restaurants to walk to! The beach was about a 5 minute walk, and left us with the perfect spot and feeling like we had the beach completely to ourselves the days we were there. We are already talking about going back, and can’t wait to plan our next trip. Thanks so much!

As a native long islander I enjoy finding great properties I can bring my family to to take advantage of all long island has to offer. This was the DREAMIEST beach bungalow!! The bedroom with the two beds was just my favorite room especially since we visited off season. You cannot beat this location. I can't wait to book again during high season! Thanks for sharing your home with us !!

Had a lovely time in the Hamptons! Tasha was an amazing host- easiest check in/out, very responsive, and gave great recommendations for places in the area. Would love to stay here again!

Perfect place to unwind after a long day of exploring the North Fork 😍 Steps away from downtown Greenport and its charming restaurants, shops and bars. Not to mention we could find everything we needed and felt right at home in the beautifully appointed apartment :)

Super nice place good communication. All around worth it!

Nice place, 2 adults, 2 kids. Exceptional kitchen!

Our stay at the Secret Stone Cabin was truly unforgettable. The breathtaking views and thoughtful touches made it feel like a home away from home. It was a luxurious retreat, complete with extra amenities like plush bathrobes, quality toiletries, and a chef-style kitchen. We took the row boat for a short spin, and had the weather been nicer, we would have loved to enjoy the beautiful outdoor fireplace. Every detail was perfectly curated for comfort — we can’t wait to come back!