Vacation rentals with beach access in Southold

We had a great weekend at Nicholas’s place. It was very peaceful in the woods, and we enjoyed using the record player and looking through the books spread throughout the studio. Nicholas was very responsive when I texted with questions and we used his provided recommendations to find breakfast and dinner. We’d definitely stay here again!

“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!

Had a wonderful experience at Zoi’s place. It was very close to Main Street and was spacious and had everything we needed. I appreciated how there was already body wash/shampoo in the shower so we didn’t have to get it ourselves. Would definitely stay again.

this was my 4th time staying at this air b and b and as usual I dodnt want to leave!!. Sarah and Phil where amazing. I love going to this air b and b becouse its so peaceful and calm and its like be at home. I will be back again. if you looking for an awsome place to stay look no futher!!! this is thr place to go!! this family is wonderfully and beautiful people. I will be booking again. thank you again for being such an amazing host.. its like staying with family...thank you 😀😀😀..

I love this place. Perfect but what we were looking for. Walking distance to access beach. Overlooking the pier. Very clean and check in with.

Jason was a great host. Very responsive to any questions we had while staying on Shelter Island. The location is great - easy walk from the North Ferry and central to great restaurants. Airbnb was exactly as pictured. Would definitely stay again! Thanks again Jason!

Lovely place! We enjoyed our stay. So close to everything Greenport has to offer!

Wonderful and cozy apartment! We were in town for a wedding and needed a clean and safe space to make home base. This was perfect. Would absolutely stay again!

Beautiful house, perfect for a getaway to the north fork. Very close to a beach. Very clean and comfortable. Elizabeth is a great host. Highly recommend.

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!

Kristin’s house was perfect!!! It was even more beautiful in person and had absolutely everything we needed to have the best stay at Greenport! Not only was it beautiful, but it was also in the best location, making it easy to get to and from the Main Street and wineries! I traveled with 8 friends and we all said we’d book again without a doubt! Thank you Kristin for an unforgettable stay!

We had a great weekend in Mattituck! The house is in a great location close to the vineyards and we enjoyed relaxing in the beautiful backyard. It was a quiet and a peaceful escape from the city. Fabio was also a kind and informative host.

We had a wonderful stay at Ellen’s place. The house was beautiful and well appointed with anything you could need - it made us feel right at home. The backyard was gorgeous and relaxing. We were traveling with a toddler and Ellen made sure we had everything you could need for a child. The house had lots of room and was extremely comfortable. The neighborhood was beautiful and it was a quick drive to plenty of things to do. We could not have been happier with our stay!

Great stay! Very nice and accommodating host. I loved the fenced in yard and so did my toddler/dogs. The place is actually better then the photos. Will happily return in the future.

Yvonne's place is wonderful, we spent six days there on a family vacation to celebrate a graduation and it was a perfect spot for a crowd. The description and pictures are spot on (maybe even better) and the place is very well maintained. The weather was not great - so we landed up staying in more than we anticipated and this was a great spot for that. The kitchen is well stocked, having a barbecue really helped, and the large windows and skylights kept us connected to the outside. Yvonne was also highly responsive in case we needed anything. Highly recommend.

My husband and I have been staying here for over 10 years, and it’s always fantastic. The house is immaculate, cozy, and consistently well cared for. Judie and Steven are super thoughtful + welcoming, and the atmosphere is perfect for a relaxing weekend. Truly our favorite getaway spot! Can’t wait for the next one!

John and Cathy are amazing hosts. This was our second consecutive summer stay in their condo and it does not disappoint. The place and the amenities they provide are amazing and they are a wonderful couple who respects your privacy but are there for anything you need. I recommend anyone to stay here and know they would want to return. Thank you John and Cathy for making our second summer with you a fantastic vacation!

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.

We had a great time at Julie’s place. Would love to visit again…perhaps in the Fall. Loved the balcony overlooking the Sound. Julie was very responsive to my questions. She got back to me immediately. I would highly recommend Julie’s home!

Stay was great and the place was very clean

Had an amazing stay in Greenport. The condo was exactly as listed, extremely clean and has a ton of amenities. Tom communicated from when the reservation was booked until the end, he was readily available, answered quickly and gave tons of informations. The location is ideal with the private beach and pool and a quick 5 minute drive into town. The condo offers a great little kitchen, a wonderful balcony with a water view and an unbeatable sunset and all the amenities you need for your stay. Pool towels are provided, plenty of bathroom towels, there’s a coffee machine, 3 tvs, a variety of dishware and there’s coin operated laundry in the basement. The staff that works the grounds and property are also super friendly. The town of Greenport and other surrounding towns are all close, you have endless options for vineyards in close vicinity and there’s tons of amazing restaurants within a 5-15 minute car ride. I highly recommend booking this property, I will definitely be rebooking! (If yo

Beautiful stay at Cliffside! The photos don’t do it any justice!! The rooms were super clean and well decorated. Pool was great!! The beach was beautiful!!!! Loved this place!