Monthly Rentals in Southold

Loved Kenneth’s house. Perfect for my wife & I to get away and explore the north fork for a weekend. Great location Private house Clean Comfy Walkable to Kenneys beautiful beach sunset Drivable/uberable to key winery or Greenport locations if needed Exactly what we were looking for as a mini couples getaway Would highly recommend; likely a returning customer Kenneth was responsive and pleasant with clear instruction 5 stars!

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!

We had a great stay at Todd’s house in Laughing Waters. The house is spacious, comfortable and well equipped. Some areas of the house could use a little sprucing up. Good set up for remote work. It is what is outside that makes Todd’s place special—proximity to the small beach nearby (a great spot for young children), the quiet neighborhood, the water view from the deck and the large yard and garden. Great place to walk/run, bike ride, kayak and swim. Quick drive to downtown Southold, Southold Seafood Market, Country View Farm Stand, the Southold dog park and several Vineyards. Over the course of our long stay we had a few minor issues and several questions. Todd responded quickly and in one instance sent his property manager over.

We had a wonderful stay! The master suite is huge and the bathroom is dreamy. We didn’t really use the backyard bc it was winter but it was great for our pup! Kitchen was small but did the job (no microwave). We had issues with streaming on the “guest” accounts but we always travel with our own firestick so we were fine. The beds were super comfortable (firm memory foam type) but it was quite bright in the upstairs bedrooms in the morning bc several of the windows had no covering so if you need a blackout situation for little ones pack accordingly. We were able to put the provided pack and play in the closet which was fine for us! We would definitely recommend and return!