Vacation rentals with a hot tub in Southold

Stayed for a family wedding and loved the accommodations! Close to family, restaurants, wineries and beaches. Dog friendly which was a huge plus. Would love to stay again.

We loved our stay at Jimbo's. All the bedrooms are spacious and the beds are comfortable. The whole family enjoyed chilling out in the comfy sofas with a nice library in the living area. We all and in particular our dog loved the huge, green and well maintained lawn. He had so much fun with all the space to run and play! For us the greenery was very relaxing. The location is good - a 5 minute walk from the ice cream store, 12 minute walk from Crescent Beach (with the happening Sunset Beach Club), a 5 minute drive from the IGA, and a 5 minute drive from North Ferry. The furthest we had to drive was a 12 minute drive to Rams Head Point. The outdoor shower was lovely! Jimbo was very friendly and very responsive including providing some very efficient "tech support" on the dryer even though he was out of town. The issue was a confusing light on the dryer and some user error and was easily resolved on the phone. Additional towels were dropped off upon request. A pretty comprehensive set of silverware, plate settings, and kitchen utensils made it a fun and easy stay. Thank you Mary and Jimbo for sharing your house, we had precious moments there and we highly recommend it !

Such a great house for a group! Well kept and very accommodating. Will definitely be back

Kerry’s place was absolutely STUNNING! I mean truly breathtaking. The place was squeaky clean and had plenty of room for my group of 6. You can tell that Kerry put a lot of love and thought into everything. Although we didn’t have kids on this trip, I soooo appreciate that there were kid plates, a crib and even baby detergent; how thoughtful!! Do not hesitate to stay here; you will truly feel at home!!!! Kerry, you rock!

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.

Such a great stay! The place was perfect for a family weekend and everything was spotless upon arrival. Would definitely book again!

Cozy house that has lots of private and shared space. Clean, secure and updated. Shannon has the home thoughtfully appointed.

Exceeded expectations. perfectly functional and spacious. Great location...private, yet close enough to action.

We absolutely loved our springtime stay! Incredible space inside and outside that enabled our kids ample room to explore and have fun. Ann Marie was extremely responsive and went above and beyond to ensure our stay was memorable!

George was an excellent Air BnB host!!!! His responses were prompt and answered any questions we had. The location was ideal in Greenport as everything was walking distance. We had an amazing time!

Our family had a very enjoyable stay! The home and surroundings were beautiful, everything was extremely clean and organized, our host was wonderful! We absolutely loved the tea ceremony! It was very educational! We will definitely stay here again when we return to New Haven!

Very spacious house in charming town. Right next to hiking trails.