Vacation rentals with a hot tub in Shelter Island Heights

What an absolutely gorgeous home! Staying here truly felt like being in paradise. The house itself feels so inviting; it took no time at all to relax and feel at home. Everything that you could possibly need is here in the house. Michael’s attention to detail deserves praise! This home stands out from all others because of the minor details. Thank you, Mike, for giving me a safe, pristine, relaxing place to call home for a while. I look forward to staying here 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 !

I had a wonderful experience at Ashley's place! The location was fantastic, just a short walk from the aquarium, which was a huge plus. I brought my three dogs along, and we had a total of seven people in our group, all of whom fit comfortably in the space. Unfortunately, I accidentally broke a vase during my stay, but Ashley was incredibly nice and understanding about it. I truly appreciated her kindness throughout my visit. I highly recommend this Airbnb for anyone looking for a pet-friendly spot in a great area!

Stan is terrific! Flexible on both entry and exit and was very helpful with anything we needed. The place is perfect for kids, safe and fun and the hot tub was perfect for downtime at the house!

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

Absolutely beautiful home with every amenity and comfort. You can tell how much love and care went into this place- every piece of furniture and detail is the highest quality. It’s even more spacious and beautiful than it looks in the photos. It was perfect for our group with young kids and it was great they provided a pack and play so we didn’t have to pack one. The hosts were easy to communicate with and flexible. They even let us check out late on our final day. We opted to enjoy the beautiful yard and home longer rather than venture out because we were so comfortable. We cannot wait to come back in the summer as the pool and yard set up is incredible. Thank you for a wonderful stay!

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.

The house had stunning views from every room on all floors. The kitchen was well-equipped for our large family. The owner’s responses to questions about the property were prompt and helpful. We enjoyed the fire pit and hot tub since it was too early in the season for the swimming pool. My family agreed we would rent again if a reunion is planned.

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.