Vacation rentals with a hot tub in Shelter Island Heights

Ashley’s place was absolutely incredible for our girls weekend in Montauk. Impeccably clean, spacious, and tastefully furnished. The hot tub was perfect after a winter hike, and the firepit was great for s’mores and stargazing at night. There was also an indoor fireplace in the living room where we had a couple of really fun movie nights. The kitchen is a dream, and very well equipped with everything you would ever need to cook a fabulous meal. The spacious open plan kitchen/dining area/living room was perfect for communal cooking and hanging out. Gets great light and such a pretty view. The bedrooms were super comfortable and the master has an amazing tub. The location was perfect. Right in town and a short walk to the beach (also walking distance to the brewery!), but also felt very private. Lastly, Ashley was an excellent host- very communicative and helpful and super sweet- she even left a treat for us in the fridge when we arrived! Will definitely be coming back to stay at

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 !

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!

We had a wonderful stay at Jennifer’s place. It was.l beautiful, immaculate, and incredibly well equipped—especially for kids with the plethora of games and toys. Jennifer was responsive and a great host. The house is on a serene, dead-end street, and outdoor area is perfect for kids.

Our family had an amazing stay at this location. Loved that all the switches were clearly labeled as we have had trouble figuring out lighting in other locations. What a great touch! Wonderful yard and the basement was fun for all ages. This location was perfect for us as we have family all over the island. Lots of stores locally for anything you need. Highly recommend!

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.

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!

We had a lovely stay this April. House was spotless and newly refurbished. Pool area great (early in season so braved a cold plunge!!!) and appreciated the separate hot tub too. Pool furniture all brand new and special mention of the best kitted out games room I have ever seen! Location great. Very quiet but short car ride to East Hampton proper. Sammi’s beach a 10 min walk away. A fantastic stay and would not hesitate to recommend to others.

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