18 Point Inner Way

This one-of-a-kind rental offers an unmatched Vineyard experience on the shores of Menemsha Pond. The estate’s main house features eight ensuite bedrooms, highlighted by a first-floor primary suite with two full bathrooms. The home is designed for entertaining on a grand scale, with two chef’s kitchens outfitted with top-tier appliances, a home theater with massage chairs, and generous indoor and outdoor living spaces overlooking the water.

Step outside to a showstopping waterfront setting with a sprawling mahogany deck featuring Italian outdoor seating for 20, an al fresco dining table for 24, a built-in Kalamazoo grill and pizza oven, a custom bar, stone fire pit, and two large Tucci umbrellas.

The separate pool house is a wellness retreat of its own, with a 10′ x 30′ indoor heated pool and spa enclosed by floor-to-ceiling glass doors that open to the outdoors, plus a sauna, steam room, wet bar, and two guest bedrooms. Upstairs, a full guest suite offers its own living room, washer/dryer, and two private balconies.

For those seeking inspiration, a hilltop writer’s cottage offers sweeping panoramic views of the pond. There’s also a separate entertainment building that includes a state-of-the-art Technogym fitness center, Peloton bike, full indoor basketball court with professional shooting machine, and a six-car garage with Porsche and Tesla chargers.