Martha’s Vineyard Vacation Rentals
byPoint B Realty
In Wendy and Win’s collection of Martha’s Vineyard estates, you’ll find the perfect blend of luxurious amenities and coastal charm just minutes from the island's sandy beaches and charming harbor towns. From newly built, architect-designed homes and grand Colonial compounds to modern farmhouses and coastal chic retreats, each property is a masterpiece with no detail overlooked.
Inside, expansive great rooms with vaulted ceilings, vintage beams, and custom furnishings are anchored by chef’s kitchens with high-end appliances, wine fridges, and walk-in pantries. Every room is crafted for comfort and elegance, with features like large windows framing meadow views, comfortable high-end sofas, and cozy floor-to-ceiling stone fireplaces for chilly evenings. Luxurious primary suites, sun-filled family rooms, and state-of-the-art media rooms are all par for the course.
Thoughtfully designed for indoor-outdoor living and entertaining, you’ll find outdoor spaces that are an experience in themselves. Spacious mahogany decks and bluestone patios surround deluxe heated gunite pools and hot tubs, set on picturesque plots of land. Take a dip in a saltwater pool surrounded by wildflowers, enjoy an evening around a wood-burning fireplace in an outdoor living room, or dine al fresco under a pergola.
In the Point B collection, every space is professionally designed to maximize the beauty of island living. Unique touches elevate your stay with the perfect balance of style, comfort, and high-end amenities, inviting you to immerse yourself in the beauty of Martha’s Vineyard.
Doyen of Point B Realty
Wendy Harman & Win Baker
Favorite Restaurants
Outermost Inn, Detente, Beach RoadFavorite Brewery
Bad MarthaFavorite Bakery
Morning Glory Farm, Grey Barn & FarmFavorite Coffee
Catboat Coffee CoFavorite Beaches
Long Point Beach, Lucy Vincent BeachFavorite Things to Do on Martha’s Vineyard
Going out on the water on a catboat, sunset cruises on a Black Dog Tallship, nature walks through conservation areas, and al fresco clam bakes on the beachWhen Wendy Harman first visited Martha’s Vineyard in 1992, she was instantly captivated by its magic. She returned summer after summer until she finally took the leap – quitting her job and moving there full-time. With years of experience in real estate and vacation rentals, Wendy and her husband Win, started Point B Realty in 2008 to share their deep love for the island with others.
What sets Point B apart is its commitment to delivering boutique, white-glove service that goes far beyond a typical vacation. They exclusively manage a curated collection of around 100 hand-picked properties, partnering with like-minded owners who prioritize the guest experience as much as they do. Their team knows the island, the business, and their properties inside out and backward, allowing them to provide truly personalized service.
With a blend of cutting-edge technology and hands-on hospitality, Wendy and Win’s team handles every detail to ensure guests feel cared for from start to finish. It begins with personal pre-arrival phone calls, continues with a warm welcome at their high-end office – designed to set the tone with its beachy vibe and designer furnishings – and extends through every aspect of their stay, making the experience seamless and luxurious.
From the picturesque rolling hills of the western end in Chilmark and Aquinnah to the charming streets of Edgartown, Wendy and Win understand that the Vineyard is an experience all its own. Whether it’s matching guests with the perfect home, arranging special touches like grocery deliveries, oyster farm tours, and farm-to-table dinners, or highlighting local businesses they’ll enjoy, the Point B team makes it their mission to deliver the experience each individual guest is looking for. Their passion for Martha’s Vineyard is woven into everything they do, ensuring that guests don’t just visit, but return year after year.
Located in the Atlantic Ocean just south of Cape Cod, Massachusetts, Martha’s Vineyard is a picturesque island brimming with charming harbor towns and whaling villages, dotted with historic lighthouses and boat-filled harbors, filled with family-friendly attractions, walkable downtown areas, nature preserves, and boutique shopping, and – of course – surrounded by miles of breathtaking beaches, each one different from the next.
That’s why Wendy Harman and Win Baker, Owners of Point B Realty, are proud to call Martha's Vineyard home.