Martha’s Vineyard Vacation Rentals

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.