Summary:

Circuit Breeze, Sand By Me & Whale Tail Retreat



The Space:

Experience the ultimate Martha’s Vineyard getaway by booking all three unique residences—Circuit Breeze (3A), Stand By Me (3B), and Whale Tail (3C)—together as one expansive, multi-level retreat in the heart of Oak Bluffs. Perfectly positioned in and above an iconic gingerbread building directly next to Vineyard Vines, this rare offering combines historic island charm with modern comfort in an unbeatable downtown location.



Spanning both the first and second floors, this 3-unit setup is ideal for larger groups, extended families, or multiple couples traveling together—offering the perfect balance of shared space and private retreats.



The upper-level condos (3B & 3C) have been beautifully reimagined from top to bottom, featuring bright coastal interiors with crisp nickel gap walls, central A/C and heat, and stunning quartz kitchens with brand-new stainless steel appliances. These thoughtfully designed spaces include spacious king bedrooms, stylish living areas, and dining spaces perfect for gathering after a day on the island.



On the first floor, Circuit Breeze (3A) offers a relaxed and inviting atmosphere with comfortable living space, a fully equipped kitchen, dining area, and convenient access to a private outdoor seating area—perfect for morning coffee or unwinding in the fresh island air. With a mix of king, queen, full, and sleeper sofa accommodations across all three units, the property comfortably hosts larger groups while maintaining flexibility and comfort.



Across the full property, guests will enjoy multiple living areas, three full kitchens, in-home laundry, smart TVs, Wi-Fi, and all the everyday essentials needed for a seamless stay from arrival to departure.



Step outside and you’re immediately immersed in the energy of Oak Bluffs. Located right on Circuit Avenue, you’re just steps from boutique shopping, top local restaurants, and lively nightlife. The harbor and ferry are a short walk away, making arrivals and day trips effortless, while nearby Inkwell Beach offers the perfect spot to relax by the water. Just beyond, the historic Campground Cottages provide the colorful, storybook charm that makes this neighborhood one of the most beloved destinations on the island.



Whether you’re starting your morning with coffee on the porch, spending the day exploring beaches and shops, or gathering together in the evening after a sunset by the harbor, this 3A–3C Coastal Retreat offers the perfect combination of location, style, and space—creating an unforgettable Martha’s Vineyard escape for your entire group.