Martha’s Vineyard Vacation Rentals

What Makes This Place Special

Welcome to the Guest House at 40 Orchard Road, a charming and thoughtfully designed standalone retreat offering guests a perfect blend of privacy, comfort, and classic Martha’s Vineyard tranquility. Located on a beautiful multi-acre West Tisbury estate yet rented entirely on its own, this home provides an ideal escape for couples, small families, or friends seeking a relaxing island stay in a peaceful setting.

Welcome to a Vineyard Haven home designed for families who want to vacation together without feeling crowded. Located near downtown, the ferry, restaurants, shops, and Owen Park, this six-bedroom property combines the warmth of a classic Island home with an updated kitchen, refreshed bathrooms, central air conditioning, and plenty of space to gather. The bright kitchen offers generous room for preparing family meals, while the dining area seats up to thirteen. Several separate living spaces—including a comfortable den, sunroom, library, and ping-pong room—give adults and children room to relax, read, play, or spend time together. Outside, the half-acre property feels leafy and private, with mature landscaping, a fire pit, hammock, gas grill, picnic tables, outdoor shower, and a tucked-away secret garden. After a day at the beach, rinse off outdoors, settle into an Adirondack chair, and enjoy a quieter side of Vineyard Haven life. With six bedrooms, four bathrooms, central air, two Smart TVs, laundry, and beach equipment, the home is especially well suited to extended and multi-generational families seeking comfort, convenience, and an authentic Martha’s Vineyard setting.

Discover the charm, comfort, and unbeatable convenience of 22 Grove Avenue, a gracious historic home in the heart of Vineyard Haven—just off Main Street and a quick three-minute stroll to ocean swimming at the bottom of the street. This beautifully cared-for property blends classic Vineyard character with modern amenities, making it an ideal retreat for extended families, multi-generational groups, and anyone who wants to experience Martha’s Vineyard at its most accessible and welcoming.

Available weeks are listed for your convenience. Turnover days may adjust depending on the calendar, and minimum night stays may apply during high-demand weeks. I’m happy to answer any questions or help with booking — please reach out to Ashley Killian at Ashley@portfoliopropertiesmv.com.

Set near the water with direct access to island living, this property offers an easy coastal rhythm from the moment you arrive. Located on salt water and within walking distance to a saltwater beach, days naturally begin with beach walks and end with outdoor showers and relaxed evenings at home. Outdoor living is a highlight here, with a deck, porch, or patio for morning coffee and evening grilling, a private yard to spread out, and a BBQ grill ready for casual meals. After the beach, rinse off in the outdoor shower and settle into a space designed for comfort and convenience. Inside, the home is fully equipped for extended stays and effortless living. Enjoy reliable internet, cable/satellite TV, multiple TVs, and DVD access, along with A/C units, ceiling fans, and portable fans to keep the space comfortable throughout the summer. A washer and dryer are available, and the home is pet-considered and non-smoking. The kitchen is stocked for real use, featuring a coffee maker, oven, stove, refrigerator, microwave, dishwasher, dishes, and utensils—everything needed to cook, entertain, or keep things simple. Accessibility is thoughtfully considered, with a first-floor bedroom and first-floor bathroom, making the layout easy for all ages.

Welcome to Seaview Condominium #203 at 2 Pennacook Avenue, a beautifully appointed coastal retreat offering elevated views and relaxed comfort in the heart of Oak Bluffs.

Welcome to your quintessential Edgartown escape — a thoughtfully updated 2-bedroom cottage tucked just moments from the heart of town. Located on quiet Silva Lane, this home offers the rare combination of village convenience, beach proximity, and comfortable, relaxed Vineyard style, all at a price point that makes summer on the island more accessible.

(To book this property, Available weeks are clearly listed. This home has a Sunday-Sunday turnover, so online bookings must begin and end on a Sunday. A minimum stay of 7 nights is required. Questions can be directed to Ashley Killian, Ashley@portfoliopropertiesmv.com)

Wake up overlooking Vineyard Sound at this classic Beach Road cottage, ideally positioned between Oak Bluffs and Vineyard Haven. Designed for a simple, relaxed Vineyard stay, the home offers a private rocky shoreline, a waterfront sitting porch, a separate sun deck and convenient access to nearby beaches and both harbor towns. Inside, the cottage retains its nostalgic island character while offering refreshed flooring, fresh paint and comfortable accommodations for up to four guests. Spend the morning by the water, explore the Island during the day and return for ocean breezes and sunset views from the deck.

The Property -Bedrooms & Baths: Four comfortable bedrooms, three full baths. Plus, if needed, additional attic loft sleeping space is available for extra guests. -Living Spaces: High ceilings, lots of windows, and vintage details like antique fir flooring, substantial trim, and “two‐over‐two” style windows with double hung shutters. The living room features a wood‐burning fireplace. -Kitchen & Dining: Fully updated with modern appliances (including a gas stove), teak counters, painted wood cabinetry, and wide plank pine flooring. Great for cooking or gathering. -Outdoor amenities: Private wood-deck areas and an outdoor shower to rinse off after beach days. -Comfort Features: Heating and, in some parts, cooling (central heat; attic and/or mini-split AC) to make stays in all seasons pleasant.

Welcome to Arrowsmith Cottage – a clean, comfortable and casually stylish home base for a carefree Martha's Vineyard vacation, any time of year.