Homes For Rent

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,…

Welcome to 7 Mill Hill Farms Road, an exceptional Katama retreat designed for elevated summer living in Edgartown. Spacious, stylish, and thoughtfully appointed, this impressive home blends luxury finishes with relaxed indoor–outdoor living—creating the perfect setting for an unforgettable Martha’s Vineyard vacation. The home offers approximately 3,800 square feet of living space with multiple bedroom suites, providing privacy and comfort for families or groups traveling together.  Inside, the interiors are beautifully…

Welcome to 10 Eagles Nest, a relaxed and beautifully bright Edgartown getaway set in the sought-after Dodger’s Hole community—an easygoing, central island location known for its peaceful setting and convenient access to all three down-island towns. Inside, the home is designed for effortless vacation living: soaring ceilings, clean architectural lines, and abundant natural light create an airy, welcoming feel the moment you arrive. The open-concept main living space flows comfortably from living…

MORE 2027 AVAILIBILITY COMING SOON! Welcome to your ultimate Martha’s Vineyard retreat. Perfectly situated where Katama meets historic Edgartown (only 0.9 miles away!), this striking 5-bedroom, 3.5-bathroom modern farmhouse sits on several pristine, private acres—offering the rare combination of peaceful seclusion, expansive lawn space, and easy access to both South Beach (3.0 miles) and downtown Edgartown. The Space Architectural Grandeur & Living Step through the front entrance into a breathtaking double-height foyer…

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…

This property sits right on a bus route, so you can step outside and take the free VTA bus straight into Vineyard Haven, Oak Bluffs, or Edgartown with ease. Newly built, the complex unfolds as a four-bedroom home nestled into a building with an above-garage apartment, plus a separate two-bedroom guest house—designed for togetherness with space to spread out. Fresh paint, fresh linens, and brand-new kitchen appliances set the tone for a…

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. Wake up to serene views and easy island living at this bright and welcoming Oak Bluffs retreat. Nestled near local beaches, charming town spots, and scenic bike paths, this…

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. This thoughtfully furnished two-bedroom, two-bath residence blends contemporary style with easy Vineyard living. The open-concept living and dining area is filled with natural light and designed to highlight the surrounding water views, creating a bright and inviting space for gathering, relaxing, and unwinding after a day…

Welcome to 1 Essex Court, a comfortable and versatile Edgartown retreat designed for relaxed summer living and memorable gatherings. Located in the desirable Windsor Drive area, this well-maintained home offers generous indoor and outdoor spaces, making it easy for families and friends to return year after year. The heart of the home is an open living, kitchen, and dining area, where the island kitchen flows seamlessly into the main gathering space—ideal for…

Tucked into the heart of Chappaquiddick, this charming cottage offers a cozy queen loft, two twin beds, and an inviting deck with a grill and bistro lighting—all near the Royal and Ancient Golf Course.

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. This inviting guest house features two comfortable bedrooms…

Built in 1784 by Reverend Joseph "Parson" Thaxter, First Chaplain of the Revolutionary War and the town's longtime minister, this storied residence has anchored the island's history for more than 2 centuries. Today, it has been meticulously restored and thoughtfully updated to offer a one-of-a-kind Vineyard experience, blending heritage, elegance, and comfort in the heart of downtown. The bright, sunny first level of the main house features a large, open great room…

This brand-new (2025) guesthouse in Makonikey offers the perfect balance of style, comfort, and Vineyard charm. Designed with clean, contemporary lines, the home features an open-plan living and dining area with a chef’s kitchen and oversized island for gathering. Large windows bring in natural light, while sliding doors connect seamlessly to outdoor living spaces. The home includes two bedrooms with a shared bath, plus an outdoor shower for a true Vineyard summer…

Welcome to 11 Ocean View Farm Road, a thoughtfully designed contemporary retreat set in the heart of Chilmark, where sweeping ocean and hillside views, abundant natural light, and peaceful surroundings define the experience. Positioned on more than three acres, this home offers privacy, space, and a relaxed elegance that captures the essence of Martha’s Vineyard’s most scenic town. Designed to bring the outdoors in, the home features an open-concept main living area…

Effortless Vineyard living begins the moment you arrive. Perfectly positioned along the free VTA bus line, this newly built compound makes exploring the island simple! Step outside and ride straight into Vineyard Haven, Oak Bluffs, or Edgartown without ever moving your car.

Experience the effortless beauty of Chappaquiddick from this completely renovated top-to-bottom coastal farmhouse cottage overlooking the sweeping waters at Katama Bay. Thoughtfully reimagined with all-new furnishings, elevated finishes, and a light, airy design aesthetic, this retreat blends timeless Vineyard charm with modern comfort for a truly special island escape. The open-concept living, dining, and kitchen area is the heart of the home, inviting both relaxation and gathering. Expansive sliders open directly to…

(To book this property, please scroll down to the calendar. Available weeks are clearly listed. This home has a Friday-Friday turnover from July 31st to August 7th & a Sunday-Sunday turnover August 30th to September 6th, so online bookings must begin and end on its turnover day. A minimum stay of 7 nights is required. Questions can be directed to Ashley Killian, Ashley@portfoliopropertiesmv.com)

Welcome to Midland Haven, your ideal base for an unforgettable Vineyard stay. Nestled on a quiet street just a few blocks from downtown Vineyard Haven, this expansive two-level house offers comfortable, flexible living for families, multi-generational groups, or guests who value shared space and privacy. The Space • Upper Level Living (Main House) • 4 spacious bedrooms (including a master suite with its own full bath) in the main house • Additional full…

Step into this breathtaking Hutker-designed post-and-beam masterpiece overlooking the shimmering waters of Sengekontacket Pond. Nestled on Brush Island Lane in Oak Bluffs, this custom-built residence offers a rare combination of architectural sophistication, coastal tranquility, and private shoreline access — complete with a small, sandy beach for launching kayaks or simply soaking in the island sun. With approximately 3,600 square feet of inspired living space, this home balances soaring exposed-beam ceilings, walls of…

Discover one of the most magical waterfront experiences on Martha’s Vineyard at "The Westlake House", a unique three-level Vineyard-style cottage perched atop a 25-foot bluff overlooking the shimmering waters of Lagoon Pond and Nantucket Sound. With panoramic views, direct beach access, and postcard-perfect sunsets, this home captures everything you dream of in an island vacation. Follow the private wooded path down to over 110 feet of your own sandy shoreline—calm, clean, and…

Discover a truly special Vineyard escape at 80 Bellevue Avenue, a custom-built 3+ bedroom home offering sweeping water views of Lagoon Pond and a uniquely private setting surrounded by 15 acres of conservation land. This peaceful retreat places you close to Vineyard Haven’s amenities while giving you the tranquility and space of a nature-focused getaway. The main level features a full kitchen and bar area with direct access to an oversized garden…