Homes For Rent

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…

Welcome to Crocker Avenue in Vineyard Haven, a striking 18th-century waterfront home that brings old-world New England charm to life—now available as a vacation retreat in the heart of Vineyard Haven. This elegant residence, perched directly on the harbor with its own private sandy beach, offers sweeping water views and easy access to the picturesque town center. Step into a gracious living room with original wide pine floors, antique furnishings, and a…

Welcome to 3 Cottonwood Lane, a warm and welcoming Colonial-style home just outside the center of Edgartown, offering comfort, charm, and a relaxed setting for your Martha’s Vineyard getaway. With its classic design, thoughtful layout, and easy indoor–outdoor living, this home is ideal for families or friends looking for a casual and convenient island retreat. The home is nicely landscaped and includes a small grassy backyard, perfect for outdoor games, morning coffee,…

Whether you're exploring Circuit Avenue in Oak Bluffs, strolling Main Street in Vineyard Haven, or simply enjoying a quiet evening by the water, this cottage offers an authentic Martha's Vineyard experience in an unbeatable location.Classic waterfront cottage on Beach Road between Oak Bluffs and Vineyard Haven featuring two bedrooms, private shoreline, walking access to two public beaches, outdoor decks, and one of the island's most sought-after locations.

Welcome to 40 Orchard Road, an exceptional West Tisbury retreat offering the rare combination of privacy, space, and classic Martha’s Vineyard charm. Set on 4.5 lush acres of rolling woodland and open lawn, this peaceful escape is ideal for families or friends seeking room to spread out while remaining conveniently close to the island’s beloved beaches, village centers, and dining spots. This property features a beautifully appointed main residence along with a…

Escape to Katama and experience Martha’s Vineyard at its best in this bright, contemporary coastal home overlooking beautiful Katama Bay. Perfectly positioned between South Beach and Edgartown Village, this stylish retreat delivers water views, effortless indoor-outdoor living, and the relaxed luxury that defines a true Vineyard vacation. Step inside to a sun-drenched great room with vaulted ceilings, exposed beams, and an entire wall of glass that frames the blue of the bay.…

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.

(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)

Freshly Renovated Vineyard Haven Cottage | NEW Vacation Rental Be among the first guests to enjoy this charming Vineyard Haven retreat, offered as a vacation rental for the very first time. Thoughtfully updated while maintaining its classic Martha’s Vineyard character, this inviting two-bedroom, two-bath home offers the perfect setting for families, couples, or friends seeking a relaxing Island getaway. Bright interiors, comfortable furnishings, and peaceful outdoor spaces create an easygoing atmosphere where…

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…

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…

Tucked in the heart of West Tisbury, this inviting Vineyard retreat blends the comfort of home with the charm of island living. Thoughtfully renovated and surrounded by peaceful greenery, this home offers space to relax, gather, and create summer memories. The bright, open interior features a warm and welcoming living area, an updated kitchen stocked with all the essentials, and an easy flow between spaces for dining and conversation. With four comfortable…

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…

Nestled in a quiet cul-de-sac just moments from the heart of Vineyard Haven, this luminous three-bedroom, 2½ bath home offers the perfect balance of peaceful privacy and convenience. You won’t find many vacation rentals that marry roomy indoor-outdoor living with such proximity to downtown, the harbor, and the ferry. From your front door, the town’s vibrant Main Street is just a short distance away — picture morning coffee from a local café,…

(To book this property, Available weeks are clearly listed. This home has a Friday-Friday turnover, so online bookings must begin and end on a Friday. A minimum stay of 7 nights is required.)

Set in the heart of Katama, this gracious farmhouse at 81 Herring Creek Road offers a rare combination of space, scenery, and relaxed Vineyard living. Situated on more than four acres, the home enjoys sweeping views across 50 acres of protected conservation fields, where wildflowers, open pasture, and a working horse barn create a serene and ever-changing backdrop throughout the season. Designed for comfort and connection, the home provides generous indoor and…

Welcome to 64 Saddle Club Road, a privately custom-built Edgartown retreat designed for comfort, relaxation, and effortless Vineyard living. Located in a quiet, secluded neighborhood yet just a 10-minute ride to downtown Edgartown, this home offers the best of both worlds—peaceful privacy and unbeatable convenience. Set on over half an acre of beautifully landscaped grounds, the property has been meticulously maintained and thoughtfully upgraded to meet the needs of today’s vacationers. With…

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…

This lovely yellow cottage is well appointed and close to town and a quick walk to Fuller Beach, ride the bike path out to South Beach or take a stroll into town to walk along the docks. It is beautifully furnished including a fireplace in the living room. Updated kitchen and bathrooms. This Cottage can sleep up to 10 and the guest cottage can accommodate another four.

What Makes This Place Special Close to everything — The ferry landing is only a short distance away, putting you minutes from arriving or departing. Half a block from your front door, you’ll find the shops, eateries, and ice cream stands of Main Street. When the mood strikes, you’ll be at the Harbor in moments, watching boats come and go, or enjoying waterfront sunsets. Historic charm meets modern comfort — Beautifully appointed…

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…