Homes For Rent

(To book this property, Available weeks are clearly listed. A minimum stay of 7 nights is required. Questions can be directed to Ashley Killian, Ashley@portfoliopropertiesmv.com) Private Guest House with Its Own Driveway – Brand New & Fully Detached This private two-bedroom apartment offers a comfortable, fully independent stay with complete privacy. The space features two bedrooms, a full bathroom with a shower/tub combination, and in-unit washer and dryer for added convenience. The…

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…

(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. Questions can be directed to Ashley Killian, Ashley@portfoliopropertiesmv.com)

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 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…

Welcome to 4 Essex Court, an adorable contemporary Cape tucked into a quiet Edgartown neighborhood that’s perfect for anyone looking for a relaxed island escape. With cathedral ceilings, comfortable furnishings, air conditioning, and an open layout, this home delivers the classic Vineyard vacation experience with all the modern conveniences. The first floor features an open kitchen, dining, and living area—bright, inviting, and ideal for gathering after a day at the beach. Sliding…

Welcome to your Martha’s Vineyard escape in the desirable Meadow View Farms neighborhood of Oak Bluffs. Surrounded by natural beauty and designed for comfort, this inviting four-bedroom, three-bath home offers over 3,000 square feet of thoughtfully designed living space for families and friends to gather. The main living area is bright and airy, with soaring ceilings, abundant natural light, and an open-concept layout that creates a warm, welcoming atmosphere. The spacious kitchen…

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…

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…

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.

Located in the heart of Katama, Edgartown, this stunning 3-bedroom, 4.5-bath retreat captures the essence of Martha’s Vineyard living — bright, open, and effortlessly elegant. Bathed in natural light, the home offers a seamless blend of luxury and comfort, featuring spacious living areas, a chef’s kitchen, and expansive decks perfect for morning coffee or sunset cocktails. Just minutes from South Beach and a quick bike ride or drive to Downtown Edgartown’s shops,…

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…

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…

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,…

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. Step inside to a bright and inviting interior with recently refreshed furnishings, an open and easy layout, and…

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…

Welcome to 7 Sparrow Lane, a beautifully designed contemporary retreat located in the desirable Dodger’s Hole neighborhood of Edgartown. Built with comfort, style, and easy vacation living in mind, this home offers bright interiors, refined finishes, and a layout perfectly suited for families or friends gathering on Martha’s Vineyard. The main living space is an impressive open living–dining–kitchen great room with vaulted ceilings and a striking beach stone fireplace, creating a warm…

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…

Charming 2 Bedroom Cottage in Vineyard Haven Close to Main Street

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…

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. Questions can be directed to Ashley Killian, Ashley@portfoliopropertiesmv.com