Homes For Rent

(To book this property, please scroll down to the calendar. 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)

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…

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, 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)

(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)

(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…

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…

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.…

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…

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…

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…

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…

Set against one of Katama’s most picturesque backdrops, 81-A Herring Creek Road is a thoughtfully updated guest house offering style, comfort, and sweeping pastoral views across 50 acres of protected conservation land with open fields, wildflowers, and a working horse barn. With its Western-inspired character and fresh, modern upgrades, this home is both welcoming and unique. Inside, the space feels bright and airy, highlighted by a brand-new kitchen and newly renovated bathrooms…

Welcome to this serene Martha’s Vineyard escape set along a winding dirt road in the highly sought-after Lower Makonikey area. Surrounded by 3 peaceful acres of natural landscape, this thoughtfully designed four-bedroom, four-bath home offers privacy, comfort (central A/C), and access to one of the island’s most treasured private association beaches. From the moment you arrive, the home invites you to slow down and settle into island life. Mature trees, open sky,…

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 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)

Welcome to 44 North Road, a gracious and beautifully renovated Mill Pond-front farmhouse in the heart of West Tisbury, offering the perfect blend of Vineyard charm, privacy, and natural beauty. Set on approximately five acres and perched along the edge of picturesque Mill Pond, this special property offers a peaceful setting where guests can kayak, swim, and unwind right from the backyard. Classic New England farmhouse character meets thoughtful modern comfort throughout…

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 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…

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…

(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)