Homes For Rent

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, 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)

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 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,…

(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 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…

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,…

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.…

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 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…

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…

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…

Updated for bookings in 2026!! SO CLOSE TO TOWN! If you are searching for a place that accommodates your group while staying close to Oak Bluffs town center, then search no further. Your guests will have a choice of two first floor bedrooms, and 3 upstairs bedrooms including a master suite that has its own private seating area. This property offers 3 full bathrooms and one outdoor shower. The kitchen offers high…

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…

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…

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…

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…

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,…

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,…