Homes For Rent

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…

(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)

Beautifully blending modern coastal design with the relaxed lifestyle that makes Martha’s Vineyard so special, this exceptional Edgartown home offers the perfect setting for families and friends seeking an unforgettable island getaway. Filled with natural light and thoughtfully designed throughout, the home welcomes guests into an open-concept living space where the kitchen, dining area, living room, screened porch, and expansive deck all flow seamlessly together. Whether preparing a casual breakfast before heading…

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…

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…

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…

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 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 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…

Perched on the top floor of the Seaview Condominiums, Unit #304 at 2 Pennacook Avenue delivers one of Oak Bluffs’ most captivating vantage points. With sweeping ocean views from nearly every room, dramatic vaulted ceilings, and a private balcony overlooking the water, this beautifully furnished two-bedroom, two-bath residence offers a refined and memorable Martha’s Vineyard vacation experience. The interior is contemporary and thoughtfully styled, blending comfort with clean, modern design. The open…

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…

Tucked into the rolling landscape of Chilmark, 50 Putnam Road is a gracious and spacious retreat offering the perfect balance of privacy, comfort, and classic Martha’s Vineyard serenity. With over 3,600 square feet of living space, five bedrooms, and five and a half baths, this home is ideally suited for families or groups seeking a relaxed yet elevated island getaway. The interior is thoughtfully designed for both gathering and retreat. Generous common…

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…

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.

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…

Set against a backdrop of protected farmland and open Vineyard skies, Katama Landing is a rare architectural offering that seamlessly blends modern design, luxury amenities, and the natural beauty of Martha’s Vineyard. Thoughtfully designed with clean lines, weathered cedar shingles, dramatic glass walls, and warm walnut flooring, the home creates a sophisticated yet welcoming atmosphere from the moment you arrive. Every detail has been carefully considered, resulting in a residence that feels…

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 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…

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…

Beautifully modern, architectural farmhouse, featuring open living spaces with soaring cathedral ceilings and glass walls that open to the patio and yard areas. This home offers privacy and peace, just a mile from Lambert’s Cove Beach. The property backs up to protected MV Landbank acreage and is just an 8-minute walk to Ice House Pond, where guests can enjoy a freshwater swim. The house also has a stunning, heated pool, steps from…

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,…