Homes For Rent

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 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,…

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…

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 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…

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,…

(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)

With four bedrooms and four en-suite bathrooms plus a half bath, the home is particularly well suited to families, couples traveling together or a multigenerational Vineyard vacation.

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 Vineyard Haven home away from home. This newly renovated six-bedroom property combines modern comfort with classic Martha's Vineyard charm, all within walking distance of downtown Vineyard Haven, public beaches, local restaurants, coffee shops, boutiques, and the ferry terminal. Thoughtfully designed for multi-generational families and group gatherings, the home comfortably accommodates a variety of sleeping arrangements with two king bedrooms, one queen bedroom, two full beds, three twin beds, and…

Discover the quiet charm of Chappaquiddick from this spacious 3,600-square-foot Island retreat, ideally situated approximately one block from the beach and offering beautiful water views. Surrounded by the natural beauty that makes Chappaquiddick one of Martha's Vineyard's most treasured destinations, this welcoming home is designed for memorable family vacations and peaceful coastal escapes. Inside, generous living spaces provide plenty of room to gather, unwind, and enjoy time together after days spent exploring…

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.

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…

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…

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…

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.

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,…

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…

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…

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…

(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…