Homes For Rent

(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.)

Settle into an easy island rhythm at this comfortable three-bedroom, two-bath Edgartown home, featuring an updated kitchen and plenty of room to relax.

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…

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 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…

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 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…

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…

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…

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,…

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.

Tucked into the heart of Chappaquiddick, this charming cottage offers a cozy queen loft, two twin beds, and an inviting deck with a grill and bistro lighting—all near the Royal and Ancient Golf Course.

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…

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…