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 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 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…

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 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…

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…

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, 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. 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)

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…

(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 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…

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…

(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…

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,…

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…

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…

Available weeks are listed for your convenience. Turnover days may adjust depending on the calendar, and minimum night stays may apply during high-demand weeks. I’m happy to answer any questions or help with booking — please reach out to Ashley Killian at Ashley@portfoliopropertiesmv.com. Wake up to serene views and easy island living at this bright and welcoming Oak Bluffs retreat. Nestled near local beaches, charming town spots, and scenic bike paths, this…