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…

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…

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 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…

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…

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…

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.

Welcome to Crocker Avenue in Vineyard Haven, a striking 18th-century waterfront home that brings old-world New England charm to life—now available as a vacation retreat in the heart of Vineyard Haven. This elegant residence, perched directly on the harbor with its own private sandy beach, offers sweeping water views and easy access to the picturesque town center. Step into a gracious living room with original wide pine floors, antique furnishings, and a…

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…

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…

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,…

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 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 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…

Effortless Vineyard living begins the moment you arrive. Perfectly positioned along the free VTA bus line, this newly built compound makes exploring the island simple! Step outside and ride straight into Vineyard Haven, Oak Bluffs, or Edgartown without ever moving your car.

Rental Property Description

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…

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…

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. This property does not provide linens. Questions can be directed to Ashley Killian, Ashley@portfoliopropertiesmv.com

MORE 2027 AVAILIBILITY COMING SOON! Welcome to your ultimate Martha’s Vineyard retreat. Perfectly situated where Katama meets historic Edgartown (only 0.9 miles away!), this striking 5-bedroom, 3.5-bathroom modern farmhouse sits on several pristine, private acres—offering the rare combination of peaceful seclusion, expansive lawn space, and easy access to both South Beach (3.0 miles) and downtown Edgartown. The Space Architectural Grandeur & Living Step through the front entrance into a breathtaking double-height foyer…

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.…