Homes For Rent

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 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 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…

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…

(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)

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.

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…

(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)

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…

(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)

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…

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…

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…

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 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…

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,…

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…

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…

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…

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 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…