• 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
  • Pets allowed
From $3,500 / week

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…

  • 4 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 8
  • No pets
From $7,000 / week

Tucked in the heart of West Tisbury, this inviting Vineyard retreat blends the comfort of home with the charm of island living. Thoughtfully renovated and surrounded by peaceful greenery, this home offers space to relax, gather, and create summer memories. The bright, open interior features a warm and welcoming living area, an updated kitchen stocked with all the essentials, and an easy flow between spaces for dining and conversation. With four comfortable…

  • 5 Bedrooms
  • 3.5 Bathrooms
  • Sleeps 9
  • No pets
From $12,500 / week

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…

  • 4 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
  • No pets
From $5,000 / week

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,…

  • 2 Bedrooms
  • 1 Bathroom
  • Sleeps 4
  • No pets
From $4,000 / week

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…

  • 4 Bedrooms
  • 2 Bathrooms
  • Sleeps 9
  • No pets
From $3,339 / week

(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)

  • 3 Bedrooms
  • 4.5 Bathrooms
  • Sleeps 10
  • No pets
From $5,500 / week

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,…