Martha’s Vineyard Vacation Rentals

Perched on the top floor of the Seaview Condominiums, Unit #304 at 2 Pennacook Avenue delivers one of Oak Bluffs’ most captivating vantage points. With sweeping ocean views from nearly every room, dramatic vaulted ceilings, and a private balcony overlooking the water, this beautifully furnished two-bedroom, two-bath residence offers a refined and memorable Martha’s Vineyard vacation experience.

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 and dining areas flow seamlessly into the living room, making entertaining easy after a day at the beach or exploring the island.

(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)

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 ideal for kayaking, paddleboarding, canoeing, and swimming. Gentle breezes make this a spectacular spot for sailing or windsurfing, and you’ll love watching the ferry glide in and out of Vineyard Haven across the bay.

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 glass, and warm natural materials to create an atmosphere that feels both grand and grounded in its surroundings.

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.

Welcome to Seaview Condominium #203 at 2 Pennacook Avenue, a beautifully appointed coastal retreat offering elevated views and relaxed comfort in the heart of Oak Bluffs.

Wake up overlooking Vineyard Sound at this classic Beach Road cottage, ideally positioned between Oak Bluffs and Vineyard Haven. Designed for a simple, relaxed Vineyard stay, the home offers a private rocky shoreline, a waterfront sitting porch, a separate sun deck and convenient access to nearby beaches and both harbor towns. Inside, the cottage retains its nostalgic island character while offering refreshed flooring, fresh paint and comfortable accommodations for up to four guests. Spend the morning by the water, explore the Island during the day and return for ocean breezes and sunset views from the deck.

Welcome to Arrowsmith Cottage – a clean, comfortable and casually stylish home base for a carefree Martha's Vineyard vacation, any time of year.