Luxury Homes
Where the island shows it's finest self
Martha's Vineyard has long drawn those who understand that true luxury is not loudness — it is space, light, and the rare feeling that everything has been considered. This is an island of weathered shingles and sweeping ocean views, of long porches and unhurried evenings, of a quiet that the right home can offer in abundance. Our collection of luxury rentals captures exactly that: properties where the architecture, the setting, and the details conspire to make every moment feel effortless.
These are homes that go well beyond a place to sleep. Think chef's kitchens, private pools, sprawling decks and patios, water views and interiors furnished with the kind of care that makes you want to stay in as much as go out. Whether you are gathering family, hosting close friends, or simply treating yourself to the holiday you have been promising for years, these homes meet you at exactly that moment.
Each property in this collection has been chosen for its exceptional quality, distinctive character, and ability to make a stay feel genuinely memorable — not merely comfortable. From refined retreats in Oak Bluffs to grand shingle-style compounds in Edgartown, these are homes with a point of view. They ask nothing of you except to arrive, settle in, and let the island do what it does best.
Browse the collection below — your finest Vineyard summer begins here.
54 properties available
Stunning Chilmark contemporary home with a pool is situated high up from the water with fabulous views of the North Shore. There are numerous paths to wander in the woods. Privacy, privacy, privacy offered on twenty two acres. Great space in the main house with five bedrooms on the main level and overflow off of the finished family room downstairs.
Chilmark 2060
Stunning Chilmark contemporary home with a pool is situated high up from the water with fabulous views of the North Shore. There are numerous paths to... Read More
Stunning Chilmark contemporary home with a pool is situated high up from the water with fabulous views of the North Shore. There are numerous paths to... Read More
Nestled on the tranquil bay side of Katama, this remarkable rental property stands as a true gem in the coastal landscape. A single-level architectural marvel bathes its interiors in an abundance of natural light, creating an inviting and spacious atmosphere. With two bedrooms boasting its own private bath, and two additional bunk rooms sharing the
Edgartown Katama 7028
Nestled on the tranquil bay side of Katama, this remarkable rental property stands as a true gem in the coastal landscape. A single-level architectura... Read More
Nestled on the tranquil bay side of Katama, this remarkable rental property stands as a true gem in the coastal landscape. A single-level architectura... Read More
A stunning home on a stunning property. As you enter the home and look through the floor to ceiling windows to the pool and the Edgartown Harbor beyond, you will feel the magnificence of this home. The kitchen, living room and dining area flow together seamlessly while you are able to see the outside from every angle. There is a primary suite on ea
Edgartown Katama 7210
A stunning home on a stunning property. As you enter the home and look through the floor to ceiling windows to the pool and the Edgartown Harbor beyon... Read More
A stunning home on a stunning property. As you enter the home and look through the floor to ceiling windows to the pool and the Edgartown Harbor beyon... Read More
In a word? Magnificent. Located in the private community of Bayside, nestled along the waterfront of Katama Bay, the sense of tranquility at this newly built, beautiful home is truly captivating - the modern design includes luxe finishes while simultaneously encompassing the elements of the surrounding landscape, creating a space which is both rela
Edgartown Katama 7196
In a word? Magnificent. Located in the private community of Bayside, nestled along the waterfront of Katama Bay, the sense of tranquility at this newl... Read More
In a word? Magnificent. Located in the private community of Bayside, nestled along the waterfront of Katama Bay, the sense of tranquility at this newl... Read More
Sited on 9-acres overlooking Edgartown Great Pond, this stunning home is nothing shy of a masterpiece. Meticulously thought out in design, every detail is attended to, ensuring an unparalleled living AND vacationing experience. A luxuriously equipped interior in the softest of pallets with seven bedrooms, including five en-suite, multiple living ar
Edgartown 7805
Sited on 9-acres overlooking Edgartown Great Pond, this stunning home is nothing shy of a masterpiece. Meticulously thought out in design, every detai... Read More
Sited on 9-acres overlooking Edgartown Great Pond, this stunning home is nothing shy of a masterpiece. Meticulously thought out in design, every detai... Read More
A contemporary home featuring mid-century modern decor creates a truly unique atmosphere. The custom details, including tailor-made headboards and a stunning 12 x 4-foot mahogany dining table, enhance the property's natural tranquility. The gourmet kitchen is equipped with dual ovens, a downdraft Zline stove, and a wine cooler, adding a touch of gl
Edgartown 7731
A contemporary home featuring mid-century modern decor creates a truly unique atmosphere. The custom details, including tailor-made headboards and a s... Read More
A contemporary home featuring mid-century modern decor creates a truly unique atmosphere. The custom details, including tailor-made headboards and a s... Read More
Steeped in history, exuding luxury. The traditional whaling captain's home has been renovated to include seven bedrooms and seven and a half bathrooms over three buildings. Starting in the main house, you enter through perfectly replicated antique doors. On this level you will find a lovely sitting area that closes off for privacy and the first of
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Edgartown Downtown 25
Steeped in history, exuding luxury. The traditional whaling captain's home has been renovated to include seven bedrooms and seven and a half bathrooms... Read More
Steeped in history, exuding luxury. The traditional whaling captain's home has been renovated to include seven bedrooms and seven and a half bathrooms... Read More
Nestled in a serene and secluded setting on the shore of Watcha Pond, this stunning 5-bedroom, 4.5-bathroom home spans 4,000 sq. ft. of luxurious living space. The open concept kitchen, dining, and living area create a spacious, airy atmosphere perfect for both everyday lounging and entertaining guests. The expansive one story layout features large
West Tisbury 100051
Nestled in a serene and secluded setting on the shore of Watcha Pond, this stunning 5-bedroom, 4.5-bathroom home spans 4,000 sq. ft. of luxurious livi... Read More
Nestled in a serene and secluded setting on the shore of Watcha Pond, this stunning 5-bedroom, 4.5-bathroom home spans 4,000 sq. ft. of luxurious livi... Read More
This stunning new 4-bedroom home offers the perfect blend of elegance, comfort, and convenience. Nestled in a desirable location, you'll find yourself just a short stroll away from downtown Edgartown, where you can enjoy the vibrant atmosphere, exquisite dining options, and boutique shopping. Inside, you will be captivated by the sun-soaked interio
Edgartown Downtown 18
This stunning new 4-bedroom home offers the perfect blend of elegance, comfort, and convenience. Nestled in a desirable location, you'll find yourself... Read More
This stunning new 4-bedroom home offers the perfect blend of elegance, comfort, and convenience. Nestled in a desirable location, you'll find yourself... Read More
Take a three minute ferry ride from the village of Edgartown to arrive at this stunning Four Bedroom waterfront home located on Chappaquiddick Island. Plenty of space for entertaining with a large open dining and living area, opening out onto the deck. Recently updated, the house offers up-scale amenities and Central AC for those warm summer nights
Edgartown Chappaquiddick 418
Take a three minute ferry ride from the village of Edgartown to arrive at this stunning Four Bedroom waterfront home located on Chappaquiddick Island.... Read More
Take a three minute ferry ride from the village of Edgartown to arrive at this stunning Four Bedroom waterfront home located on Chappaquiddick Island.... Read More
Stunning and immaculate 4500 square foot, 5 bedroom, custom Field Club home is waiting for your enjoyment. Inside you will find an open floor plan that extends the full length of the home. A large fully equipped chefs kitchen with a working island with access to ample seating, which spills to either indoor or outdoor dining just steps away. The f
Edgartown Katama 601
Stunning and immaculate 4500 square foot, 5 bedroom, custom Field Club home is waiting for your enjoyment. Inside you will find an open floor plan t... Read More
Stunning and immaculate 4500 square foot, 5 bedroom, custom Field Club home is waiting for your enjoyment. Inside you will find an open floor plan t... Read More
Welcome to your Martha's Vineyard retreat in Edgartown! This stunning home, a testament to modern luxury, boasts new construction and is beautifully furnished throughout. Spacious and tastefully decorated living space, where the open-concept layout seamlessly connects the living room, dining area, and fully equipped kitchen, making it perfect for e
Edgartown Downtown 11
Welcome to your Martha's Vineyard retreat in Edgartown! This stunning home, a testament to modern luxury, boasts new construction and is beautifully f... Read More
Welcome to your Martha's Vineyard retreat in Edgartown! This stunning home, a testament to modern luxury, boasts new construction and is beautifully f... Read More
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