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
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
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
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
This stunning walk to Edgartown home offers the best of both worlds: a serene private setting at the end of the cul-de-sac and prime access to Edgartown village. Just steps from a playground, pickleball courts, and a park, this home is designed for outdoor living! The spacious 600 square foot front porch, with its rocking chairs, swing and dining t
Edgartown Downtown 150
This stunning walk to Edgartown home offers the best of both worlds: a serene private setting at the end of the cul-de-sac and prime access to Edgarto... Read More
This stunning walk to Edgartown home offers the best of both worlds: a serene private setting at the end of the cul-de-sac and prime access to Edgarto... 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
Striking Edgartown home waiting for you to create your lasting vacation memories! This superior location suits every family member. You are a block away from your morning coffee, or if you are feeling more ambitious you are a bit under a mile to Main Street in Edgartown. Hop on a bike and pedal to South Beach in a little under three miles with bike
Edgartown Katama 552
Striking Edgartown home waiting for you to create your lasting vacation memories! This superior location suits every family member. You are a block aw... Read More
Striking Edgartown home waiting for you to create your lasting vacation memories! This superior location suits every family member. You are a block aw... Read More
Discover the ultimate 5-bedroom retreat, where luxury and relaxation converge to redefine your vacation experience. This top-of-the-line, two-story home features central air, an inviting swimming pool, a sauna, cold plunge, and ocean views. Enjoy the spacious elegance and bright living spaces in the main house, featuring an en suite bedroom conven
Edgartown Chappaquiddick 300
Discover the ultimate 5-bedroom retreat, where luxury and relaxation converge to redefine your vacation experience. This top-of-the-line, two-story h... Read More
Discover the ultimate 5-bedroom retreat, where luxury and relaxation converge to redefine your vacation experience. This top-of-the-line, two-story h... Read More
Designed by renowned architect Patrick Ahearn, this house offers a contemporary interpretation of a Martha's Vineyard Cape. Evoking the grandeur of an equestrian estate, this six-bedroom, nine-bath home is perched on a hill, overlooking a pond and situated on nearly four acres in the Preserve. The impeccably designed interiors create a sense of pla
Oak Bluffs 8168
Designed by renowned architect Patrick Ahearn, this house offers a contemporary interpretation of a Martha's Vineyard Cape. Evoking the grandeur of an... Read More
Designed by renowned architect Patrick Ahearn, this house offers a contemporary interpretation of a Martha's Vineyard Cape. Evoking the grandeur of an... Read More
A beautiful home tucked just off of Fuller Street in downtown Edgartown with a show-stopping decor from Oomph Designs, this four-bedroom home includes a sprawling lawn and swimming pool, three bedrooms in the main house plus an additional bedroom and ensuite bath over the garage, all a short distance from Fuller Street Beach and downtown Edgartown.
Edgartown Downtown 143
A beautiful home tucked just off of Fuller Street in downtown Edgartown with a show-stopping decor from Oomph Designs, this four-bedroom home includes... Read More
A beautiful home tucked just off of Fuller Street in downtown Edgartown with a show-stopping decor from Oomph Designs, this four-bedroom home includes... Read More
A stunning home that exudes sophistication and a keen eye for design, this contemporary 5 bedroom, 4 bathroom home encompasses all of your vacations wants AND needs. The reverse floorplan has 3 bedrooms, two baths and a beautiful living space on the first floor, along with expansive windows and doors to beyond. The second floor unfolds in an open c
Edgartown Katama 5022
A stunning home that exudes sophistication and a keen eye for design, this contemporary 5 bedroom, 4 bathroom home encompasses all of your vacations w... Read More
A stunning home that exudes sophistication and a keen eye for design, this contemporary 5 bedroom, 4 bathroom home encompasses all of your vacations w... Read More
Escape to the epitome of luxury at this exquisite 4-bedroom, 3.5-bath vacation home in the heart of Katama. Enjoy the elegance of high-end furnishings and the generous space of this sophisticated home while enjoying peeks of Edgartown Great Pond. The open concept design features a gorgeous chef's kitchen, a spacious family room, and a generous dini
Edgartown Katama 521
Escape to the epitome of luxury at this exquisite 4-bedroom, 3.5-bath vacation home in the heart of Katama. Enjoy the elegance of high-end furnishings... Read More
Escape to the epitome of luxury at this exquisite 4-bedroom, 3.5-bath vacation home in the heart of Katama. Enjoy the elegance of high-end furnishings... Read More
This Martha's Vineyard property is a great vacation home to experience the beautiful island setting in the town of Aquinnah. New four bedroom custom home which overlooks the Vineyard Sound, offering breathtaking panoramic views to the Elizabeth Islands. With state of the art decor and interior furnishings, guests will enjoy environmentally sensiti
Aquinnah 2501
This Martha's Vineyard property is a great vacation home to experience the beautiful island setting in the town of Aquinnah. New four bedroom custom ... Read More
This Martha's Vineyard property is a great vacation home to experience the beautiful island setting in the town of Aquinnah. New four bedroom custom ... Read More
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