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.


Properties Available 55 properties available
Chilmark waterfront rental home with a dock located on Quitsa Pond with views across Quitsa and Menemsha ponds out to the Elizabeth Islands. This Martha's Vineyard rental property offers dock, mooring along with access to small beach area just down the path on Clam Point Cove. Fully renovated in 2022 with stunning views from almost every room. Enj
$10,000.00 - $19,000.00 / per week + taxes and fees
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps sleeps 8
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Chilmark 2021
Chilmark waterfront rental home with a dock located on Quitsa Pond with views across Quitsa and Menemsha ponds out to the Elizabeth Islands. This Mart... Read More
June 2027
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13 14 15 16 17 18 $15,000 19
20 21 22 23 24 25 $16,000 26
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25 26 27 28 29 30 $19,000 31
August 2027
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8 9 10 11 12 13 $19,000 14
15 16 17 18 19 20 $19,000 21
22 23 24 25 26 27 $19,000 28
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Edgartown 7747
... Read More
June 2027
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    1 2 3 4 $20,000 5
6 7 8 9 10 11 $20,000 12
13 14 15 16 17 18 $20,000 19
20 21 22 23 24 25 $30,000 26
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        1 2 $30,000 3
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25 26 27 28 29 30 $32,000 31
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1 2 3 4 5 6 $32,000 7
8 9 10 11 12 13 $32,000 14
15 16 17 18 19 20 $32,000 21
22 23 24 25 26 27 $20,000 28
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This modern contemporary home provides the ideal setting for your Martha's Vineyard vacation. The clean, sleek lines throughout enhance the relaxed living atmosphere. The open kitchen, dining, and living space make entertaining comfortable, and a second sunken living area opens to a fabulous deck overlooking beautiful landscaping and gardens. Each
$25,000.00 - $25,500.00 / per week + taxes and fees
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps sleeps 8
Pet Friendly Pets Considered
Not Pet Friendly No Events/Gatherings
Edgartown Katama 514
This modern contemporary home provides the ideal setting for your Martha's Vineyard vacation. The clean, sleek lines throughout enhance the relaxed li... Read More
June 2027
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    1 2 3 4 $25,500 5
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13 14 15 16 17 18 $25,500 19
20 21 22 23 24 25 $25,500 26
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11 12 13 14 15 16 $25,500 17
18 19 20 21 22 23 $25,500 24
25 26 27 28 29 30 $25,500 31
August 2027
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8 9 10 11 12 13 $25,500 14
15 16 17 18 19 20 $25,500 21
22 23 24 25 26 27 $25,500 28
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Picture yourself enjoying every luxurious detail of this gorgeous 4 bedroom home located approximately 1 mile from Downtown Edgartown. The first floor offers spacious living and dining space and a stunning eat in kitchen. The primary bedroom is truly an oasis with a soaking tub in the en suite bathroom and direct access to the pool. The remaining t
$11,500.00 - $26,000.00 / per week + taxes and fees
Beds 4 beds
Baths 5 Full, 1 Half Bath
Sleeps sleeps 8
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Katama 722
Picture yourself enjoying every luxurious detail of this gorgeous 4 bedroom home located approximately 1 mile from Downtown Edgartown. The first floor... Read More
June 2027
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    1 2 3 4 $13,000 5
6 7 8 9 10 11 $13,000 12
13 14 15 16 17 18 $15,000 19
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4 5 6 7 8 9 $22,000 10
11 12 13 14 15 16 $22,000 17
18 19 20 21 22 23 $22,000 24
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August 2027
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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
$10,000.00 - $30,000.00 / per week + taxes and fees
Beds 5 beds
Baths 4 Full, 1 Half Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
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
June 2027
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    1 2 3 4 $15,000 5
6 7 8 9 10 11 $15,000 12
13 14 15 16 17 18 $20,000 19
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        1 2 $25,000 3
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1 2 3 4 5 6 $30,000 7
8 9 10 11 12 13 $30,000 14
15 16 17 18 19 20 $30,000 21
22 23 24 25 26 27 $25,000 28
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Stunning views over Eel Pond are perhaps the piece de resistance at this stunning in-town compound - bordered by the wildflowers of conservation land - the trails of Sheriff's Meadow are just one of the many afternoon adventures. Standing on the second floor deck and looking over the sprawling landscape, you truly feel on top of the world. The main
$40,000.00 - $50,212.50 / per week + taxes and fees
Beds 6 beds
Baths 7 Full, 1 Half Bath
Sleeps sleeps 12
Pet Friendly Pets Considered
Not Pet Friendly No Events/Gatherings
Edgartown Downtown 71
Stunning views over Eel Pond are perhaps the piece de resistance at this stunning in-town compound - bordered by the wildflowers of conservation land ... Read More
June 2027
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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
$35,000.00 / per week + taxes and fees
Beds 5 beds
Baths 7 Full Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
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
June 2027
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Unparalleled views overlooking Moshup beach, this stunning home has some of the most spectacular views available on the Vineyard. High end amenities throughout, with exquisite detail in every sense. The bedding, linens, and decor are all top of the line. Each bedroom is en suite, and each level has a family room with smart tv's. The multi level wra
$11,000.00 - $22,000.00 / per week + taxes and fees
Beds 4 beds
Baths 4 Full, 1 Half Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Aquinnah 2502
Unparalleled views overlooking Moshup beach, this stunning home has some of the most spectacular views available on the Vineyard. High end amenities t... Read More
June 2027
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    1 2 3 4 $11,000 5
6 7 8 9 10 11 $11,000 12
13 14 15 16 17 18 $16,500 19
20 21 22 23 24 25 $19,800 26
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        1 2 $19,800 3
4 5 6 7 8 9 $19,800 10
11 12 13 14 15 16 $22,000 17
18 19 20 21 22 23 $22,000 24
25 26 27 28 29 30 $22,000 31
August 2027
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1 2 3 4 5 6 $22,000 7
8 9 10 11 12 13 $22,000 14
15 16 17 18 19 20 $22,000 21
22 23 24 25 26 27 $21,057 28
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Upon entering the prestigious Field Club development, you will be graced by an exquisitely designed home with a wonderful eye for detail. It is furnished with the finest linens, bedding, furniture and plenty of comfy sofas throughout. The first floor offers a long open floor plan beginning with a chefs dream kitchen of black granite counter tops
$20,000.00 - $40,000.00 / per week + taxes and fees
Beds 5 beds
Baths 4 Full Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Katama 7182
Upon entering the prestigious Field Club development, you will be graced by an exquisitely designed home with a wonderful eye for detail. It is furni... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $25,000 5
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20 21 22 23 24 25 $40,000 26
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        1 2 $40,000 3
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18 19 20 21 22 23 $40,000 24
25 26 27 28 29 30 $40,000 31
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15 16 17 18 19 20 $40,000 21
22 23 24 25 26 27 $30,000 28
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Vacation bliss awaits in this newer four-bedroom home with a pool in Chilmark. Enjoy the quiet luxury of up-island in this sophisticated contemporary retreat. Lounge by the pool, dine outdoors, and sleep peacefully in one of the Thuma beds. The main floor offers open-concept living, dining and kitchen spaces with grand vaulted ceilings anchored by
Hot HOT 11
$15,000.00 - $20,000.00 / per week + taxes and fees
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps sleeps 8
Pet Friendly Pets Considered
Not Pet Friendly No Events/Gatherings
Chilmark 2001
Vacation bliss awaits in this newer four-bedroom home with a pool in Chilmark. Enjoy the quiet luxury of up-island in this sophisticated contemporary ... Read More
June 2027
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    1 2 3 4 $15,000 5
6 7 8 9 10 11 $15,000 12
13 14 15 16 17 18 $15,000 19
20 21 22 23 24 25 $20,000 26
27 28 29 30      
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4 5 6 7 8 9 $20,000 10
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8 9 10 11 12 13 $20,000 14
15 16 17 18 19 20 $18,000 21
22 23 24 25 26 27 $15,000 28
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No detail was overlooked in the design of this stunning five-bedroom home set on the hill. This home offers comfort and style and features rich countertops, stainless steel appliances, and an open floor plan that flows effortlessly between the kitchen, dining, and living areas. Three of the five bedrooms are en-suites, and the third-floor media and
Hot HOT 27
$20,000.00 - $40,000.00 / per week + taxes and fees
Beds 5 beds
Baths 5 Full, 1 Half Bath
Sleeps sleeps 12
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Downtown 123
No detail was overlooked in the design of this stunning five-bedroom home set on the hill. This home offers comfort and style and features rich counte... Read More
June 2027
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    1 2 3 4 $25,000 5
6 7 8 9 10 11 $25,000 12
13 14 15 16 17 18 $31,000 19
20 21 22 23 24 25 $31,000 26
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        1 2 $38,500 3
4 5 6 7 8 9 $38,500 10
11 12 13 14 15 16 $38,500 17
18 19 20 21 22 23 $38,500 24
25 26 27 28 29 30 $40,000 31
August 2027
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1 2 3 4 5 6 $40,000 7
8 9 10 11 12 13 $40,000 14
15 16 17 18 19 20 $40,000 21
22 23 24 25 26 27 $40,000 28
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Discover this stunning, rental home with a new pool (2026) in the heart of Katama tucked away on a private street. Designed with comfort and style in mind, this spacious retreat offers ample room for friends and family to unwind, along with large gathering spaces perfect for shared moments. The main level boasts a vast, modern kitchen, dining area,
$12,250.00 - $27,500.00 / per week + taxes and fees
Beds 5 beds
Baths 5 Full, 1 Half Bath
Sleeps sleeps 12
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Katama 610
Discover this stunning, rental home with a new pool (2026) in the heart of Katama tucked away on a private street. Designed with comfort and style in ... Read More
June 2027
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    1 2 3 4 $14,000 5
6 7 8 9 10 11 $14,000 12
13 14 15 16 17 18 $17,500 19
20 21 22 23 24 25 $20,000 26
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25 26 27 28 29 30 $27,500 31
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15 16 17 18 19 20 $24,750 21
22 23 24 25 26 27 $17,500 28
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