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 53 properties available
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
Su Mo Tu We Th Fr Sa
    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
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 $27,500 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 $24,750 21
22 23 24 25 26 27 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out

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
$8,000.00 - $18,000.00 / 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
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
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $8,000 5
6 7 8 9 10 11 $10,000 12
13 14 15 16 17 18 $10,000 19
20 21 22 23 24 25 $10,000 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $12,500 3
4 5 6 7 8 9 $15,000 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 $18,000 21
22 23 24 25 26 27 $15,000 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out

Immerse yourself in island luxury and play at this spectacular retreat. Designed for relaxation and fun, this home offers multiple spaces to gather—both indoors and out—surrounded by meticulous craftsmanship and upscale comfort. You'll find beautifully detailed paneling, coffered ceilings, custom lighting, and an abundance of natural light that cre
$20,000.00 - $36,000.00 / per week + taxes and fees
Beds 4 beds
Baths 4 Full, 2 Half Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown 7772
Immerse yourself in island luxury and play at this spectacular retreat. Designed for relaxation and fun, this home offers multiple spaces to gather—bo... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $21,000 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 $29,000 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $29,000 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 $36,000 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out

Located approximately 0.05 miles from the heart of downtown Edgartown, this beautifully designed and elegantly furnished five-bedroom coastal farmhouse offers a spacious first-floor living area. The large chef's kitchen features a prep island, granite countertops, Le Creuset cookware, a wine fridge, two dishwashers, and commercial-grade stainless s
$14,000.00 - $35,000.00 / 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 522
Located approximately 0.05 miles from the heart of downtown Edgartown, this beautifully designed and elegantly furnished five-bedroom coastal farmhous... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out

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
$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
Su Mo Tu We Th Fr Sa
    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      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 3
4 5 6 7 8 9 $20,000 10
11 12 13 14 15 16 $20,000 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
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
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out

Tucked away on 20 acres along the shores of Vineyard Sound, Chip Chop is one of Martha's Vineyard's most iconic and storied properties. Originally built in the 1940s for Broadway star Katharine Cornell, this extraordinary beachfront compound has welcomed generations of notable guests from the worlds of theater, film, literature, and politics. Surro
$100,000.00 - $150,000.00 / per week + taxes and fees
Beds 9 beds
Baths 9 Full, 1 Half Bath
Sleeps sleeps 16
Pet Friendly Pets Considered
Not Pet Friendly No Events/Gatherings
Vineyard Haven 907
Tucked away on 20 acres along the shores of Vineyard Sound, Chip Chop is one of Martha's Vineyard's most iconic and storied properties. Originally bui... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $150,000 5
6 7 8 9 10 11 $150,000 12
13 14 15 16 17 18 $150,000 19
20 21 22 23 24 25 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out

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
Hot HOT 15
$25,000.00 - $75,000.00 / per week + taxes and fees
Beds 7 beds
Baths 7 Full, 1 Half Bath
Sleeps sleeps 14
Pet Friendly Pets Considered
Not Pet Friendly No Events/Gatherings
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
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $50,000 5
6 7 8 9 10 11 $50,000 12
13 14 15 16 17 18 $50,000 19
20 21 22 23 24 25 $50,000 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $75,000 3
4 5 6 7 8 9 $75,000 10
11 12 13 14 15 16 $75,000 17
18 19 20 21 22 23 $75,000 24
25 26 27 28 29 30 $75,000 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $75,000 7
8 9 10 11 12 13 $75,000 14
15 16 17 18 19 20 $75,000 21
22 23 24 25 26 27 $75,000 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out

This exquisite residence boasts approximately 7,900 square feet of elegantly designed living space situated in an exceptional location. Encircled by Herring Creek Farm, the property offers exclusive access to a private dock and a secluded beach, providing a rare combination of seclusion and proximity to South Beach and Edgartown Village. Within the
Hot HOT 11
$45,000.00 - $65,000.00 / per week + taxes and fees
Beds 6 beds
Baths 7 Full, 2 Half Bath
Sleeps sleeps 14
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Katama 524
This exquisite residence boasts approximately 7,900 square feet of elegantly designed living space situated in an exceptional location. Encircled by H... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $45,000 5
6 7 8 9 10 11 $45,000 12
13 14 15 16 17 18 $45,000 19
20 21 22 23 24 25 $55,000 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $55,000 3
4 5 6 7 8 9 $65,000 10
11 12 13 14 15 16 $65,000 17
18 19 20 21 22 23 $65,000 24
25 26 27 28 29 30 $65,000 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $65,000 7
8 9 10 11 12 13 $65,000 14
15 16 17 18 19 20 $65,000 21
22 23 24 25 26 27 $45,000 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out

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
$11,700.00 - $32,500.00 / 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
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
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $16,300 5
6 7 8 9 10 11 $18,600 12
13 14 15 16 17 18 $23,300 19
20 21 22 23 24 25 $30,000 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $32,500 3
4 5 6 7 8 9 $30,000 10
11 12 13 14 15 16 $30,000 17
18 19 20 21 22 23 $32,500 24
25 26 27 28 29 30 $32,500 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $32,500 7
8 9 10 11 12 13 $32,500 14
15 16 17 18 19 20 $32,500 21
22 23 24 25 26 27 $26,700 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out

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
Su Mo Tu We Th Fr Sa
    1 2 3 4 $10,000 5
6 7 8 9 10 11 $10,000 12
13 14 15 16 17 18 $15,000 19
20 21 22 23 24 25 $16,000 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $19,000 3
4 5 6 7 8 9 $19,000 10
11 12 13 14 15 16 $19,000 17
18 19 20 21 22 23 $19,000 24
25 26 27 28 29 30 $19,000 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $19,000 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out

Welcome to this stunning 5-bedroom, 4.5-bathroom home located just outside Edgartown Village. This remarkable property is the ideal retreat for groups of up to 12 guests. Upon entering, you'll be welcomed by a spacious open-concept layout that seamlessly combines the kitchen, dining, and living areas. With lofty ceilings and an abundance of natural
$27,500.00 - $35,000.00 / per week + taxes and fees
Beds 5 beds
Baths 4 Full, 2 Half Bath
Sleeps sleeps 12
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Downtown 9
Welcome to this stunning 5-bedroom, 4.5-bathroom home located just outside Edgartown Village. This remarkable property is the ideal retreat for groups... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 $35,000 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out

Edgartown 7747
... Read More
June 2027
Su Mo Tu We Th Fr Sa
    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
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $30,000 3
4 5 6 7 8 9 $30,000 10
11 12 13 14 15 16 $30,000 17
18 19 20 21 22 23 $30,000 24
25 26 27 28 29 30 $32,000 31
August 2027
Su Mo Tu We Th Fr Sa
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
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out

Tell us what you're looking for and someone will contact you with available options.

I agree