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 54 properties available
Stunning Waterfront Retreat - West Tisbury, Martha's Vineyard. This spectacular residence sits on 7.9 acres with over 600 feet of pristine waterfrontage on Jennie's Cove. Designed for modern island living, the main house features a spacious open-concept kitchen, dining, and living area with expansive views of the water. The main house features thre
$15,400.00 - $20,400.00 / per week + taxes and fees
Beds 3 beds
Baths 3 Full, 1 Half Bath
Sleeps sleeps 6
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
West Tisbury 100050
Stunning Waterfront Retreat - West Tisbury, Martha's Vineyard. This spectacular residence sits on 7.9 acres with over 600 feet of pristine waterfronta... Read More
June 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $17,400 6
7 8 9 10 11 12 $18,400 13
14 15 16 17 18 19 $18,400 20
21 22 23 24 25 26 $20,400 27
28 29 30        
July 2026
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 $20,400 25
26 27 28 29 30 31  
August 2026
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

Discover this stunning, rental home 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, living room, office, a
🚢 Ferry Tickets
🚢 Ferry Tickets
August 22nd - August 29th
$12,250.00 - $25,000.00 / 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 Katama 610
Discover this stunning, rental home in the heart of Katama tucked away on a private street. Designed with comfort and style in mind, this spacious ret... Read More
June 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $14,000 6
7 8 9 10 11 12 $14,000 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30        
July 2026
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 2026
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 $22,500 22
23 24 25 26 27 28 $17,500 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
Hot HOT 12
$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 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $15,000 6
7 8 9 10 11 12 $15,000 13
14 15 16 17 18 19 $15,000 20
21 22 23 24 25 26 $20,000 27
28 29 30        
July 2026
Su Mo Tu We Th Fr Sa
      1 2 3 $20,000 4
5 6 7 8 9 10 $20,000 11
12 13 14 15 16 17 $20,000 18
19 20 21 22 23 24 25
26 27 28 29 30 31  
August 2026
Su Mo Tu We Th Fr Sa
            1
2 3 4 5 6 7 8
9 10 11 12 13 14 $20,000 15
16 17 18 19 20 21 $18,000 22
23 24 25 26 27 28 $15,000 29
30 31          
Prev
Next
Available
Unavailable
Check-In
Check-Out

Waterfront six bedroom main and guest house in a lovely sought after Oak Bluffs association of Hart Haven. The main house is exquisitely and architecturally designed with two primary suites, a chef's Kitchen, open and sprawling dining and living spaces all on the main level with peaceful water views of Farm Pond and a distance view of the Atlantic
$9,500.00 - $23,500.00 / per week + taxes and fees
Beds 6 beds
Baths 5 Full, 2 Half Bath
Sleeps sleeps 12
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Oak Bluffs 807
Waterfront six bedroom main and guest house in a lovely sought after Oak Bluffs association of Hart Haven. The main house is exquisitely and architect... Read More
June 2026
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 2026
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 2026
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

The "Preserve" off County Road at its finest! Five modern bedrooms, fully air conditioned, expanded farmhouse with inspiration and fixtures from Restoration Hardware and Waterworks. Modern design with soft tones of whites, ecru, and warm grays used throughout. Wide plank wood flooring, chevron wood floors in the kitchen, dining room, and den. The
$18,500.00 - $32,000.00 / per week + taxes and fees
Beds 5 beds
Baths 5 Full, 1 Half Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Oak Bluffs 846
The "Preserve" off County Road at its finest! Five modern bedrooms, fully air conditioned, expanded farmhouse with inspiration and fixtures from Rest... Read More
June 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $24,500 6
7 8 9 10 11 12 $24,500 13
14 15 16 17 18 19 $24,500 20
21 22 23 24 25 26 27
28 29 30        
July 2026
Su Mo Tu We Th Fr Sa
      1 2 3 4
5 6 7 8 9 10 $30,500 11
12 13 14 15 16 17 $30,500 18
19 20 21 22 23 24 25
26 27 28 29 30 31  
August 2026
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

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
$18,000.00 - $22,000.00 / per week + taxes and fees
Beds 4 beds
Baths 3 Full Bath
Sleeps sleeps 9
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
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
June 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $18,000 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 2026
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 2026
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

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
$22,000.00 - $35,000.00 / per week + taxes and fees
Beds 4 beds
Baths 5 Full, 1 Half Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
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
June 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $25,000 6
7 8 9 10 11 12 $25,000 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30        
July 2026
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 2026
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

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 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $15,000 6
7 8 9 10 11 12 $15,000 13
14 15 16 17 18 19 $20,000 20
21 22 23 24 25 26 27
28 29 30        
July 2026
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 2026
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

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
$13,200.00 - $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 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $11,000 6
7 8 9 10 11 12 $11,000 13
14 15 16 17 18 19 $16,500 20
21 22 23 24 25 26 $19,800 27
28 29 30        
July 2026
Su Mo Tu We Th Fr Sa
      1 2 3 $19,800 4
5 6 7 8 9 10 $19,800 11
12 13 14 15 16 17 18
19 20 21 22 23 24 25
26 27 28 29 30 31  
August 2026
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

Glamorous waterfront property nestled within the prestigious area of South Water Street in downtown Edgartown. This harbor spectacular five bedroom six bathroom captains home has been re-constructed with luxury and comfort marking every corner of this property sheer elegance. Inside you will find a chef's kitchen equipped with stainless steel appli
Hot HOT 11
$18,000.00 - $58,000.00 / per week + taxes and fees
Beds 5 beds
Baths 6 Full, 1 Half Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Downtown 87
Glamorous waterfront property nestled within the prestigious area of South Water Street in downtown Edgartown. This harbor spectacular five bedroom si... Read More
June 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 6
7 8 9 10 11 12 $25,000 13
14 15 16 17 18 19 $46,000 20
21 22 23 24 25 26 27
28 29 30        
July 2026
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 2026
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 $58,000 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 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $16,300 6
7 8 9 10 11 12 $18,600 13
14 15 16 17 18 19 $23,300 20
21 22 23 24 25 26 27
28 29 30        
July 2026
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 2026
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 2026
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 $16,000 6
7 8 9 10 11 12 13
14 15 16 17 18 19 $24,000 20
21 22 23 24 25 26 27
28 29 30        
July 2026
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 2026
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

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

I agree