Vineyard Haven Vacation Rentals

Vineyard Haven, Martha’s Vineyard’s primary port town, is the perfect place for vacation rental guests who want to be close the action. While staying in a Vineyard Haven vacation rental, you have direct access to the waterfront and Vineyard Haven’s many fun events, world-famous restaurants, and classic bars. Vacations in Vineyard Haven are full of excitement and fun on the water, and going out in Vineyard Haven after a day at the beach gives you the classic Martha’s Vineyard experience.

 

 

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Cozy Sunny 3 Bedroom Contemporary, Spacious Deck, Situated in a Quiet Neighborhood just on the outskirts of Vineyard Haven Village Center

Located on a quiet residential circle in Vineyard Haven, this pristine sweet home with oversized windows is contemporary, yet rustic with exposed wooden beams and a cathedral ceiling.  New natural travertine...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $2,500
June 2025
SuMoTuWeThFrSaWeek
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$2,400
29
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 $2,500
July 2025
SuMoTuWeThFrSaWeek
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$2,500
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$2,500
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$2,500
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$2,500
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 $2,500
August 2025
SuMoTuWeThFrSaWeek
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$2,500
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$2,770
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$2,770
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$2,770
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$2,320
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September 2025
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Clean Fee: 
$200 per week
Tax: State & Local: 
11.7
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Mink Meadow Guest Cottage, Overlooks Golf Course, Walk to Beach 5 min walk from House, Mink Meadows Golf Course, 1 mile to Clubhouse

Cozy guest cottage with designer touches throughout. As the guest cottage to the main house, this adorable cottage is private from the main house and has its own drive and...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$10 - $2,100
June 2025
SuMoTuWeThFrSaWeek
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$1,900
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$1,900
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$1,900
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$1,900
29
30
 $2,100
July 2025
SuMoTuWeThFrSaWeek
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$2,100
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$2,100
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$2,100
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$2,100
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 $2,100
August 2025
SuMoTuWeThFrSaWeek
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$2,100
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$2,100
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$2,100
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$2,100
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$2,100
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 $1,900
September 2025
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$1,900
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$1,900
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$1,900
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$1,900
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 $1,900
Clean Fee: 
$150 per week
Tax: State & Local: 
11.7
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Spectacular Waterfront in exclusive Makonikey area, Ocean Views and Breathtaking Sunsets, Private Beach, Private Location

Relaxed waterfront home with sweeping water views and very private location, yet just a 10-minute drive to town, fine dining, shopping, galleries, and movies  This is a classic, casual and comfortably furnished...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$10 - $10
June 2025
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July 2025
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31
 $11,000
August 2025
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$11,000
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$11,000
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$11,000
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$11,000
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September 2025
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Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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Outer Harbor Waterfront, Private Sandy Beach, Lush Gardens and Large Yard, Magnificent Water Views

Relax and enjoy the picturesque views of the outer harbor, with its plethora of boats going by each day, from the screened Gazebo, porch, and patio areas. The wide, sandy private beach...Read more

Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$10 - $10
June 2025
SuMoTuWeThFrSaWeek
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$4,600
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$5,000
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$5,000
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$8,000
29
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 $8,250
July 2025
SuMoTuWeThFrSaWeek
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$8,250
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$8,250
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$8,250
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$9,100
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 $9,100
August 2025
SuMoTuWeThFrSaWeek
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$9,100
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$9,150
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$9,200
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$9,200
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$8,200
31
 $4,900
September 2025
SuMoTuWeThFrSaWeek
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$4,900
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$4,900
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$4,900
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$4,900
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 $4,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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Stunning Historic Home, Nicely Renovated with Luxury Details throughout, AC, View of Harbor from 2nd Level Porch

Quintessential, historic in-town Vineyard home, just steps from the beach and ferry.  Water views of Vineyard Haven Harbor. This totally renovated house is designed to create the perfect Vineyard vacation. ...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $10
June 2025
SuMoTuWeThFrSaWeek
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$5,000
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$5,000
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$5,000
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$5,000
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 $6,000
July 2025
SuMoTuWeThFrSaWeek
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$6,000
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$6,000
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$6,000
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$6,700
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 $7,300
August 2025
SuMoTuWeThFrSaWeek
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$7,300
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$7,300
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$7,300
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$7,300
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$7,000
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 $5,700
September 2025
SuMoTuWeThFrSaWeek
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$5,700
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$5,700
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$5,700
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$5,700
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30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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Light Filled, Stylish Cape Home, Ideal Central Location to Vineyard Haven, Oak Bluffs, Edgartown and Public Beaches.

Sure to please, this lovely all-new custom Cape is bordered by lawn and tall oaks and features a spacious open floor plan in the main living level with a dormered...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $10
June 2025
SuMoTuWeThFrSaWeek
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 $4,400
July 2025
SuMoTuWeThFrSaWeek
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$4,400
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$4,400
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$4,400
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$4,700
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 $5,550
August 2025
SuMoTuWeThFrSaWeek
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$5,550
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$5,550
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$5,550
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$5,550
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$4,500
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September 2025
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Clean Fee: 
$380 per week
Tax: State & Local: 
11.7
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Perfect Beach Front Cottage. Expansive Water Views, Gorgeous Sunsets, Pristine Modern Interior.

Privately nestled atop a dune with breathtaking views and just steps from a private swimming beach. This immaculate 2 bedroom, 1 bath beachfront cottage offers a tastefully furnished interior with sun-filled rooms...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$10 - $10
June 2025
SuMoTuWeThFrSaWeek
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$5,250
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$5,250
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$5,750
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$6,250
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 $6,750
July 2025
SuMoTuWeThFrSaWeek
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$6,750
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$6,750
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$6,750
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$6,750
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 $6,750
August 2025
SuMoTuWeThFrSaWeek
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$6,750
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$6,750
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$6,750
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$6,750
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$6,250
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 $5,750
September 2025
SuMoTuWeThFrSaWeek
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$5,750
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$5,250
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$4,750
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$4,750
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 $4,500
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
Add Favorite
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Beautiful 3 Bedroom, 3.5 bath Home, Bluestone Patio with Outdoor Dining & Grill , Lovely Landscaped Yard. Situated on Quiet Street, Walk to Town
Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
3
Baths: 
3
Price Range:
$10 - $10
June 2025
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July 2025
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 $8,600
August 2025
SuMoTuWeThFrSaWeek
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$8,600
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$8,600
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$8,600
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$17,500
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$8,800
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September 2025
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

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