Oak Bluffs Vacation Rentals

Oak Bluffs is a beautiful peninsula on the north eastern coast of Martha’s Vineyard that is bordered by Nantucket Sound. Renting a vacation home in Oak Bluffs gives you so many options. Our list of vacations rentals include luxury waterfront properties with exceptional views of the sound and quaint Victorian homes that allow you to glimpse deeply into Martha’s Vineyard’s historic past. Vacationing in Oak Bluffs is like taking a trip back in time. Ocean air and private beaches make you feel as though you have Martha’s Vineyard all to yourself.

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Updated East Chop Area Summer Retreat, Great Proximity to Town Center and Beaches, Cottage Styling with All the Modern Amenities, Central A/C. Covered Porch and Open Patio Areas.

Visitors will enjoy this delightful &  comfortable 4 bedroom, 3 bath home in the desirable East Chop area of Oak Bluffs. 

Relax in the breeze with your morning coffee on the front...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$0 - $0
June 2027
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 $5,350
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Clean Fee: 
$500 per week
Tax: State & Local: 
14.45
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MAHAB

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Property Details
Sweet Updated 3 Bedroom Home, Nicely Tucked in Lightly Wooded Area, Central Location, Beaches and Towns just a short Drive!

Lovely reverse contemporary home with a large deck, outdoor dining, and grill area. The upper level of this home features an open kitchen, living, and dining area stylishly furnished.  Nicely equipped kitchen...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
1
Price Range:
$0 - $0
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Clean Fee: 
$300 per week
Tax: State & Local: 
14.45
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LANLL

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Property Details
Outstanding Waterfront Home & Guest House, Panoramic Views, Beach on the Lagoon, 5 Bedrooms, 4 Baths, AC

Gorgeous Expansive Waterfront Main & Guest Cottage, perfect for a multigenerational family vacation.  Spectacular views across and up the lagoon, this pristine home and guest cottage sits on just under two...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
5
Baths: 
4
Price Range:
$0 - $0
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Clean Fee: 
$600 per week
Tax: State & Local: 
14.45

Two Week Minimum Stay Required per Owner

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NEWMJ

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Property Details

Newly update mid-century modern beach house set in the private community of homes surrounding Sengekontacket pond. The cozy summer cottage offers indoor and outdoor living at its best with a...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
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Clean Fee: 
$400 per week
Tax: State & Local: 
14.45
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ROSKH

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Property Details
East Chop Classic Waterfront Home, Private Dock, Mooring Available, Spectacular Sunsets, For 2027 this Home is Under the code MUCCJ

Experience refined coastal living at this exceptional cottage- style waterfront retreat in the coveted East Chop area of Oak Bluffs. 

This idyllic waterfront summer sanctuary is poised to create cherished...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$0 - $0
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Clean Fee: 
$650 per week
Tax: State & Local: 
14.45

Owner reduced rate for weeks 8/15 & 8/22 - see calendar for adjusted rates

This property is under a new code for the 2027 season.  Please see MUCCJ

 

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DUREJ

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Property Details

This luxuriously updated tri-level condo retreat at Quail Run in the community of homes known as Sengekontacket, has been transformed, bringing a fresh, coastal feel to every corner. The end...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
1
Price Range:
$0 - $0
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Clean Fee: 
$400 per week
Tax: State & Local: 
14.45

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