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Oak Bluffs Vacation Rentals

One of the island’s most popular destinations, Oak Bluffs offers a broad range of attractions for kids and adults, from ice cream parlors and an arcade to the dozens of shops, restaurants, and bars along and around Circuit Avenue. The town hosts annual special events, including late-summer fireworks at Ocean Park and Illumination Night, when Campground residents put thousands of unique and colorful Chinese lanterns on display. 

You can also view all of our Martha's Vineyard Vacation Rentals.  Or search for rentals in Edgartown, Edgartown Village, Katama, Chilmark, Vineyard Haven Tisbury, or West Tisbury.

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44 properties returned | Your Current Search: Location - Oak Bluffs

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discount tag Limited-Edition Luxury Short Stay

Introducing the Luxury Short Stay - A Rare Opportunity From Our Exclusive Vineyard Luxury Collection. Shorter 3 & 4-night escapes now available for May, June, and July. Unwind on your terms from midweek to long weekends. Email our rental team or give us a call 508.939.9422 

 

Luxurious Coastal-Style Living With Pool And Hot Tub In The Preserve $0 - $0/week

100 Collection
  • Property Highlights
    Unit Code: OB RSMI-16
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:5
    • Bath: 6.5
    • Sleeps:12
  • Description:
    POINT B EXCLUSIVE - This recently built luxury home features three floors of deluxe indoor living space, with nicely... Read More
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Modern Colonial Near The Lagoon $0 - $0/week

  • Property Highlights
    Unit Code: OB GASH-12
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:3
    • Bath: 3.5
    • Sleeps:6
  • Description:
    POINT B EXCLUSIVE - This recently built Modern Colonial has a stylish Vineyard vibe throughout, and is tucked away in a... Read More
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Luxurious Oak Bluffs Contemporary With Water Views $0 - $0/week

  • Property Highlights
    Unit Code: OB EVAN-07
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath: 4.5
    • Sleeps:8
  • Description:
    POINT B EXCLUSIVE - This freshly renovated Luxurious Contemporary combines water views out to Sengekontacket Pond from... Read More
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Coastal Farmhouse With Connected Carriage House $0 - $0/week

  • Property Highlights
    Unit Code: OB KMCD-09
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:5
    • Bath: 4.5
    • Sleeps:10
  • Description:
    POINT B EXCLUSIVE - This newly built Farmhouse with Connected Carriage House features a modern coastal-style with nice... Read More
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Modern Farmhouse In Central Oak Bluffs Neighborhood $0 - $0/week

  • Property Highlights
    Unit Code: OB EEXU-29
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:3
    • Bath: 3.5
    • Sleeps:8
  • Description:
    POINT B EXCLUSIVE - This newly-built Modern Farmhouse is tucked away in a quiet and centrally located neighborhood in... Read More
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Water View Cottage At Sunset Lake $0 - $0/week

  • Property Highlights
    Unit Code: OB MLLO-14
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:3
    • Bath: 2.0
    • Sleeps:6
  • Description:
    POINT B EXCLUSIVE -- This classic Oak Bluffs cottage sits at the edge of Sunset Lake and enjoys views across the Lake on... Read More
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Sengekontacket Contemporary With Water Views $0 - $0/week

  • Property Highlights
    Unit Code: OB SVIC-20
    Pets Considered: Yes
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath: 4.5
    • Sleeps:8
  • Description:
    **JUNE SPECIAL: SAVE $500/WEEK OFF OPEN WEEKS 5/31 - 6/21 | NEW RATES APPLIED ** POINT B EXCLUSIVE - Tucked away in the... Read More
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Contemporary Cape In Central Oak Bluffs $0 - $0/week

  • Property Highlights
    Unit Code: OB EEXU-71
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:3
    • Bath: 2.0
    • Sleeps:6
  • Description:
    POINT B EXCLUSIVE - This newly renovated Cape is quietly located in a convenient central Oak Bluffs neighborhood. Newly... Read More
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Chic Highlands Cottage In East Chop $0 - $0/week

  • Property Highlights
    Unit Code: OB RHAR-09
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:2
    • Bath: 2.0
    • Sleeps:6
  • Description:
    POINT B EXCLUSIVE - This sleekly renovated Cape is tucked away in the Highlands section of East Chop. The single level... Read More
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Modern Farmhouse In Meadow View Farms $0 Per Week

  • Property Highlights!
    Unit Code: OB ATUR-19
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath:4.5
    • Sleeps:8
  • Description:
    Nestled in the quiet Meadow View Farms area, near Farm Neck Golf Course in Oak Bluffs, this new Modern Farmhouse is... Read More
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Waterfront Retreat With Pool, And Private Beach $0 Per Week

  • Property Highlights!
    Unit Code: OB LPER-385
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath:4.5
    • Sleeps:10
  • Description:
    This waterfront home features three levels of striking indoor living space, nicely integrated with outdoor living spaces... Read More
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Mid-Century Modern Chic Beach Retreat $0 Per Week

  • Property Highlights!
    Unit Code: OB MTER-18
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath:2.0
    • Sleeps:8
  • Description:
    This Mid-Century Modern home near Sengekontacket, has been sleekly redesigned and renovated into a Chic Beach Retreat. ... Read More
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