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

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Luxurious Coastal-Style Living With Pool And Hot Tub In The Preserve $10,500 - $30,000/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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Luxurious Oak Bluffs Contemporary With Water Views $7,000 - $14,000/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 $6,600 - $12,100/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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discount tag Rentals With Ferry Tickets

Car ferry tickets are in high demand, but some of our homeowners secured transferable tickets in advance. A limited number of round-trip weekend tickets ($356) are still available as an add-on at select vacation rentals.. Email or call us to book 508.939.9422

Sengekontacket Contemporary With Water Views $4,700 - $10,500/week

  • Property Highlights
    Unit Code: OB SVIC-20
    Pets Considered: Yes
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath: 4.5
    • Sleeps:8
  • Description:
    POINT B EXCLUSIVE - Tucked away in the desirable Waterview Farm enclave on Sengekontacket Pond, this newly outfitted... Read More
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Modern Farmhouse In Central Oak Bluffs Neighborhood $5,500 - $8,600/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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Modern Colonial Near The Lagoon $2,700 - $7,500/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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Water View Cottage At Sunset Lake $5,000 - $7,500/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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Contemporary Cape In Central Oak Bluffs $3,300 - $7,000/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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Modern Architectural Gem With Pool, Hot Tub And Water Views $6,195 - $37,500 Per Week

  • Property Highlights!
    Unit Code: OB CMAT-400
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:6
    • Bath:5.5
    • Sleeps:12
  • Description:
    Tucked back up a hill overlooking Lagoon Pond, this architect-designed Modern Gem enjoys grand indoor-outdoor living... Read More
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Architect-Designed Luxury Compound With Pool And Pool House $17,500 - $35,000 Per Week

  • Property Highlights!
    Unit Code: OB BFLO-48
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:6
    • Bath:9.5
    • Sleeps:16
  • Description:
    This deluxe compound at The Preserve makes a grand multi-generation or larger group Vineyard getaway destination. There... Read More
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Water View Compound At Inkwell Beach In OaK Bluffs $12,000 - $35,000 Per Week

  • Property Highlights!
    Unit Code: OB VBUT-09
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:9
    • Bath:5.5
    • Sleeps:18
  • Description:
    This water view Compound with a recently renovated six-Bedroom Main House and a newly built three-Bedroom Guest House... Read More
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Modern Designed Living At The Preserve With Pool And Hot Tub $16,000 - $34,000 Per Week

  • Property Highlights!
    Unit Code: OB PMOR-12
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath:6.5
    • Sleeps:8
  • Description:
    This luxurious home at The Preserve is designed for indoor-outdoor living, with modern styling throughout its deluxe... Read More
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