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

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Grand Coastal-Style Estate In The Preserve $10,500 - $22,500/week

  • 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 Grand Coastal-Style Estate is quietly tucked away in The Preserve, the desirable new enclave... Read More
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Sleek Contemporary In Hidden Cove $4,550 - $15,000/week

  • Property Highlights
    Unit Code: OB ABON-15
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:6
    • Bath:5.5
    • Sleeps:12
  • Description:
    Point B Exclusive - This sleek new Contemporary is tucked away in the Hidden Cove neighborhood, just off Sengekontacket... Read More
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Luxurious Oak Bluffs Contemporary With Water Views $6,000 - $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:
    **SUMMER SPECIAL: SAVE UP TO $2,000/WEEK OFF - ALL AVAILABLE WEEKS JUNE + JULY | NEW RATES ARE PROGRAMMED** Point B... Read More
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Coastal Farmhouse With Connected Carriage House $6,000 - $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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Sengekontacket Contemporary With Water Views $3,850 - $10,000/week

  • Property Highlights
    Unit Code: OB SVIC-20
    Pets Considered: Yes
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath:4.5
    • Sleeps:8
  • Description:
    NEW FOR SUMMER 2023 - Point B Exclusive - Tucked away in the desirable Waterview Farm enclave on Sengekontacket Pond,... Read More
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Sweet Retreat In Oak Bluffs $2,660 - $10,000/week

  • Property Highlights
    Unit Code: OB KMIN-03
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:3
    • Bath:3.5
    • Sleeps:6
  • Description:
    **SUMMER SPECIAL: SAVE UP TO 15% OFF OPEN JULY WEEKS & JUNTEENTH SPECIAL STAY 6/16 - 6/20 FOR $3,780**Point B Exclusive... Read More
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Modern Farmhouse In Central Oak Bluffs Neighborhood $2,520 - $8,500/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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Newly Renovated Luxury Getaway In Oak Bluffs $4,000 - $8,000/week

  • Property Highlights
    Unit Code: OB MJOR-29
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath:2.0
    • Sleeps:8
  • Description:
    Point B Exclusive -- This newly renovated in-town getaway sits just outside the hustle and bustle of downtown, 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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Architect Designed Getaway In Bayes Hill $2,730 - $6,000/week

  • Property Highlights
    Unit Code: OB MSKE-41
    Pets Considered: Yes
    Town/Area: Oak Bluffs
    • Bedrooms:3
    • Bath:2.5
    • Sleeps:8
  • Description:
    **SAVE UP TO 15% OFF OPEN JULY AND AUGUST WEEKS - NEW RATES HAVE BEEN PROGRAMMED IN** Point B Exclusive - This... Read More
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Hideaway At Meadow View Farm $2,100 - $6,000/week

  • Property Highlights
    Unit Code: OB MCHA-09
    Pets Considered: Yes
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath:3.0
    • Sleeps:8
  • Description:
    Point B Exclusive - This Vineyard Hideaway is tucked back in the desirable Meadow View Farms area of Oak Bluffs, and... Read More
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Modern Architectural Gem With Pool, Hot Tub And Water Views $17,700 - $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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