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 EdgartownEdgartown VillageKatamaChilmarkVineyard Haven Tisbury, or West Tisbury.

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  • 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

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
  • 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
  • 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
  • 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

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
  • 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
  • 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

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
  • 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

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
  • 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