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.

Map All Results

  • Property Highlights
    Unit Code: OB RSMI-16
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:5
    • Bath:6.5
    • Sleeps:12
  • Description:
    **SUMMER SPECIAL: SAVE UP TO $4,000/WEEK OFF OPEN WEEKS JUNE THRU SEPTEMBER | NEW RATES IN** Point B Exclusive - This... Read More
  • Property Highlights
    Unit Code: OB EVAN-07
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath:4.5
    • Sleeps:8
  • Description:
    **JULY SPECIAL: SAVE $1,000 OFF OPEN WEEKS | NEW RATES PROGRAMMED + TRANSFERABLE FERRY TICKETS** Point B Exclusive -... 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:
    Point B Exclusive - FERRY TICKETS - Tucked away in the desirable Waterview Farm enclave on Sengekontacket Pond, this... 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

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 EEXU-71
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:3
    • Bath:2.0
    • Sleeps:6
  • Description:
    Point B Exclusive - FERRY TICKETS - This newly renovated Cape is quietly located in a convenient central Oak Bluffs... Read More
  • Property Highlights
    Unit Code: OB MSKE-41
    Pets Considered: Yes
    Town/Area: Oak Bluffs
    • Bedrooms:3
    • Bath:2.5
    • Sleeps:8
  • Description:
    Point B Exclusive - This architect-designed home is tucked away back in the Bayes Hill enclave, surrounded by... Read More

Classic Cottage In Oak Bluffs $1,500 - $3,300/week

  • Property Highlights
    Unit Code: OB RCOL-01
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:2
    • Bath:1.0
    • Sleeps:6
  • Description:
    Point B Exclusive - This Classic Cottage is conveniently located in central Oak Bluffs with easy access into both... 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
  • 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
  • Property Highlights
    Unit Code: OB VBUT-09
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:9
    • Bath:5.5
    • Sleeps:18
  • Description:
    NEW FOR SUMMER 2024 - This water view Compound with a recently renovated six-Bedroom Main House and a brand new... Read More