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 VMOS-02
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:8
    • Bath:4.0
    • Sleeps:18
  • Description:
    Point B Exclusive - Villa Rosa is one of the most prominent Victorian mansions in Oak Bluffs — known as much for... Read More
  • 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 $5,000 - $14,000/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:
    Point B Exclusive - This freshly renovated Luxurious Contemporary combines water views out to Sengekontacket Pond from... 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 MJOR-29
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:3
    • 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

Dreamer's Getaway In Oak Bluffs $4,700 - $8,000/week

  • Property Highlights
    Unit Code: OB MCUR-25
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath:4.5
    • Sleeps:9
  • Description:
    Point B Exclusive - Dreamer's Getaway is a newly built Coastal Contemporary stylishly outfitted throughout, and... 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 JGLE-23
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath:3.0
    • Sleeps:8
  • Description:
    Point B Exclusive - Conveniently located near The Lagoon and Eastville Beach, this large Oak Bluffs Colonial has been... 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 BFLO-48
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:6
    • Bath:9.5
    • Sleeps:16
  • Description:
    This deluxe new compound at The Preserve makes a grand multi-generation or larger group Vineyard getaway destination.... Read More
  • 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