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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 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 recently built luxury home features three floors of deluxe indoor living space, with nicely... Read More

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

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
  • 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

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
  • 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

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

discount tag Third Week Of August

The third week of August has a new vibe this year. While the Ag Fair has moved to the second week of August, two of the most popular Vineyard events now take center stage: Illumination Night (August 19th) and the Oak Bluffs fireworks (August 21st). It's a great week to be on the Vineyard. We have a great collection of vacation rentals you can only book at Point B. Email us.

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 - This newly renovated Cape is quietly located in a convenient central Oak Bluffs neighborhood. Newly... Read More

discount tag July 4th Week

The fourth of July is quintessential Martha's Vineyard. Earlier in the day, the July 4th parade winds through Edgartown Village and then that night, fireworks over Edgartown Harbor and lighthouse. It's classic Vineyard all the way. We have a great collection of vacation rental options across the Island from in-town to near the beach to pools that are only available to book at Point B. You can email us or call the Rental Team to book 508.939.9424 Check The Collection.

Architect Designed Getaway In Bayes Hill $4,017 - $6,695/week

  • 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
  • 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 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
  • 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