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Oak Bluffs Vacation Rentals

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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 $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 - NEW FOR SUMMER 2021 - This freshly renovated Luxurious Contemporary combines water views out to... 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
  • 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 - BRAND NEW FOR SUMMER 2021 - This brand new Farmhouse with Connected Carriage House features a modern... 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 - BRAND NEW FOR SUMMER 2021 - The finishing touches are just being put on this newly-built Modern... Read More

Dreamer's Getaway In Oak Bluffs $3,600 - $7,700/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

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 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
  • Property Highlights
    Unit Code: OB BFLO-48
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:6
    • Bath:9.5
    • Sleeps:18
  • 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 LSMA-06
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:5
    • Bath:7.0
    • Sleeps:10
  • Description:
    This grand five-bedroom Compound at The Preserve has luxurious detailing and styling throughout, including an attached... Read More
  • Property Highlights
    Unit Code: OB LPER-385
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath:4.5
    • Sleeps:10
  • Description:
    This waterfront home features three levels of striking indoor living space, nicely integrated with outdoor living spaces... Read More