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 Edgartown, Edgartown Village, Katama, Chilmark, Vineyard Haven Tisbury, or West Tisbury.

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43 properties returned | Your Current Search: Location - Oak Bluffs

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discount tag Available Peak Weeks August 2025


Some of the biggest events of the summer on Martha's Vineyard are moving a week later next year. The Agricultural Fair, Illumination Night, and the Oak Bluffs Fireworks are ALL moving to the third week of August in 2025 (August 15 - 24). This past summer, all those peak week events occurred during the second week. Given the popularity of that week, plus the other big events of August, lots of Martha's Vineyard vacation rentals are booked by repeat renters or get rented quickly. Good news, we've got a great collection of luxury homes that are available for next August. You can browse the collection here or call our Rental Team to explore your options 508.939.9422

Grand Coastal-Style Estate In The Preserve With Pool And Hot Tub $10,000 - $30,000/week

  • 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
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Luxurious Oak Bluffs Contemporary With Water Views $5,500 - $13,000/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
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Coastal Farmhouse With Connected Carriage House $6,600 - $12,500/week

  • 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
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discount tag July 4th Week


The fourth of July week on Martha's Vineyard is one of the icon weeks to enjoy the Vineyard. During the day, there is the quintessential July 4th parade in Edgartown followed by the fireworks over Edgartown Harbor and Edgartown Lighthouse. Both events truly epic and totally Martha's Vineyard. We have a curated collection of the best vacation rentals on Martha's Vineyard that are available during this magic week (July 4th - July 14th). From Edgartown and Katama, to Oak Bluffs and Vineyard Haven, from in-town to luxury homes with pools -- there are great options! Our Rental Team is here and ready to help you. Please reach out to us by phone 508-939-9422 or email.

Sengekontacket Contemporary With Water Views $4,000 - $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
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discount tag July 4th Week


The fourth of July week on Martha's Vineyard is one of the icon weeks to enjoy the Vineyard. During the day, there is the quintessential July 4th parade in Edgartown followed by the fireworks over Edgartown Harbor and Edgartown Lighthouse. Both events truly epic and totally Martha's Vineyard. We have a curated collection of the best vacation rentals on Martha's Vineyard that are available during this magic week (July 4th - July 14th). From Edgartown and Katama, to Oak Bluffs and Vineyard Haven, from in-town to luxury homes with pools -- there are great options! Our Rental Team is here and ready to help you. Please reach out to us by phone 508-939-9422 or email.

Modern Farmhouse In Central Oak Bluffs Neighborhood $5,600 - $8,600/week

  • 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
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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
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Contemporary Cape In Central Oak Bluffs $3,300 - $7,000/week

  • 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
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Architect Designed Getaway In Bayes Hill $3,900 - $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
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Water View Compound At Inkwell Beach In OaK Bluffs $12,000 - $38,000 Per Week

  • 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
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Modern Architectural Gem With Pool, Hot Tub And Water Views $17,700 - $37,500 Per Week

  • 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
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Architect-Designed Luxury Compound With Pool And Pool House $17,500 - $34,000 Per Week

  • 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
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Modern Designed Living At The Preserve With Pool And Hot Tub $14,000 - $34,000 Per Week

  • 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
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