Oak Bluffs Rentals


Our Oak Bluffs rentals are the prime destination for your summer vacation to Martha's Vineyard. Its fun and active ambiance really opens up with the arrival of Memorial weekend and stays in full swing until Columbus weekend. It has historically been a summer destination dating back to the mid 1800’s when the camp ground cottages were developed as a Methodist summer retreat which actually started with camp sites and developed into the quaint, colorful gingerbread cottages that we see today.

For attractions near your Oak Bluffs vacation rentals, visit the town center,  located on the harbor where you will find a high energy level with hundreds of boats coming and going. Circuit Avenue is the commercial heart of Oak Bluffs. It has ice cream and sunscreen, coffee stands and souvenir shops. It has Reliable Self-Serve Market, family owned and operated, and Giordano's Restaurant and Clam Bar, offering up family style meals since 1930. It has Back Door Doughnuts (on a summer's night, between 9 p.m. and 12:30 a.m., buy them fresh from the oven in the parking lot behind Reliable Market.). Circuit Avenue starts with the Flying Horses Carousel, the nation's oldest operating platform carousel and a National Historical Landmark owned by the Martha's Vineyard Preservation Trust and ends with the start of the Art District on the other end. Oak Bluffs also hosts the "summer” steamship authority terminal adding to its high summer foot traffic.

There are many residential areas outside of the downtown that offer quiet privacy for your summer vacation yet have easy access to downtown Oak Bluffs, Edgartown and Vineyard Haven. Contact us for more information about any of the Oak Bluffs rentals on our site.


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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 5Bedrooms:
    • 2.5Baths:
    • 12Sleeps:
  • Description:
    Main level: BR1 Queen with a sink, BR2 Queen with a sink, shared hall bathroom of tub and shower, Powder room on this le...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 3Bedrooms:
    • 2.0Baths:
    • 6Sleeps:
  • Description:
    BR1 Queen, en suite, BR2 (2) Twins, hall bath, BR3 Trundle with (2) Twins en suite....Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 3Bedrooms:
    • 2.5Baths:
    • 12Sleeps:
  • Description:
    BR1 Queen, second floor with full bathroom, BR2 (2) Twin beds, lower level with shared full hall bath, BR3 (2) Double be...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 6Bedrooms:
    • 5.5Baths:
    • 15Sleeps:
  • Description:
    BD1 King with Bath (Tub / Shower), first floor, BD2 Twin Over Full Bunks, first floor, BD3 Queen with Bath (Tub / Shower...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: No
    • 4Bedrooms:
    • 3.0Baths:
    • 9Sleeps:
  • Description:
    BR1 Queen with private bath with jacuzzi tub, first floor, BR2 (1) set of Bunks and (1) Twin first floor, BR3 Queen firs...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: No
    • 4Bedrooms:
    • 3.5Baths:
    • 8Sleeps:
  • Description:
    BR1 Queen bedroom en suite of separate shower and separate tub and small balcony, BR2 Queen bedroom, BR3 (2) Twin beds, ...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 4Bedrooms:
    • 2.5Baths:
    • 8Sleeps:
  • Description:
    BR#1 King bedroom ensuite on the second level, BR#2 Queen lower level, BR#3 Queen lower level, BR#4 (2) Twins lower leve...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: No
    • 4Bedrooms:
    • 7.0Baths:
    • 10Sleeps:
  • Description:
    BR1 King Master Suite, en suite bath w/ jacuzzi tub and glass shower stall, main level, BR2 King, en suite bath w/ tub/s...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 6Bedrooms:
    • 7.0Baths:
    • 12Sleeps:
  • Description:
    BR1 King en suite of large walk in shower first floor, water view and flat screened TV, BR2 (2) Twin beds. Hall bathroo...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 3Bedrooms:
    • 2.0Baths:
    • 6Sleeps:
  • Description:
    BR1 Queen, main floor, hall bathroom with tub and shower, BR2 (2) Twin beds, main floor, BR3 (2) Twin beds, main floor, ...Read More
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