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:
    • 5.5Baths:
    • 10Sleeps:
  • Description:
    BR1 King master en suite of separate shower and soaking tub first floor, BR2 Queen en suite of shower stall second floor...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: No
    • 3Bedrooms:
    • 2.0Baths:
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  • Description:
    BR1 Queen en suite of large shower stall, BR2 (2) Twin beds, BR3 mini-cot, hall bathroom of tub and shower....Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: No
    • 3Bedrooms:
    • 2.5Baths:
    • 6Sleeps:
  • Description:
    BR1 King, en suite with shower only, BR2 Queen, shares hall bathroom of tub and shower, BR3 (2) Twin beds, shares hall ...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: No
    • 4Bedrooms:
    • 3.5Baths:
    • 8Sleeps:
  • Description:
    BR1 King en suite of tub and shower first floor, BR2 Queen first floor located behind the kitchen near the den, hall bat...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: 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
    • 4Bedrooms:
    • 2.0Baths:
    • 6Sleeps:
  • Description:
    BR1 Queen second floor, BR2 Double second floor, Hall Bath, BR3 Queen lower level, BR4 (1) Twin lower level, Hall Bath....Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 5Bedrooms:
    • 2.5Baths:
    • 10Sleeps:
  • Description:
    BR1 King master upper level shared bath with tub/shower, BR2 Double upper level, shared bath with BR 1, BR3 Queen lower ...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 3Bedrooms:
    • 2.5Baths:
    • 8Sleeps:
  • Description:
    BR1 King en suite shower stall first floor, BR2 Queen, second floor, BR3 (2) Queen beds with shared hall bathroom of tub...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 3Bedrooms:
    • 2.0Baths:
    • 8Sleeps:
  • Description:
    BR1 Queen first floor en suite shower stall, BR2 Double second floor, BR3 Double second floor, hall bath with claw-foot ...Read More
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