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
    • 4Bedrooms:
    • 2.5Baths:
    • 8Sleeps:
  • Description:
    BR 1 - Two twins, BR 2 - Two twins, BR 3 - Two twins, BR 4 - Queen...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: No
    • 3Bedrooms:
    • 2.0Baths:
    • 8Sleeps:
  • Description:
    BR1 King master, hall bathroom of tub and shower, first floor, BR2 (3) Twin beds, second floor, BR3 (3/4) bed (over-size...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: No
    • 5Bedrooms:
    • 5.5Baths:
    • 10Sleeps:
  • Description:
    BR1 King Bedroom en-suite with shower on main floor, BR2 Queen Bedroom flat screen TV second floor, BR3 (2)Twin beds on ...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 5Bedrooms:
    • 2.5Baths:
    • 10Sleeps:
  • Description:
    Main House - BR1 King Bedroom en-suite of tub shower first floor, BR2 Twin beds second floor, BR3 (2) Double beds second...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: No
    • 4Bedrooms:
    • 3.0Baths:
    • 8Sleeps:
  • Description:
    BR1 Master with King and Ensuite Bath with Tub and Shower Combination and Doors to Private Deck, First Floor. BR2 Twin O...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 1Bedrooms:
    • 1.0Baths:
    • 4Sleeps:
  • Description:
    Queen Bed in living area, BR1 Queen futon. Hall bathroom of tub and shower....Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: Yes, with approval
    • 4Bedrooms:
    • 3.0Baths:
    • 8Sleeps:
  • Description:
    BR1 Master King, first floor with split a/c unit, en suite bathroom of separate tub and shower and egress to yard. Seco...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: Tuesday
    Pets Allowed: No
    • 3Bedrooms:
    • 2.5Baths:
    • 6Sleeps:
  • Description:
    BD#1: Master with waterviews, Queen bed, television, ensuite bath with steam shower and private balcony. BD#2: Queen, wa...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 3Bedrooms:
    • 3.5Baths:
    • 8Sleeps:
  • Description:
    ...Read More
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