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:
    • 3.5Baths:
    • 8Sleeps:
  • Description:
    BR1 Queen second floor, BR2 set of Bunk beds and Double second floor, BR3 Queen Second floor with en suite bath (shower ...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: N/A
    Pets Allowed: No
    • 2Bedrooms:
    • 1.0Baths:
    • 4Sleeps:
  • Description:
    BR1 King, with flat screened TV, main level, BR2 (2) Twin beds, main level. Both bedrooms share a hall bathroom equipped...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: Yes, with approval
    • 3Bedrooms:
    • 1.0Baths:
    • 6Sleeps:
  • Description:
    One Level Bungalow - BR1 Queen, BR2 Queen, BR2 Trundle all share hall bath w Tub/Shower Combo. There are no Bureaus in t...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: No
    • 4Bedrooms:
    • 2.0Baths:
    • 10Sleeps:
  • Description:
    BD 1: King Bed with Television, Private Porch and Views of the Atlantic Ocean and Farm Pond, Second Floor. BD 2: Queen B...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 1Bedrooms:
    • 1.0Baths:
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  • 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: No
    • 4Bedrooms:
    • 2.0Baths:
    • 6Sleeps:
  • Description:
    BR1 King en suite with shower stall, second floor, BR2 Queen first floor, BR3 (1) Twin bed first floor, BR4 (1) Twin bed...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:
    • 2.5Baths:
    • 8Sleeps:
  • Description:
    BR1 Queen Bedroom first floor, BR2 (2) Twin beds first floor, BR3 Twin Trundle first floor, BR4 Queen Bedroom with full ...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: N/A
    Pets Allowed: No
    • 6Bedrooms:
    • 6.5Baths:
    • 12Sleeps:
  • Description:
    BR1 King with en suite bathroom (shower stall), BR2 King or (2) Twin beds with en suite bathroom (shower stall), BR3 (2)...Read More
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