Oak Bluffs Rentals


Our Oak Bluffs rentals are the prime summer vacation destination in 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 Bluff vacation rentals, visit the town center,  located on the harbor and has 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: 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: Sunday
    Pets Allowed: No
    • 3Bedrooms:
    • 2.0Baths:
    • 6Sleeps:
  • Description:
    Main Level: BR1 Queen main level, BR2 (2) Twins main level, Hall bathroom (tub/shower). Lower level: kitchen, dining are...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 4Bedrooms:
    • 2.5Baths:
    • 8Sleeps:
  • Description:
    BR#1 Queen first floor, BR#2 Queen first floor, BR#3 King first floor w/ full bath, BR#4 (3) Twins second floor. The A/C...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: Yes, with approval
    • 4Bedrooms:
    • 3.0Baths:
    • 10Sleeps:
  • Description:
    BR1 Queen Master with en suite bathroom shower only second floor, BR2 Queen Bunk Beds lower level, BR3 (2) Twins lower l...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Friday
    Pets Allowed: No
    • 3Bedrooms:
    • 1.5Baths:
    • 6Sleeps:
  • Description:
    All bedrooms on the lower level level BR1 Queen, BR2 Double, BR3 (2) Twin beds with hall bathroom of tub and shower. Was...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: N/A
    Pets Allowed: No
    • 3Bedrooms:
    • 3.5Baths:
    • 6Sleeps:
  • Description:
    BR1 King en suite with walk in shower, second floor, BR2 Two twins en suite with shower stall, second floor, BR3 Queen s...Read More
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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
    • 5Bedrooms:
    • 2.5Baths:
    • 11Sleeps:
  • Description:
    BR1 King second floor with private bath of tub and shower, BR#2 King second floor, BR3 Queen second floor, BR4 Double s...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 3Bedrooms:
    • 1.0Baths:
    • 8Sleeps:
  • Description:
    ...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: Yes, with approval
    • 3Bedrooms:
    • 4.5Baths:
    • 8Sleeps:
  • Description:
    BR1 King Bedroom with en suite bathroom on first floor, BR2 Queen Bedroom with en suite bathroom second floor, BR3 Quee...Read More
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