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
    • 3Bedrooms:
    • 2.0Baths:
    • 6Sleeps:
  • Description:
    BR1 Queen, 1st floorHall bath with tub/shower, 1st floorBR2 Double, 1st floorHall bath with tub/shower, 1st floorBR3 (2)...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: No
    • 3Bedrooms:
    • 2.5Baths:
    • 6Sleeps:
  • Description:
    BR1 Queen en suite with shower stall, 2nd floorBR2 Queen, 2nd floorBR3 (2)Twin beds, 2nd floorHall bath with shower stal...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: No
    • 4Bedrooms:
    • 2.0Baths:
    • 8Sleeps:
  • Description:
    BR1 Queen, 2nd floorBR2 Double, 2nd floorBR3 Bunk beds, 2nd floorBR4 (2)Twin beds, 2nd floorHall bath with tub/shower, 2...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: No
    • 5Bedrooms:
    • 3.5Baths:
    • 13Sleeps:
  • Description:
    BR1 Queen en suite with separate tub and shower, 3rd floorBR2 Queen, 3rd floorBR3 (2)Twin beds, 3rd floorHall bath with ...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 with shower, 1st floor(BR1 step down into bedroom from hall)BR2 Queen, 2nd floorBR3 (2)Double beds, 2n...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, 1st floorBR2 Queen, 2nd floorBR3 (2)Twin beds, 2nd floor...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 4Bedrooms:
    • 2.0Baths:
    • 6Sleeps:
  • Description:
    BR1 Queen, 2nd floorBR2 Double, 2nd floorHall bath with shower only, 2nd floorBR3 Queen, 1st floorBR4 Queen, 1st floorHa...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: No
    • 4Bedrooms:
    • 3.5Baths:
    • 8Sleeps:
  • Description:
    BR1 Queen en suite with shower stall, 1st floorBR2 Queen en suite with shower stall, 2nd floorBR3 Queen, 2nd floorBR4 (2...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 en suite shower stall, 3rd floorBR2 Queen bunk beds, 1st floorBR3 (2)Twin beds, 1st floorBR4 King, first floor...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 5Bedrooms:
    • 4.0Baths:
    • 12Sleeps:
  • Description:
    BR1 King en suite with shower stall, 1st floorBR2 King en suite with tub/shower, 1st floorBR3 Queen and (2)Twin beds en ...Read More
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