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: Sunday
    Pets Allowed: No
    • 6Bedrooms:
    • 3.0Baths:
    • 12Sleeps:
  • Description:
    Main House- BR#1 King down, BR#2 King and Twin up, BR#3 Twin up. Guest house- BR#1 Queen, BR#2 (2) Twins, BR#3 (2) Twins...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 6Bedrooms:
    • 7.0Baths:
    • 12Sleeps:
  • Description:
    BR1 King en suite of large walk in shower first floor, water view and flat screened TV, BR2 (2) Twin beds. Hall bathroo...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: Yes, with approval
    • 3Bedrooms:
    • 2.0Baths:
    • 7Sleeps:
  • Description:
    BR1 Queen first floor attached bathroom (tub/shower combo) with hall entrance too, BR2 Queen and Twin on second floor, B...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: No
    • 5Bedrooms:
    • 3.0Baths:
    • 14Sleeps:
  • Description:
    BR1 King Bed with Television, Private Porch and Views of the Atlantic Ocean and Farm Pond, Second Floor, BR2 Queen Bed, ...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: N/A
    Pets Allowed: No
    • 5Bedrooms:
    • 5.0Baths:
    • 10Sleeps:
  • Description:
    BR1 Queen Bed, first floor, BR2 King Bed, second floor, BR3 Double Bed, lower level, BR4 Double bed, lower level, BR5 Qu...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: 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: Saturday
    Pets Allowed: No
    • 4Bedrooms:
    • 2.5Baths:
    • 8Sleeps:
  • Description:
    BR1 King, en suite with shower stall, BR2 Queen, BR3 Double, BR4 (2)Twin beds. All bedrooms located on first floor. Hal...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 4Bedrooms:
    • 3.5Baths:
    • 10Sleeps:
  • Description:
    BR1 King with large bathroom of tub/shower, storage and double sink vanity on the first floor. BR2 Queen second floor, B...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: No
    • 4Bedrooms:
    • 2.5Baths:
    • 8Sleeps:
  • Description:
    BR1 Queen first floor, BR2 Queen first floor, shared hall bathroom of shower stall, BR3 Queen master second floor with a...Read More
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