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
    • 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: 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: Saturday
    Pets Allowed: No
    • 3Bedrooms:
    • 3.5Baths:
    • 6Sleeps:
  • Description:
    BR1 King master en suite of large walk in shower, soaking tub, double sinks and separate toilet area, BR2 (2) Twin beds,...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Sunday
    Pets Allowed: No
    • 3Bedrooms:
    • 2.5Baths:
    • 7Sleeps:
  • Description:
    BR1 Queen en suite of tub and shower first floor, BR2 (2) Twin beds second floor, BR3 Queen and (1) Twin second floor, s...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: 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:
    • 4.5Baths:
    • 11Sleeps:
  • Description:
    BR#1 Queen first floor with private bathroom of tub and shower. BR#2 Queen first floor attached to the house with a priv...Read More
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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 separate tub and walk in shower main floor - extra wide doors within this room for handicapped acce...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 3Bedrooms:
    • 3.0Baths:
    • 8Sleeps:
  • Description:
    BR1 A set of twin bunk beds and a twin trundle bed with a twin in the drawer which stays low when pulled out, first floo...Read More
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  • Property Highlights
    Area: Oak Bluffs
    Turnover Day: Saturday
    Pets Allowed: No
    • 4Bedrooms:
    • 3.0Baths:
    • 8Sleeps:
  • Description:
    BR1 Queen with a hall bathroom of shower stall just across from it, BR2 King en suite of tub and shower, BR3 Queen, BR4 ...Read More
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