Oak Bluffs Vacation Rentals

One of the island’s most popular destinations, Oak Bluffs offers a broad range of attractions for kids and adults, from ice cream parlors and an arcade to the dozens of shops, restaurants, and bars along and around Circuit Avenue. The town hosts annual special events, including late-summer fireworks at Ocean Park and Illumination Night, when Campground residents put thousands of unique and colorful Chinese lanterns on display. 

You can also view all of our Martha's Vineyard Vacation Rentals.  Or search for rentals in EdgartownEdgartown VillageKatamaChilmarkVineyard Haven Tisbury, or West Tisbury.

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  • Property Highlights
    Unit Code: OB CMAT-400
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:6
    • Bath:5.5
    • Sleeps:12
  • Description:
    Tucked back up a hill overlooking Lagoon Pond, this architect-designed Modern Gem enjoys grand indoor-outdoor living... Read More
  • Property Highlights
    Unit Code: OB BFLO-48
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:6
    • Bath:9.5
    • Sleeps:16
  • Description:
    This deluxe compound at The Preserve makes a grand multi-generation or larger group Vineyard getaway destination. There... Read More
  • Property Highlights
    Unit Code: OB VBUT-09
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:9
    • Bath:5.5
    • Sleeps:18
  • Description:
    NEW FOR SUMMER 2024 - This water view Compound with a recently renovated six-Bedroom Main House and a brand new... Read More
  • Property Highlights
    Unit Code: OB PMOR-12
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath:6.5
    • Sleeps:8
  • Description:
    This luxurious home at The Preserve is designed for indoor-outdoor living, with modern styling throughout its deluxe... Read More
  • Property Highlights
    Unit Code: OB MCAL-28
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:6
    • Bath:8.0
    • Sleeps:12
  • Description:
    This newly constructed Modern Farmhouse at The Preserve is designed for the ultimate indoor-outdoor living experience... Read More
  • Property Highlights
    Unit Code: OB LSMA-06
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:5
    • Bath:7.0
    • Sleeps:10
  • Description:
    This grand five-bedroom Compound at The Preserve has luxurious detailing and styling throughout, including an attached... Read More

discount tag Last-Minute Deals


Looking for a last-minute getaway to Martha's Vineyard this summer for July or August? We've got some great homes and some great deals. With car ferry reservations now sold out for all weekends, we have some creative alternatives that will still get you to the Vineyard this summer! We have homes that: include transferable car ferry tickets; others with very flexible check-in days; and some, even with a car rental credit available. Please call us to explore your options 508.939.9422

Grand Coastal-Style Estate In The Preserve With Pool And Hot Tub $10,000 - $30,000/week

  • Property Highlights
    Unit Code: OB RSMI-16
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:5
    • Bath:6.5
    • Sleeps:12
  • Description:
    POINT B EXCLUSIVE - *Special Offer: Save up to $4,000/week On Available July + August Weeks* (new rates programmed). ... Read More

Luxury Gambrel With Pool At The Preserve $18,000 - $28,500 Per Week

  • Property Highlights
    Unit Code: OB CPOU-38
    Pets Considered: Yes
    Town/Area: Oak Bluffs
    • Bedrooms:5
    • Bath:5.5
    • Sleeps:10
  • Description:
    Enjoy deluxe vacation living in The Preserve at this luxurious Gambrel with pool. There are three levels of living space... Read More
  • Property Highlights
    Unit Code: OB VMOS-02
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:8
    • Bath:4.0
    • Sleeps:18
  • Description:
    Villa Rosa is one of the most prominent Victorian mansions in Oak Bluffs — known as much for its grandeur and... Read More
  • Property Highlights
    Unit Code: OB LPER-385
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath:4.5
    • Sleeps:10
  • Description:
    This waterfront home features three levels of striking indoor living space, nicely integrated with outdoor living spaces... Read More
  • Property Highlights
    Unit Code: OB NHOL-55
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath:5.5
    • Sleeps:10
  • Description:
    This grand Ocean Park Victorian has been meticulously restored to her resplendent grandeur, maintaining the original... Read More
  • Property Highlights
    Unit Code: OB CTAY-10
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:5
    • Bath:4.5
    • Sleeps:10
  • Description:
    This luxurious compound is tucked away in the desirable new enclave The Preserve. It features deluxe styling throughout... Read More