Oak Bluffs: Vacation Rental By Owner

Showing 20 Of 169 Vacation Rentals
  • Property-1 Image 1
    House $164 / Nightly
    • 2 Bed
    • 2 Baths
    • (21) Excellent
    Oak Bluffs, MA

    Centrally located from nearby Vineyard Haven, Oak Bluffs, Edgartown and West Tisbury. Beaches and trails in close proximity. 5 minutes away from ferry. Upgrade... ...more

  • Property-2 Image 1
    House $1,002 / Nightly
    • 5 Bed
    • 5 Baths
    • (11)
    Oak Bluffs, MA

    Original 1900 Victorian home, updated in 2006, located in the historic Copeland District just one block from the beach. Three story home boasts decks and wrap... ...more

  • Property-3 Image 1
    House $355 / Nightly
    • 2 Bed
    • 1 Baths
    • (15) Exceptional
    Oak Bluffs, MA

    This perfect family getaway is located in a quiet neighborhood within walking distance to downtown Oak Bluffs, Circuit Ave, the Ferry, Inkwell Beach, the Vineyard... ...more

  • Property-4 Image 1
    House $780 / Nightly
    • 4 Bed
    • 3 Baths
    • (1) Exceptional
    Oak Bluffs, MA

    Recently updated this lovely 4 bedroom, 3 bath contemporary home features an open floor plan in the living and kitchen areas opening to the covered porch and... ...more

  • Property-5 Image 1
    House $395 / Nightly
    • 3 Bed
    • 3 Baths
    • (19) Excellent
    Oak Bluffs, MA

    Newly renovated home across the street from the lagoon and sailing camp! This home features, new stainless steel appliances, granite counter tops with an island.... ...more

  • Property-6 Image 1
    House $642 / Nightly
    • 5 Bed
    • 3 Baths
    • (11)
    Oak Bluffs, MA

    Welcome to "Eventide." Your historic vacation home is nestled at 63 Temahigan Ave. in Oak Bluffs- Martha's Vineyard. Conveniently situated minutes from the ferry... ...more

  • Property-7 Image 1
    House Select Dates for Price
    • 4 Bed
    • 3 Baths
    • (1) Exceptional
    Oak Bluffs, MA

    New construction property overlooking Vineyard Haven Harbor where water views can be enjoyed from almost all areas of the house. A tastefully decorated smart... ...more

  • Property-8 Image 1
    House $3,741 / Nightly
    • 4 Bed
    • 5 Baths
    • (45)
    Oak Bluffs, MA

    In a very quiet Oak Bluffs neighborhood, two miles from the Atlantic Ocean and town center. Get ready for a vacation house that every member of your family will... ...more

  • Property-9 Image 1
    House Select Dates for Price
    • 2 Bed
    • 3 Baths
    • (1) Exceptional
    Oak Bluffs, MA

    Vineyard Walk Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click "Book Now!" This... ...more

  • Property-10 Image 1
    House Select Dates for Price
    • 4 Bed
    • 3 Baths
    • (2) Excellent
    Oak Bluffs, MA

    This exquisite, shingled Colonial house with an expansive wraparound porch is synonymous with Martha's Vineyard architectural style. The 2,500-square-foot... ...more

  • Property-11 Image 1
    Studio $200 / Nightly
    • 1 Baths
    • (6) Very Good
    Oak Bluffs, MA

    Island Inn - 26F Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click "Book Now!" Make... ...more

  • Property-12 Image 1
    Townhome $299 / Nightly
    • 2 Bed
    • 2 Baths
    • (18) Excellent
    Oak Bluffs, MA

    Island Inn - 43G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click "Book Now!" You'll... ...more

  • Property-13 Image 1
    House $363 / Nightly
    • 4 Bed
    • 3 Baths
    • (27)
    Oak Bluffs, MA

    Oak Bluffs Beauty Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click "Book Now!"... ...more

  • Property-14 Image 1
    House $875 / Nightly
    • 5 Bed
    • 5 Baths
    • (13)
    Oak Bluffs, MA

    #OB Pool House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click "Book Now!" There's... ...more

  • Property-15 Image 1
    Condo $255 / Nightly
    • 1 Bed
    • 2 Baths
    • (8) Exceptional
    Oak Bluffs, MA

    Island Inn - 28G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click "Book Now!" This... ...more

  • Property-16 Image 1
    Townhome $299 / Nightly
    • 2 Bed
    • 2 Baths
    • (12) Very Good
    Oak Bluffs, MA

    Island Inn - 40G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click "Book Now!" A... ...more

  • Property-17 Image 1
    Condo $266 / Nightly
    • 1 Bed
    • 2 Baths
    • (6) Very Good
    Oak Bluffs, MA

    Island Inn - 38G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click "Book Now!" With... ...more

  • Property-18 Image 1
    House $1,015 / Nightly
    • 4 Bed
    • 2 Baths
    • (22)
    Oak Bluffs, MA

    The Walker House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click "Book Now!" Relax... ...more

  • Property-19 Image 1
    Condo $266 / Nightly
    • 1 Bed
    • 2 Baths
    • (8) Very Good
    Oak Bluffs, MA

    Island Inn - 32G Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click "Book Now!"... ...more

  • Property-20 Image 1
    Studio $200 / Nightly
    • 1 Baths
    • (11)
    Oak Bluffs, MA

    Island Inn - 24F Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click "Book Now!" You... ...more

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Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Oak Bluffs. Many accommodations in Oak Bluffs provide "Non Smoking Only", there are 276, or there are 246 of Vacation Rentals in Oak Bluffs with a "Children Welcome", there are also 221 with "Pets Not Allowed", which is another great reason to visit Oak Bluffs.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Oak Bluffs. The most expensive month of the next 12 months is in July, where prices hit an average of $398 a night. In June, prices will hit an average low of $355 per night.