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Oak Bluffs Vacation Rentals

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    Travelers to Oak Bluffs are booking June dates now. Secure your vacation rental today, and have the perfect trip.
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    3 Bedrooms, Sleeps 6Quick View
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    3 Bedrooms, Sleeps 6Quick View
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    Beautiful home in a quiet area, near all the shopping. Walk to beaches and the center of Oak Bluffs. On the bus line between Oak Bluffs and Vineyard Haven/Tisbury. Contemporary style, full kitchen, outdoor shower, deck and grill, parking. Sunny and private and feels like it's in the woods. Two...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Patio
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    This charming Cape style Oak house residence is situated on a wooded lot near bike path and just a short ride to town center and ferry. This home features an open design with a bright kitchen/dining/living area with hardwood floors, den and full bath on the first floor. Sliders in the dining area...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 3 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 9Quick View
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    Spacious gingerbread directly across from Union Chapel. Sit and watch the action roll by from the comfort of large front porch or enjoy the quiet and private yard/patio on the side of the house. Even though there are 3 parking spots on the premises the location affords you the luxury to easily walk...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    1 Review
    4 Bedrooms, Sleeps 8Quick View
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    Excellent of 5 bubbles
    Reviewed August 22, 2014
    So often descriptions fall short of reality but our stay at this Flip-key rental was as it was toted, a "Charming Farmhouse." The four bedrooms were sweet and spacious decorated...
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    About this property
    This is an old farmhouse consisting of 2 floors with 3 bedrooms on the second floor and 1 on the first floor. One queen and 3 doubles. A large living room and bath on the first floor. In the kitchen is a Refrigerator, gas stove with oven, a washer and dryer and a dishwasher. There is a portable...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8Quick View
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    • Balcony
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    About this property
    New Renovated, 1870 historic "Campground" cottage centrally located in Oak Bluffs, The cottage has 4 bedrooms (all located on the second floor) - 1 queen, 2 double beds and 2 twins beds. The front bedroom has its own balcony with water views. Cottage sleeps 8. the first floor includes a newly...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    • Balcony
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    • Terrace
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Adorable GINGER BREAD house in Oak Bluffs that I rent out for 6 weeks each summer. Best location! It's a 2 minute walk to the harbor, town restaurants, shops and bars. The OCEAN is a 6 minute walk! House is adorable, furnished, AC in some rooms, parking. Overlooking a park, sip your coffee on the...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, Sleeps 8Quick View
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    • Central Heating
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    Pet friendly
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 9Quick View
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    • Satellite TV
    • Balcony
    • Porch
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    Pet friendly
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    About this property
    JUNE & JULY RATES REDUCED!!<BR><BR>You will be within walking distance from downtown shopping, movie theatre, restaurants, bike path, harbor, beaches, and two-tenths of a mile from the brand-new modern library.<BR><BR>Relaxed and warm, this brand-new home is expertly decorated. The open floor plan...
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    • Grill
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    • Terrace
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    Pet friendly
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    • Balcony
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, Sleeps 4Quick View
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, Sleeps 8Quick View
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Oak Bluffs, Martha's Vineyard 02536
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 13
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    • Private Outdoor Pool (Unheated)
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 22
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 9
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, Sleeps 10Quick View
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 9Quick View
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    2 Bedrooms, Sleeps 7Quick View
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    6 Bedrooms, Sleeps 10Quick View
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8Quick View
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    6 Bedrooms, Sleeps 10Quick View
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    About this property
    *Fall/Winter/Spring multi-week discount available *Only 1 prime summer week left! Check my calendar and book ASAP if you plan to visit in the peak season. *Perfect location so No Car Needed. Easy walk to town, beach & parks. The Pennacook house in Oak Bluffs on the charming island of Martha's...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 7Quick View
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    • Outdoor Dining Area
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    About this property
    A comfortable ranch with all the amenities for a perfect vacation. It's quiet location is 1.5 miles from town, yet not too far to bike or walk in when needed. Beaches, ponds, the lagoon, and other recreational facilities are also easily accessible if you want to hop on the bike path around the...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Oak Bluffs, Martha's Vineyard 02568
    Rental Home - 1 Bedroom, 3 Bathrooms, Sleeps 4
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    4 Bedrooms, Sleeps 8Quick View
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 10Quick View
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Amenities & Details
    • Patio
    • DVD Player
    • Internet Access
    • Parking
    • Washer
    • Grill
    • Satellite TV
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Oak Bluffs, Martha's Vineyard 06557
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 8
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    67° 49°
    June
    72° 53°
    July
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