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Oak Bluffs Vacation Homes

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    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Architect designed, luxury waterfront retreat. This unique home sits overlooking 500 feet of private lagoon beach and maintains sweeping waterviews up the lagoon. The pool and patio areas feature outdoor dining, sectional sofa seating, lounge area, and a hot tub all taking full advantage of the... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Leave your worries and your car behind, this picture perfect Vineyard beach house is steps from downtown Oak Bluffs, the sandy beach and a few short blocks from the ferry. Recently renovated and restored, four-bedrooms and one and a half baths, offering the perfect juxtaposition of cottage charm... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Classic vineyard cottage renovated, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. Main living level features a lovely kitchen very well stocked with dining and cook items, a large sunporch living area and 2nd living area with large screen TV. Three lovely... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Large families looking for a beachfront adventure will love this relaxed waterfront home. Spectacular views from every room and expansive patios stretch the shoreline. Central location offers a 5 minute drive to town, dining, movies, shops and galleries. Amenities and Features include...... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Walk to town and beach from this spacious modern home on a beautiful, treed lot. A delightful blend of amenities and charm. Central air conditioning. Amenities and Features include... Walk to Town, Central Air, WiFi Additional amenities include: beach chairs, coffee maker, patio table and... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Spectacular water view in desirable East Chop neighborhood. This 4 bedroom, 3 bath home is just 1.5 miles from Oak Bluffs Center and Beach. There is a yard with multiple decks and waterviews. Features include central air and wifi internet. Beautifully decorated. Amenities and Features include...... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    10 minute walk to Oak Bluffs center and beach area from this lovely modern vacation home. Enjoy all that the summer community of Oak Bluffs has to offer, quaint shops, fine and family dining, harbor front stroll where you will and array of dining establishments, all waterside, boat rentals and... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
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    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Sea Glass Cottage Martha's Vineyard Vacation Rentals Sleeps 6. Completely renovated, this charming East Chop cottage will allow its guests to experience all the comforts of modern luxury living combined with the historical splendor of many reclaimed antique furniture pieces from Martha's Vineyard... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 25
    5 of 5 bubbles (1) Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Located on over 1 acre of waterfront property on East Chop, an exclusive area of historic Oak Bluffs, this unique home is perfect for family and friends that want to vacation together while allowing for separation. This home can accommodate up to 12 people. No longer need to rent multiple homes on... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 of 5 bubbles (2) Very good
    8 Bedrooms, 3 Bathrooms, Sleeps 16 | Quick View
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    About this property
    A true Vineyard classic from 1890, this house retains its authentic charm yet has been thoughtfully renovated and serves the modern day vacationer well. The 8 bedrooms afford plenty of space to accomodate larger family groups for special reunions and vacations. The living room, sunporch and kitchen... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    Gracious 5 bedroom in-town victorian offers easy access to shopping, ferry, park with basketball and tennis and beach. This home has been lovingly maintained and restored to it's prior elegance. Enjoy cocktails on the beautiful three season porch. Additional amenities include: coffee maker,... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This unique and elegant four bedroom beach cottage is situated on the north shore of Martha's Vineyard. For your relaxation, there is a large porch/patio leading out to the beach affording magnificent views. Additional views from the tastefully decorated living area, bedrooms areas, make this a... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beautiful, spacious, 4 bedroom 3.5 bath contemporary home set in a quiet lovely community on the outskirts of Oak Bluffs. This home comfortably hosts extended families with multiple living spaces. The main living level features an open concept and hosts a family TV room and luncheon breakfast nook,... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
    1 / 22
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    Classic, "Camp Ground" over sized 7 bedroom 3 bath home in a residential neighborhood within easy walking distance to the beach, shops, restaurants, galleries, etc. It offers double master bedrooms (1st and 2nd floor.) Enjoy rocking on our huge front porch in over sized Georgia rockers. As you... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This lovely 3 bedroom home features an open floor plan on the living level, colorful decor, window ac in all rooms and a well equipped modern kitchen. The home is nicely situated in quiet neighborhood, on the outskirts of Oak Bluffs, convenient to all three down island towns and beaches and a short... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Air conditioning has been added for the 2017 season! Waterview Farm is a private association with wonderful meadow and water views. It is adjacent to Farm Neck Golf and Tennis Club, which is open the public. There is access to Sengekontacket Pond to launch canoes and kayaks from the private... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Beautiful four bedroom home within walking distance to the Oak Bluffs harbor and town. This home has a nice size first floor living room and separate eat in kitchen. The first floor also has a full bathroom with tub and shower. The second floor has four bedrooms and one full size bathroom. The... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    1 / 23
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Views, Views and more Views! Lovely water views of Sengekontacket Pond over the rolling "forever" conservation land. Large contemporary home has been recently updated to 4 bedrooms and 3 full baths. Large open living space with deck overlooking the view and sun room. Access to association dock and... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Four bedroom Oak Bluffs home located in the Waterview Farm area of Oak Bluffs. Adjacent to Farm Neck Golf & Tennis. Access to Sengekontacket pond. Great for kayaking and canoeing. Large house great for an extended family or two small families. The first floor has an open concept living room,... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Wonderful Oak Bluffs home close to town and beach. This home has an open floor plan which is nice for relaxing with family and friends. Also enjoy the screened porch off the living area. Additional amenities include: coffee maker, outdoor shower, cd player, wine glasses, washer & dryer, ironing... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Immaculate, waterview town house located in the desirable Sengekontacket Pond area of Oak Bluffs. Wonderful waterviews of Sengkontacket Pond and Nantucket Sound. This spacious unit offers a bright open airy feeling with three levels of living area. The main floor includes bedroom, living, dining... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Newly renovated and painted campground Victorian home with gingerbread accents. This charming Victorian is ideally located close to town, shops, restaurants and beaches. Enjoy peeks of the harbor while watching the sunset from the new roof top deck. Additional amenities include: coffee maker,... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 20
    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Wonderful home located about a 10 minute walk to downtown Oak Bluffs. This home has a nice open floor plan for family gatherings, updated furnishings, fully equipped kitchen with stainless steel appliances, Master bath Jacuzzi tub, Entertainment systems include flat screen TVs, CD, DVD, VCR,... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Beautiful waterfront home with central A/C, features open floor plan and sunny living spaces. The great room has two distinct seating areas and is equipped with a flat screen TV. There is a formal dining room set between the living area and kitchen and opens to the outdoor patio with gorgeous... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This is a wonderful vacation house located about a 10 minute walk to town and little further to the town beach. The home was recently renovated and has a nice open floor plan on the main level which has an updated kitchen, family room and dining space. There is also a bedroom and full bathroom on... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Wonderful, spacious, lovingly maintained and attractive home in exclusive setting - family room with fireplace, large formal living room with fireplace, master bedroom with full private bath. Large kitchen and dining area that opens onto wonderful deck. Association tennis and boat landing on... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Little Jaws, the home where the movie Jaws was filmed is a pristine beach cottage. Set in East Chop, this three plus bedroom rental offering features spectacular views, great swimming, kayaking and gorgeous sunsets. Relax on the large and comfortably furnished waterfront veranda. The living room... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
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    4 Bedrooms, 5 Bathrooms, Sleeps 6 | Quick View
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    This grand Victorian jewel on Ocean Park has been completely renovated and transformed into a beautiful vacation home. Enjoy water and park views from inside this elegant home, the expansive wraparound porch and the second floor balcony. This beautifully restored Victorian home is a rare find... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This charming home sits atop the Lagoon bluffs w/stairs down to a narrow private beach It offers waterviews from many rooms (including a wonderful glassed in/screened porch). The living room sports bay windows to access the view, and there's a studio w/a private entrance and kitchenette. Outside is... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Set in one of the Island's loveliest planned residential areas with beautiful landscaping, overlooking Sengekontacket Pond. Wonderful pond views from all bedrooms and living area. This spacious three floor house is well maintained and attractively decorated. Full deck across back facing pond.... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Sitting on the "summer porch" (that is what they were called in the days of old) sipping your favorite beverage, strolling the short distant to the water, relaxing around the table, Well equipped kitchen, reading in the living room with your feet these are possible when you stay in this well cared... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Completely renovated cottage in the Sunset Lake area of Oak Bluffs. Walk to town and library. Completely renovated modern kitchen. Rock away on the large front porch. Additional amenities include: games, coffee maker, outdoor shower, lobster pot, cd player, wine glasses, fans, vacuum, washer &... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
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    7 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Come and relax on the front porch of this lovely Vineyard home. Located in the desirable East Chop area of Oak Bluffs. The first floor has a nice open space with dining area and living room. There is a nice kitchen with everything you need to make family dinners. There is a bedroom and full... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Spacious contemporary 4 bedroom 3.5 bath home located in one Oak Bluffs most exclusive neighborhoods. This house offers many features such as hardwood floors, central air conditioning, and a large living dining area with walk out deck and patio. The yard is nicely landscaped with waterviews over... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This cozy, quaint waterfront property offers beautiful sunsets and great harbor views. Swimming, boating, kayaking, are just steps from this warm and charming quintessential Vineyard cottage. Amenities and Features include... Waterfront, Waterview Additional amenities include: dock/boat-slip,... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Luxury waterfront home with dock, deep water mooring, a private beach as well as deep water access and marina facilities close-by. Enjoy a commanding view of Lagoon Pond with gorgeous westerly sunsets - second to none! This home offers a spacious open floor plan providing a comfortable yet elegant... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
    • Satellite TV
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    • Pet-friendly
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    • x
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    About this property
    Sweet three bedroom gingerbread house right in the heart of downtown Oak Bluffs. Walking distance to Ink Well Beach, shopping and ferry. Lovely front porch and back deck complete with outside shower! This quaint cottage is perfect for your relaxed summer getaway! Additional amenities include:... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
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    5 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Grill
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Beautiful luxury home overlooking Farm Neck Golf Course and Sengekontacket Pond. Large family living spaces include a great room with soaring ceilings opening to the patio as well as a large TV/family room. Expansive gourmet kitchen with dining area is great for family gatherings after the beach.... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Grill
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    • Shared Outdoor Pool...
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    • x
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    • x
    About this property
    Welcome to "Shangrila" A beautiful townhouse condominium end unit with magnificient views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Satellite TV
    • Grill
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    This home is Oak Bluffs at its best - close to town but tucked away off a main street, the house is truly a beauty with special, thoughtful details and wonderful furnishings. The new home has the yummiest colors with a handsome, soft blue master bedroom and bath, a twin bedroom in warm gold, one... View all property information
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    Oak Bluffs, Martha's Vineyard
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
    • Grill
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    • Internet Access
    • Porch
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    • Patio
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    A fully renovated four bedroom home with 3 1/2 baths, family room, landscaped lot and a private beach and dock. Dock can accommodate up to a 25 foot motor boat, located on The Lagoon and is accessible to Vineyard Sound. Family room has cable TV, deck, fully equipped kitchen, and a 2 person kayak... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • x
    About this property
    Great Getaway Cottage with a short walk to Circuit Ave, the harbor, and the Lagoon .A back yard w/ picnic table, BBQ grill. About a mile walk or bike ride to Town. The house has hardwood and fir floors throughout and also has air conditioning. This is a great "get away cottage" for a small family... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 10
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Private Garden
    • Wi-Fi
    • Satellite TV
    • Secure Parking
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful, spacious, 6 bedroom 4 full, 2 half baths set in a quiet and private area of Oak Bluffs, close to Edgartown, Vineyard Haven, area beaches and attractions. This home comfortably hosts extended families with multiple living spaces. The main living level features 2 master bedrooms (one... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
    • Air Conditioning
    • Internet Access
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Pristine clean cottage just on the outskirts of Oak Bluffs , Bike or drive to village center. The home features light filled living and dining area with oversize windows, large kitchen, two bedrooms each with window ac and one bath. There is a large screened in porch where guests can relax and... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557