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Oak Bluffs House Rentals

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    Travellers to Oak Bluffs are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    188 Matching Rentals in Oak BluffsView all 217 rentals
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    Charming 3br Getaway in Oak Bluffs1 / 22
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Oak Bluffs Contemporary Summer Home1 / 18
    (5)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Located just on the outskirts of Oak Bluffs and overlooking the lagoon this sweet summer home offers walking access to the lagoon for morning swims and is a great area for kayak enthusiasts. The sun filled interior features open living kitchen and dining area with a wall of glass that opens...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Lovely Summer Home located in Waterview Farms a private community on the outskirts of Oak Bluffs ******* Sengekontacket Pond, ( saltwater in inlet from the North Shore). This special home boasts beautiful views across peaceful meadows to Sengekontacket Pond and the North Shore beyond. Launch...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Waterfront, Seaview Condo # 205 is a corner unit with balcony, spectacular waterviews and has been all newly updated for 2017 season. Perfect in town location just across the street from Inkwell Beach, walk to town center or pick up the bike path just a few hundred yards from the complex and bike...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Gracious home features an open, airy floor plan. The large living area with all glass walls opens to a large private deck. Patio furnishings and dining table provide additional space for relaxing and barbecues. Spacious modern kitchen is equipped with all modern amenities. This lovely home is...
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    Oak Bluffs, Martha's Vineyard 02536
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    If you are looking for an immaculate, charming, cottage style, yet modern home and close to Oak Bluffs center look no further. This recently updated 3 bedroom, 2 bath home features sunny open living, kitchen and dining areas. Soft seashore color palette throughout adds to the ambiance of this...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Spacious tri-level contemporary home in the desirable Oak Bluffs community of Meadow View Farms. Conveniently located close to downtown Oak Bluffs with easy access to both Vineyard Haven and Edgartown, This home sits at the edge of a multi-acre conservation area with bountiful trees surrounding...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Spacious and attractive waterfront Cape Cod style home - features gorgeous views, central A/C, Wi-Fi and 4 TV's. Two large decks and a screened porch provide wonderful spaces for summer relaxation in which to enjoy the waterviews. Kayaking enthusiasts will enjoy the gorgeous scenery and wild life...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    About this property
    Bright and newly remodeled classic summer cottage. Conveniently located just one mile from Oak Bluffs town center, Ink Well Beach, shops, fine and family dining, historic Flying Horses Carousel, public tennis courts, Bandstand Park and Oak Bluffs Harbor-front area. The professionally landscaped...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    All newly remodeled and furnished and tucked away on a quiet Oak Bluffs lane for the perfect reprieve after a day at the beach and shopping in town, along the Oak Bluffs harbor - and all just a short drive or bike ride away. This vacation home looks and feels so comfortable when you first walk...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Adorable Waterfront and Beachfront cottage. Immaculately maintained, lots of summer charm, fantastic views of the Vineyard Sound and Lagoon from the large patio area. Stairs lead directly to private, sandy beach, great area for young children and adults. Kayak enthusiasts will enjoy this...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    This charming recently renovated waterfront home atop the lagoon bluffs boasts spectacular sunsets and panoramic waterfront views of the Lagoon, outer Vineyard Haven Harbor and Cape Cod from patios, living room, dining room and two upstairs bedrooms. Stairs down to private beach. \n Amenities and...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Outstanding vacation home, centrally located to all three down island town centers and multiple public beaches. Set in the Iron Hill Farm Community of homes this lovely home overlooks picturesque,- Little Duarte pond. Extended families will enjoy the multiple living spaces, 4 large bedrooms,- 3...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Stylish Cape located close to town and beach.attention to detail in every room. Relax and enjoy all the comforts of home in this all new pristine 3 bedroom, 2 bath home. The main living level features an open kitchen living and dining with AC. In additon there is separate TV room with office area...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Summer Dream offers the opportunity for a relaxing vacation in a beautiful environment. This 4 bedroom, 2 ½ bath home has a beautiful new kitchen and new living room furnishings including a 56' LED television. Summer Dream is in the lovely Hidden Cove neighborhood adjacent to Sengekontacket Pond...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    About this property
    Visitors will enjoy this delightful and comfortable four bedroom, 3 bath home in the desirable East Chop area of Oak Bluffs. Relax in the breeze with your morning coffee on the front porch and have afternoon drinks on the back patio. Several gathering areas with beautiful new furniture make...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Penacook 5 Bedroom Cottage - short stroll down one of the nicest streets in Oak Bluffs to the beach in one direction and town center in the other, where you will find shops, eateries,- gourmet and family style, entertainment, the historic Flying Horsed Carousel, and the beautiful harborfront area....
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 5 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Extended families are sure to enjoy this Tri-level home featuring open floor plan on the main level, large main living room and two den TV areas one on the first level one and an additional TV area on the 2nd level. Kitchen has stainless appliance and granite counters and the family dining area...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Escape to the perfect island getaway at this gorgeous, recently renovated Oak Bluffs home on lovely Martha's Vineyard. Light-filled bedrooms, a playroom, and a huge deck await! Downtown Oak Bluffs is nearby and it's only one mile to the water. If you'd rather remain on the property, you're...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    7 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    About this property
    Large families looking for a true shore experience will enjoy this delightful,whimsical, large historic summer home with cottage details set on the edge of Harthaven Harbor. The home boasts spectacular views of Vineyard Sound from all areas of the home. Private path leads you to a pristine...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 14
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Families are sure to enjoy this cozy home with nautical inspired decor. The main living level offers a spacious living and dining area with cathedral ceiling cooled by window AC. and a neat well equipped kitchen with pass through window. The kitchen opens onto a spacious deck with patio dining...
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    Oak Bluffs, Martha's Vineyard 02536
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    About this property
    Classic Vineyard Oak Bluffs Cottage, 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, main living room with TV and a large sunporch living area. Three lovely...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    European-styled cottage is tucked away down a private lane surrounded by private yard with gardens - you’ll feel like you have completely gotten away from it all. The front door opens into a classic Mudroom with an antique wood, stadium bench seat - and then you step into the open and airy Great...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Picturesque ocean views across Farm Pond to Vineyard Sound. Walk to beach and town. Bike path is one block away from this beautifully renovated three bedroom, two bathroom home. Open, airy with lots of glass. The dining and living areas open to deck. \n Amenities and Features include...\n \nFarm...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Open, airy contemporary Cape. All newly furnished, three bedrooms, 2 bathrooms. Ceiling fans in all bedrooms. A short 15 minute walk to Oak Bluffs Center and Beach, shopping, and dining. Sidewalks connect to miles of bike paths. \n Amenities and Features include...\n \nWalk to Town. Hi Speed...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Welcome to this wonderful and pristine clean three bedroom 2 bath Cape Style. Centrally located with easy access to town centers and public beaches all within a 15 min drive from the house. Biking enthusiasts will enjoy the easy access to bike trails that lead to both towns and many miles of bike...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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. \n Amenities and Features include...\n \nWalk to Town, Central Air, WiFi
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    BURBS - Stylish New Home, Central AC, Wifi, Screened Porch1 / 19
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Reviewed 28 July 2014
    Arrived a little early, was able to get keys right away. Lisa, was extremely pleasant to work with. The house was more than I could hope for, just immaculate. The layout was...
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    About this property
    Lovely spacious 3+ bedroom, 3.5 bedroom home within a mile from Oak Bluffs Center and beach area. Fully furnished screen porch. This home has been tastefully furnished throughout and will sleep families of 9 comfortably. \n Amenities and Features include...\n \nStylish New Home, Central AC,...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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 seating area on the front of the house and the deck and patio dining area off the back of the house. The main living room is centered around...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Custom built with extraordinary attention to detail. Located on Lagoon Pond with panoramic views up the lagoon. Large comfortably furnished deck and screened porch with dining create a most relaxing atmosphere overlooking the water. Luxury features throughout the house not seen in most rental...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    MVVR EXCLUSIVE: Adorable, pristine beach cottage has spectacular views across the sound, calm water swimming, great area for kayaking. The open kitchen, dining and living areas are enhanced by the wall of windows facing the waterfront and providing gorgeous water views . Enjoy the parade of...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 4
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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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Adorable waterfront cottage, pristinely maintained throughout the years. Enjoy privacy and views from the spacious deck. 3 minute walk to great sandy lagoon beach - a perfect place for young children to play. Centrally located just 2 miles to either Vineyard Haven or Oak Bluffs town centers....
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Smoking allowed
    About this property
    Quintessential waterfront home, situated on the north shore of Martha's Vineyard, East Chop Area. Gorgeous cottage vernacular, pristinely maintained and decorated with perfect blend of coastal colors. Private dock and mooring, for those who might wish to bring a boat, dock can accommodate a large...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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. \n Amenities and Features...
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    Location Information
    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
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    • Cable/satellite TV
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming Gingerbread Cottage located in the Tabernacle area of Oak Bluffs. A short stroll brings you to Oak Bluffs Center with shops, family and fine dining, harbor area, bandstand park, and Ink Well Beach. Recently updated, this house features a modern eat in kitchen opening to the back deck...
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    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Patio
    • DVD Player
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Meadow View Farms home, bordered by expansive landscaped yard, peaceful private setting. Association tennis courts just a short distance from the house and Farm Neck Golf and Tennis is just a half mile from the house. Miles of connecting bike paths begin at the entrance to this lovely...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Seaside Cottage Style Vacation Home. Recently renovated. Perfect for extended families. Walk to Oak Bluffs town center, beach across the street and miles of beach side - bike paths begin just a couple of hundred yards from the house. Ocean views from just about all rooms. Wonderful, large...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pristine 4 bedroom waterfront hideaway. Enjoy spectacular views and sunsets across the lagoon. Private dock for boat enthusiasts. Kayak and boat rentals can be delivered to the property and kayaking on the lagoon is a fun and picturesque activity for the entire family. Centrally located, you...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    \n Amenities and Features include...\n \nMeadow View Farms, Out of Town, Association Tennis, Hi Speed Internet
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2010 newly renovated, features central AC, all new kitchen, 2 new baths and hardwood floors on the living level. Open kitchen, living and dining areas are flooded with light from the floor to ceiling windows and opens to a large wrap around deck with lovely views of the the lagoon. The master...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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: Close to Town, Coffee...
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    Oak Bluffs, Martha's Vineyard 02539
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Set in a quiet community of homes just on the outskirts of OB, this outstanding home provides a peaceful get away yet is just a short drive to town center. The use of coastal colors and upscale furnishings throughout combine to make this gorgeous Oak Bluffs summer home a cut a above. Expansive...
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    Oak Bluffs, Martha's Vineyard 02536
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated on quiet side street with a 15 minute walk or a 5 minute drive to town and beach, this light filled cape offers visiting families a well equipped vacation reprieve featuring comfortable living areas with mini split A/C and a modern spacious kitchen The first level features an open floor...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Grill
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This outstanding Oak Bluffs home is undergoing a complete face lift for the 2012 rental season and is sure to please. Spacious and perfect for extended families, featuring multiple attractively furnished living areas and sleeping 13 comfortably. The lower level of the house features a queen bed,...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 13
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