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Holiday Rentals and Homes in Oak Bluffs, MA

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    280 Holiday Rentals in Oak Bluffs
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    €3,292
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    1 / 15
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    €927
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    4 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    €1,437
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    €788
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    1 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    'About Time' .......Treat your wallet to a vacation. Come to SECOND AVE; Quiet neighborhood, Great outdoor space. A/C Neat clean and tidy. Sleeps five. Walk to town, beach, and all that historic Oak Bluffs has to offer. A great value! First floor has the living room with flat screen TV and sleep... View all property information
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    €1,484
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    • Waterfront
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    About this property
    This charming home is situated in an idyllic private wooded setting on Sengekontacket Pond, one of the largest salt-water ponds on Martha's Vineyard. Comfortably furnished, it has a newlyr renovated kitchen and a new dining area overlooking Major's Cove. There is also a new screened in sun room for... View all property information
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    €3,246
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    1 / 23
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This classic New England-style shingle home has a modern coastal-look throughout, and is conveniently tucked away in the Sunset Lake area of Oak Bluffs, with easy access to all of downtown, plus use of a private tennis court. The first floor features a bright, open Living Area with fireplace and... View all property information
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    €3,524
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    About this property
    Spacious sun filled contemporary home located on a quiet private street,a 10 minute walk to town center, Inkwell Beach and harborfront, The first level features a spacious kitchen with stainless steel appliances, prep counter with range top. and breakfast nook, there is a comfortable living area... View all property information
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    €1,484
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    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Beautiful three bedroom two and a half bath home located in Oak Bluffs. Walking distance from the lagoon and beach. Close proximity to downtown Oak Bluffs and the beaches. Large backyard and deck and finished basement. Queen sofa bed in basement. Additional amenities include: beach chairs,... View all property information
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    €2,689
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    1 / 16
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    About this property
    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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    €4,405
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    About this property
    In Town, walk to beach, tennis and town area. This wonderful family home has a large wrap around porch, 7 bedrooms and sleeps 12-14. Many areas of this wonderful older home have been updated. Hi Speed Internet. Amenities and Features include... 1 Block to Beach, Wifi Internet, Linens Provided,... View all property information
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    €278
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    1 / 5
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    This 3.5 bedroom home with skylights, 52 inch Tv, computer, internet, printer, fax, is your home away from home. 1 mile from town 1.5 mile from beach and 7 miles from airport is ideal location. 2 SETS OF GOLF CLUBS AND 4 TENNIS RACQUETS FOR YOUR USE, 3 CABLE TV'S, MASTER BATH HAS WHIRLPOOL TUB... View all property information
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    €2,504
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    1 / 23
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Spacious and pristine four bedroom contemporary located in lovely private down-island community. All new decor, air conditioning, association tennis courts and bike paths. Views from spacious deck across professionally landscaped yard to Sengekontacket Pond. Amenities and Features include...... View all property information
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    €1,530
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    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 are... View all property information
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    €291
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    About this property
    Renovated beach house in Oak Bluffs with 5 Bedrooms, 2 full baths, Sleeps 8; Large living/dining room, sliding door opens to deck, flagstone picnic area with gas grill, A/C, Washer/Dryer, Free WIFI, Large flat-screen LED TV's with cable service; Located 10-20 min walk to Oak Bluffs harbor, beach... View all property information
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    €2,689
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    1 / 17
    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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    €198
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    1 / 20
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Great Getaway Cottage with a short walk to town, the harbor, and the Lagoon .A back yard picnic table, BBQ grill, and swing set. 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... View all property information
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    €1,298
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    About this property
    Adorable and immaculate three bedroom, two bath cottage located just 1.5 miles from Oak Bluffs center and town beach area. Bike paths located at the end of the street for touring or access to town. Less that a half mile to Farm Neck golf course, tennis and dining. House features all amenities... View all property information
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    €2,133
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    1 / 13
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    OAK BLUFFS, Meadow View Farms: Contemporary salt box with open floor plan. Easy access to the bike path, Farm Neck for golf, and three miles to village center and the beach. Large deck overlooks the landscaped yard Additional amenities include: living room, tennis: assoc., dining cap: 8,... View all property information
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    €2,504
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    About this property
    Lovely two bedroom, 2 bath condo unit with sweeping water views. Town center is but a 5 minute walk from the condo complex where you will find, family and fine dining, shops. groceries, the famous Flying Horse Carousel,- a great attraction for children and the young at heart. Stroll along the... View all property information
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    €3,339
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    About this property
    MVVR EXCLUSIVE: Relax and enjoy an island experience from your private beach with views across the Vineyard Sound to Wood's Hole. This beach house features a casual, open decor with 4 bedrooms and 2-1/2 baths. Close to all activities. Amenities and Features include... Waterfront, Beachfront,... View all property information
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    €6,956
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    About this property
    Historic harborfront home with private dock has been completely renovated and newly furnished, beautifully appointed throughout to reflect summer living on the Vineyard. The large living and dining areas open onto the expansive and comfortably furnished porch, overlooking picturesque Oak Bluffs... View all property information
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    €5,843
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    About this property
    East Chop Waterfront. Recently renovated 5 bedroom, 5 bath home. Extraordinary views from the interior and multiple decks for relaxing overlooking the Vineyard Sound. 5 minute drive to Oak Bluffs Center, beach, dining, movies, stroll the harbor, view the famous Ginger Bread cottages. Amenities... View all property information
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    €2,689
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    About this property
    The best of both worlds! This delightful newly furnished 'modern cottage', in Tashmoo Cove overlooks the 4th hole in Mink Meadows. Plus it is a short distance to a private association sandy beach, six association tennis courts and an in ground pool with a bath house. The first floor features a... View all property information
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    €1,739
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    About this property
    Charming and spacious summer cottage. Features a beautifully landscaped yard, and great screened in porch for summer dining and relaxing. This recently renovated and impeccably maintained home offers multiple living spaces for your enjoyment. Two 2nd level bedrooms sleep families of 5 comfortably.... View all property information
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    €3,014
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    1 / 16
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Amenities and Features include... Central Air, Additional amenities include: coffee maker, lobster pot, food processor, washer / dryer, cd player, landscaped, outside shower - enclosed, phone ld block, outdoor furniture, ironing board. View all property information
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    €9,645
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    About this property
    Architect designed luxury waterfront retreat sits overlooking 500 feet of private lagoon beach and maintains sweeping waterviews up the lagoon. The pool and patio areas take full advantage of the views. Dine and relax by the pool with pool side hot tub and the all new deck being constructed with... View all property information
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    €2,226
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    About this property
    Amenities and Features include... Waterview, Central Air, Wifi Hi Speed Internet Additional amenities include: coffee maker, patio table and chairs, lobster pot, food processor, washer / dryer, landscaped, outside shower - enclosed, outdoor furniture, ironing board. View all property information
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Wonderful water views from this second floor end condo. Located right across the street from State Beach, this condo is within walking distance to the center of Oak Bluffs. Beautifully furnished and appointed, you can enjoy your vacation and leave your car at home. Come and relax on Martha's... View all property information
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    €10,201
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    About this property
    This waterfront luxury retreat, designed by Hutker Architects, sits quietly perched above the Lagoon, with a large pool, private beach and sweeping water views. 'Sandy Point' takes its name from the unique private beach below with its prominent point of sand that juts out into the Lagoon. Private... View all property information
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    €1,855
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    About this property
    Our 'treehouse' is the tallest residence in the town of Oak Bluffs. Enjoy quiet and seclusion in this wooded setting, located in the exclusive Meadow View Farms community. There are panoramic views from the upper level, above the treetops. The bike path and MVTA (bus) are steps from the door, and... View all property information
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