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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.
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    1 / 20
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our picture-perfect home is an excellent summer escape. Spacious double lot makes this setting seem like a parkland. It's just a 15-minute walk to downtown Oak Bluffs and the town beach. It's also on the public transit line and the bike path. View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 15
    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... View all property information
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    Oak Bluffs, Martha's Vineyard
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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 / 21
    5 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    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, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    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 association beach. This is also a great spot for children to... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    8 Bedrooms, 8 Bathrooms, Sleeps 20 | Quick View
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    • Hot Tub
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    About this property
    Amazing five acre property! 6 BR main house w/ pool + a 2 BR carriage house! Our amazing property is perfect for everything from a memorable family vacation to a serene retreat. You and your guests will begin to enjoy the feeling of privacy the minute you arrive as you drive down the long tree... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    A new Cape style residence 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 lead out onto a nice... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    1 / 22
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Outstanding, custom crafted estate home with 6 bedrooms and 5.5 bath all nestled on 2 acres of meadow and landscaped grounds overlooking Farm Neck golf course with waterviews of Sengekontacket Pond. Enjoy the expansive and peaceful views across the landscaped grounds , meadows and waterviews in the... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 27
    4 of 5 bubbles (1) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 13 | Quick View
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    About this property
    Newly renovated 5 bedroom home just a mile and a half from the center of Oak Bluffs. New hard wood floors throughout as well as updated furnishings and decor. Dining area is extended by a nice sized sunny deck for outdoor dining. Perfect for a large family vacation. Additional amenities include:... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 28
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 17
    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
    1 / 23
    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
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Come and enjoy the newly renovated two bedroom home in Oak Bluffs. The first floor which is done in bright coastal colors has a nice eat in kitchen with a couple steps up to the living room with a large flat screen TV. The first floor also have a half bath. The second floor has two bedrooms and... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 37
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Waterfront
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    • x
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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 private... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 11
    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Beautifully upgraded 5 1/2 Bedrooms 2 1/2 Bath, Formal Dining room, and a Veranda! Spacious outside deck for family, friends and Fun! Less than a block away from the beautiful beach and a leisurely walk to town. Weekly rental on Season ( July thru August) Saturday to Saturday. (May and September a... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Porch
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    • x
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    About this property
    Enjoy the charm of a Vineyard cottage with all the amenities of today. This 3 bedroom house has brand new furnishings for 2015. It is in a quiet neighborhood not far from Oak Bluffs center and its harbor. The house is also close to the bike path. The house has an open floor plan with a large... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Pet-friendly
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    • x
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    • x
    About this property
    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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    1 / 21
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
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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
    1 / 21
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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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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    Oak Bluffs, Martha's Vineyard 02557
    1 / 18
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
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    • Pet-friendly
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    • x
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    • x
    About this property
    Nestled in a private location on Crystal Lake which abounds with bird life, this is a delightful, vintage 1950's home with modern conveniences and comfortable furnishings. Its rambling single story layout is spacious and conducive to relaxed living. It is very well maintained and well equipped. The... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 16
    3 of 5 bubbles (2) Average
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Terrace
    • Balcony
    • Satellite TV
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    • Private Garden
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    • Pet-friendly
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    • x
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    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... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 43
    6 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    The Weku House is a luxury, 5,000 square foot home located in the beautiful town of Oak Bluffs on Martha’s Vineyard. Originally built in the year 2000, this home was fully renovated in 2015. Elegantly decorated with designer furnishings and interior appointments, the meticulous attention-to-detail... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 15
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    About this property
    This classic Gingerbread House is less than a block away from the beach in Oak Bluffs. Surrounded by parks in a residential neighborhood, the property is easy walking distance to shops, restaurants, harbor, galleries, etc.. This house is spacious with high ceilings and over-sized rooms. The... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beautiful four bedroom house in the prestigious Farm Neck area overlooking a lovely lawn to a large tidal pond. This home offers an open floor plan so the whole family can be together. The kitchen and living areas open up to a wonderful deck so you can enjoy the views of Sengekontaket Pond.... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 21
    4 of 5 bubbles (1) Very good
    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    This well maintained, vintage Victorian home is centrally located, yet away from the hustle and bustle of town: just one block from the beach, two blocks from Waban Park and Ocean Park, three blocks from tennis, backetball and a playground and four blocks from town. Enjoy the waterview of Vineyard... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 5 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick 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... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 31
    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
    1 / 22
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    New for the 2016 season! Enjoy this wonderful new three bedroom three and half bath home in Oak Bluffs. The first floor has an open concept with a beautiful chefs kitchen, large dining room and family room with TV. The first floor also has a master bedroom en suite with a king size bed and TV.... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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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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    Oak Bluffs, Martha's Vineyard
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    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Come and enjoy this beautiful waterfront home on East Chop! The first floor has a wonderful front seasonal porch with views of the Vineyard Sound. There is a large dining table and room to relax and take in the view. There is also a living room that leads into the kitchen on the 1st floor. The... 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
    A recent renovation has moved this home to the top of the list in terms of comfort in a tastefully decorated waterfront home. A new family media room has been added giving extended families lots of space to relax. The open concept kitchen, dining and living areas feature waterviews and open onto a... View all property information
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    Oak Bluffs, Martha's Vineyard
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    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Come and let your cares float away as you relax on the enormous first-floor front porch or second-floor open deck of this charming 100+-year-old home looking out onto the beautiful Nantucket Sound. The home is sunny, bright and spacious and has a relaxed elegance with a large open living room... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Sea breezes and fabulous water views from almost every room are the mainstay for this unique waterfront home on the Lagoon Pond in Oak Bluffs. Polished with soothing designer furnishings in layers of cappuccino and white neutral linen and cotton, you will enjoy this European-chic interior almost as... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 37
    6 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beautiful immaculate home, privately located in the Farm Neck area. Extended families will enjoy this open airy home with expansive deck, roomy and comfortably furnished screened porch, great location with easy access to Bike Paths, Oak Bluffs, Edgartown and beaches. Association dock a minute’s... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 29
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    About this property
    It's all about the stellar location of this five-bedroom Oak Bluffs getaway, a wonderfully renovated Victorian home with a front porch and deck, four bikes to help you explore Martha's Vineyard, and an enclosed yard that is ideal for kids. This two-level house sits just half a mile from the... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Grill
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • 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
    1 / 17
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Porch
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    For those who love an in-town location this area known as the Campground with the historic Tabernacle is the ideal location. The sweet and colorful cottage is pristinely maintained by the owner. Rockers line the porch for your outside enjoyment. The main level hosts the living room with TV ( not... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 33
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Waterfront
    • Grill
    • Internet Access
    • Air Conditioning
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 15
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    1 / 28
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Satellite TV
    • DVD Player
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This wonderful family vacation home features lovely waterviews across Crystal lake. The peaceful location and large yard provide the perfect venue for extended families with children. Relax on the expansive deck, enjoy the views from the 4 person glider swing as seen in the photos Families will... 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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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Grill
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Quietly nestled on quiet street just on the outskirts of town, this brightly lit home features a mix of coastal details and traditionally styled upscale furnishings for your comfort. The interior has open floor plan that flow nicely to outdoor living spaces including a screened porch and brick... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 26
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Come and enjoy this three level contemporary home with a beautiful landscaped yard. There is a wonderful deck off the kitchen with outdoor dining and seating area. the first floor offers and open kitchen, dining and TV/living room area. The is a second sitting room on this floor as well. The... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    1 / 16
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This house, built in 1865 it is a unique Victorian home, wonderful for family gatherings. The location is ideal - it sits at the heart of Ocean Park, with the closest access to Circuit Avenue of any of the homes on the Park. The home was recently renovated, including central air with two zones.... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    1 / 13
    5 Bedrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Private Garden
    • Secure Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Newly renovated, and located right off of the main strip, Circuit Ave. Updated appliances, free WIFI, and great air conditioning.. Outdoor amenities include a double-grill, a Gazebo, and a full deck. The deck is also equipped with solar lights that come on in the night time. The house is also a... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 01060
    1 / 17
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Private Garden
    • Parking
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This house is situated right on the main strip in Oak Bluffs. It is on Circuit Avenue a minute walk away from restaurants and stores like Vineyard Vines. It is a 2 story house with 1 bedroom on the first floor and 4 on the second floor. 1 bathroom on each floor. This house is currently being... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02568
    1 / 18
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    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... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557