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Vacation Rentals in Oak Bluffs, MA

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    1 / 13
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 18
    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 / 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
    1 / 22
    6 Bedrooms, 3 Bathrooms, Sleeps 13 | Quick View
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    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,... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 12
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    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 and... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    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... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    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 and... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 24
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    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... View all property information
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    Oak Bluffs, Martha's Vineyard
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    1 / 19
    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. Amenities and Features include... Farm Pond... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 36
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
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    About this property
    Note: New for Summer 2017, In ground heated 18 x 30 pool, patio dining table and 6 chaise lounge chairs. Depth of pool 3.5 to 6 feet. Oak Bluffs retreat featuring a pool, outdoor patio, spacious dining deck and three levels of luxury living. The outstanding home has been professionally decorated by... 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 / 27
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    MVVR EXCLUSIVE: Custom crafted tri-level, this beautiful sun filled home features, spacious open living spaces, hardwood floors throughout, sleeps 8 with 2 King Masters en-suite, guest king bedroom and semi-private Alcove sleeping area on the 2nd level ( see photo 23) Exterior features include two... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 22
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • x
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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 / 34
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • x
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    • x
    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.Connecting bike paths begin at the entrance to Meadow View. This sun... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 19
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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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. Amenities and Features include... Stylish New Home, Central AC, Wifi,... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 20
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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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    Oak Bluffs, Martha's Vineyard
    1 / 13
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
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    • x
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    • x
    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 room... 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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    • x
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    About this property
    Amenities and Features include... Hidden Cove, Centrally Located to Beaches and Towns, Association Tennis Courts, A/C, WiFi Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, landscaped, outside shower - enclosed, vacuum, outdoor... View all property information
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    Oak Bluffs, Martha's Vineyard
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    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Amenities and Features include... Hidden Cove, Association Tennis Courts, Association Kayak Landing Additional amenities include: coffee maker, fans - portable, lobster pot, food processor, washer / dryer, porch - screened, vacuum, outdoor furniture, tennis - association/shared, ironing board. View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    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
    1 / 15
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • 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
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 33
    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    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... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 15
    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
    1 / 31
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • x
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    • x
    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 / 20
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    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
    1 / 15
    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 in.... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 20
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    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... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 35
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • x
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    About this property
    Privately situated on a hilltop in Sengkontacket, -spacious tri-leve 4000 sq ft contemporary home. This wonderful vacation home has been updated for summer 2015, AC added, freshly painted, new carpeting and hardwood flooring and new furnishings. Set in a wonderful family friendly community offering... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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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
    1 / 28
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    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
    1 / 28
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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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 is... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 18
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    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 waterfront... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 33
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • 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
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    Oak Bluffs, Martha's Vineyard
    1 / 42
    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
    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 / 19
    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 great... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 21
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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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 / 38
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • x
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    • x
    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 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
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    Oak Bluffs, Martha's Vineyard
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    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Waterfront
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Patio
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    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Lovely cape home, all newly refurnished for 2013. First level features an open floor plan in the Dining, Kitchen and Living area. The tastefully decorated living area features comfortable furnishings and a 36" screen tv. One bedroom with a double bed and a full bath complete the living level. 2nd... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
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    6 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Amenities and Features include... Farm Neck Waterfront Home, Spectacular Views across Sengekontacket Lagoon, Short Walk to Association Lagoon Beach area for Kayaking. One mile to State Beach, Bike paths at entance to Rd run the Full lenght of Beach Rd. Additional amenities include: beach chairs,... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 23
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Porch
    • Grill
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    • DVD Player
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    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 28
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Satellite TV
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • DVD Player
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    • Satellite TV
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    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
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    Oak Bluffs, Martha's Vineyard
    1 / 29
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    1 / 24
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... 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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    • Grill
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Relax in optimal comfort at this Oak Bluffs home. It's got four bedrooms and lots of space for an ideal family vacation! You're in the heart of Oak Bluffs, within walking distance of the harbor and lovely waterfront. You can hop off the ferry to Martha's Vineyard and be here in no time. This... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557