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Oak Bluffs Luxury Holiday Homes

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    Travellers to Oak Bluffs are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    34 Matching Rentals in Oak BluffsView all 233 rentals
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    7 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Heated Pool, Hottub,AC,WiFi,sleep22, 2 mi to beach1 / 49
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 22 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    About this property
    Walk to everything from this 5 bedroom home located in the heart of Oak Bluffs. Spectacular views of Oak Bluffs Harbor and Nantucket Sound. Steps away from ferries and seconds away from restaurants, shopping, Ocean Park and State Beach. Additional amenities: Close to Town, Coffee Maker, Games,...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    This welcoming air conditioned waterfront house and guest house is privately set with panoramic water views of Lagoon Pond, Hines Point, the draw bridge, Vineyard Sound and Cape Cod. The main house has a generous open layout with substantial living room, dining, and sitting areas that allow for...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 12
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    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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Garden
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    Pet friendly
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    About this property
    Beautiful, spacious, 6 bedroom 4 full, 2 half baths set in a quiet and private area of Oak Bluffs, close to Edgartown, Vineyard Haven, area beaches and attractions. This home comfortably hosts extended families with multiple living spaces. The main living level features 2 master bedrooms (one...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    This wonderful four bedroom home is conveniently located in Oak Bluffs is just off the bike path and less than two miles to downtown Oak Bluffs. Inside the home offers an open floor plan with chefs kitchen, comfortable living room and dining room with cathedral ceilings and beautiful fireplace. Two...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Oak Bluffs retreat featuring 18 X 30 foot pool, outdoor patio with sectional sofa seating, spacious dining deck and three levels of luxury living. The outstanding home has been professionally decorated by one of the islands premier decorators. This house is privately situated in an enclave of...
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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
    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...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    WATERFRONT HOME WITH PRIVATE BEACH1 / 25
    (1)Excellent
    7 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    Located on over 1 acre of waterfront property on East Chop, an exclusive area of historic Oak Bluffs, this unique home is perfect for family and friends that want to vacation together while allowing for separation. This home can accommodate up to 12 people. No longer need to rent multiple homes on...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 12
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    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....
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
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    • Ocean Views
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    Pet friendly
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    Smoking allowed
    About this property
    This fabulous 125 year-old Victorian cottage was lovingly updated and completely restored in 2012. Sitting on a large private lot, just steps from Inkwell beach, Solera offers the perfect balance of comfort, ambiance and vintage charm. The large, airy gourmet kitchen was featured in This Old House...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    OAK BLUFFS VICTORIAN ONE BLOCK FROM BEACH, TWO BLOCKS FROM TOWN!1 / 23
    (1)Very good
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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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, basketball and a playground and four blocks from town. Enjoy the water view of Vineyard...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Newly Renovated with Fabulous ocean views1 / 19
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    • Ocean Views
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This magnificent 1920’s East Chop cottage has been extensively redesigned, refurbished and expanded to allow friends and families to enjoy luxury accommodations along with rare double views of both Nantucket Sound and neighboring Crystal Lake. Complemented with a huge wrap around deck and a covered...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a beautiful new home in Sengekontacket that has all your vacations needs taken care of. The first floor has an open floor plan with a gourmet kitchen, living room with fireplace and large dining space. There are sliders that open to the outdoor patio area. There is also a master suite...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, location, location is what it is all about at this fabulous restored ginger bread cottage. The home is a hop, skip and jump to Inkwell Beach and walking distance to Circuit Ave. and all the shops and restaurants. Enjoy relaxing on the covered porch and the fantastic views of the ocean...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    Pet friendly
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    About this property
    2 Harrison, formerly part of the Ahoma Inn, is over 175 years old. It provides all of the amenities you're looking for in a summer vacation, within walking distance of beaches, towns and public transportation. We include luxury linens, a fully stocked kitchen, oversized charcoal grill, beach...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
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    About this property
    Up one flight of stairs is this lovely three-bedroom Sail Loft with its own private entry. It features a Queen size bed in the master bedroom, twin beds in the second room, and a queen size sleeper sofa in the spacious Cathedral-ceiling living room, which comfortably sleeps up to five people. The...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Completely renovated cottage in the Sunset Lake area of Oak Bluffs. Walk to town and library. Completely renovated modern kitchen. Rock away on the large front porch. Additional amenities: CD Player, Coffee Maker, Fans, Games, Lobster Pot, Outdoor Shower, Vacuum, Wine Glasses
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    Oak Bluffs, Martha's Vineyard 02539
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This grand Victorian jewel on Ocean Park has been completely renovated and transformed into a beautiful vacation home. The first floor has a beautiful chefs kitchen that opens to dining room and family room. There is a bedroom with private bath on this floor. The second floor has three...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New Listing for 2018 Summer Season! Interior features, main living area, lower level family room, open kitchen and dining area, five bedrooms including two master bedrooms en-suite, two bedrooms on 2nd level that share a hall bath and children's/teen bunk room on the lower level and a bath located...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    • Air Conditioning
    • 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 and public beaches The use of coastal colors and upscale furnishings throughout combine to make this gorgeous Oak Bluffs summer home a cut a...
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    Oak Bluffs, Martha's Vineyard 02536
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 1 Bathroom, 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...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 5 Bedrooms, 1 Bathroom, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    This gorgeous, contemporary air-conditioned private home is perfect for your luxurious vacation on the island. It is 2700 sq ft of well laid-out space and sits on 1.4 acres of land in a private wooded area, centrally located, only minutes from downtown Oak Bluffs and beautiful beaches. The...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    About this property
    Just a block from the East Chop Bluffs on a sleepy side street in a quiet wooded setting. There are 2 SEPERATE LIVING ROOMS!! Large bright kitchen that accesses a separate dining room, inviting screen porch with dining and sitting areas, and sunny rear deck with lots of backyard privacy. Ocean...
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    Oak Bluffs, Martha's Vineyard 02257
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
    About this property
    Sprawling Oak Bluffs home with five bedrooms and 3 full bathrooms. The home is located about a half mile walk to Oak Bluffs center and about a 1 mile walk or bike to the Inkwell Beach and close to Oak Bluffs Library. The first floor features open kitchen and dining/living room area along with four...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Secret of Life1 / 14
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
    • Balcony
    • Porch
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    Pet friendly
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    Reviewed 4 July 2017
    Secret of Life is a really excellent holiday home. It is spacious, modern andcomfortable and within easy walking distance of the lovely Oak Bluffs. The owners had taken the...
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    About this property
    JUNE & JULY RATES REDUCED!! You will be within walking distance from downtown shopping, movie theatre, restaurants, bike path, harbor, beaches, and two-tenths of a mile from the brand-new modern library. Relaxed and warm, this brand-new home is expertly decorated. The open floor plan and two...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Stylish, contemporary, light filled cape home has been completely renovated to include a now open concept main level, hosting the main living room with 50 ' smart TV and huge bay window, chef's kitchen, dining area seating 8, a 2nd casual media area with 2nd 60' smart TV, master bedroom en...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Outstanding, Contemporary Farm House Design, has just been renovated and professionally decorated top to bottom, by one of the islands premier firms, featuring 4 levels of luxury living. The main Living Level offers open design Living Area, Dining Area and Chef's Kitchen with expansive center...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 10
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