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Oak Bluffs Luxury Holiday Homes

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    Travellers to Oak Bluffs are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    34 Matching Rentals in Oak BluffsView all 231 rentals
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    7 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 7 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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    • Hot Tub
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    • Private Outdoor Pool (Heated)
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    Smoking allowed
    About this property
    This upscale, newly renovated, 4 bedroom home in a quiet neighborhood in Oak Bluffs. You are 2.5 miles from the town center and Inkwell and State beautiful public beaches. This home boasts a large unground back yard pool and hot tub on the mahogany deck. Large outdoor shower. Grill and fire pit...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 22
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    About this property
    Prime waterfront location with stunning water views of the Vineyard Haven Harbor. Sit on the private deep water dock, fish and watch the boats go by. Built in 1890 and renovated in 2002 is this expansive five bedroom home with five bathrooms. The property included a boathouse with kitchenette and...
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    Oak Bluffs, Martha's Vineyard 02557
    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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    • Waterfront
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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, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    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...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    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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    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    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
    Kid friendly
    Smoking allowed
    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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    • Patio
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    • Private Outdoor Pool (Unheated)
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    • Grill
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    Pet friendly
    Kid friendly
    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)
    • Patio
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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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    • Internet Access
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    Pet friendly
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    Smoking allowed
    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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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Patio
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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. 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...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 5 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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    • Waterfront
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    Pet friendly
    Kid friendly
    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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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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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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    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, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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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, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    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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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    About this property
    This is an original Pratt house built in 1866 by the famed architect Pratt for whom the Pratt Institute in New York was named. It is located in the historic district across from a large park in which baseball, golf practice, kite flying, bike riding, picnics and even, on at least one occasion,...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    6 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Cable/satellite TV
    • Porch
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Pennacook house in Oak Bluffs on the charming island of Martha's Vineyard is beautifully maintained, bright and sunny, with a large eat-in kitchen, living room, dining room, and library with WIFI. Play outside on the large lawn, relax in the hammock, watch sunset from the front porch and enjoy...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 11
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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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
    Kid friendly
    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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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • Grill
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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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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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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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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
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    • Ocean Views
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    • Housekeeping Included
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    Pet friendly
    Kid friendly
    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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    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 10 Quick View
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    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
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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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    BURBS - Stylish New Home, Central AC, Wifi, Screened Porch1 / 19
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Reviewed 29 July 2014
    Arrived a little early, was able to get keys right away. Lisa, was extremely pleasant to work with. The house was more than I could hope for, just immaculate. The layout was...
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    About this property
    Lovely spacious 3+ bedroom, 3.5 bedroom home within a mile from Oak Bluffs Center and beach area. Fully furnished screen porch. This home has been tastefully furnished throughout and will sleep families of 9 comfortably. \n Amenities and Features include...\n \nStylish New Home, Central AC,...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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