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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.
    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, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beautiful new contemporary house with four bedrooms and four bathrooms, finely appointed and tastefully decorated. Association Tennis, Central A/C, Wifi. This home is located in a highly desirable area close to town and beaches. The house overlooks a meadow and provides the perfect setting for a... View all property information
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    Oak Bluffs, Martha's Vineyard
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    6 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    Amenities and Features include... In-Town, Walk to Beach, Wifi Internet Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, cd player, landscaped, outside shower - enclosed, outdoor furniture, ironing board. View all property information
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    Oak Bluffs, Martha's Vineyard
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Outdoor Dining Area
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    About this property
    A comfortable ranch with all the amenities for a perfect vacation. It's quiet location is 1.5 miles from town, yet not too far to bike or walk in when needed. Beaches, ponds, the lagoon, and other recreational facilities are also easily accessible if you want to hop on the bike path around the... 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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    • Patio
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    About this property
    This cozy, quaint waterfront property offers beautiful sunsets and great harbor views. Swimming, boating, kayaking, are just steps from this warm and charming quintessential Vineyard cottage. Amenities and Features include... Waterfront, Waterview Additional amenities include: dock/boat-slip,... 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
    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
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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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    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Satellite TV
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    About this property
    Classic vineyard cottage renovated, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. Main living level features a lovely kithcen very well stocked with dining and cook items, a large sunporch living area and 2nd aliving area with large screen TV. Three lovely... 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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    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
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Newly renovated home across the street from the lagoon and sailing camp! This home features, new stainless steel appliances, granite counter tops with an island. Five minutes away from town and beaches this property is perfectly located. The main floor has central air, an open floor plan with... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    .Leave your worries and your car behind — this picture perfect Vineyard beach house is steps from downtown Oak Bluffs, the sandy beach and a few short blocks from the ferry. Recently renovated and restored, four-bedrooms and one and a half baths, offering the perfect juxtaposition of cottage charm... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Terrace
    • Balcony
    • Satellite TV
    • Wi-Fi
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    • Air Conditioning
    • Private Garden
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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, parking. Overlooking a park, sip your coffee on the upstairs... 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
    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
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    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Classic, 'Camp Ground' over sized 7 bedroom 3 bath home in a residential neighborhood within easy walking distance to the beach, shops, restaurants, galleries, etc. It offers double master bedrooms (1st and 2nd floor.) Enjoy rocking on our huge front porch in over sized Georgia rockers. As you... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
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    • Pet-friendly
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    About this property
    Adorable waterfront cottage, pristinely maintained throughout the years. Enjoy privacy and views from the spacious deck. 3 minute walk to great sandy lagoon beach - a perfect place for young children to play. Centrally located just 2 miles to either Vineyard Haven or Oak Bluffs town centers.... View all property information
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    Oak Bluffs, Martha's Vineyard
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Central Heating
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    • Elder access
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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
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Central Heating
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    • Satellite TV
    • DVD Player
    • Porch
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    • Pet-friendly
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    About this property
    This 3.5 bedroom home with skylights, 52 inch Tv, computer, internet, printer, fax, is your home away from home. 1 mile from town 1.5 mile from beach and 7 miles from airport is ideal location. 2 SETS OF GOLF CLUBS AND 4 TENNIS RACQUETS FOR YOUR USE, 3 CABLE TV'S, MASTER BATH HAS WHIRLPOOL TUB... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Balcony
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    • Satellite TV
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    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Newly refurbished, stately 4262 sq ft. home with 4 bedrooms, 2.5 baths situated within a five minute walk to the center of Oak Bluffs, beaches, and ride/jog to bike trail. Large fenced yard with shared tennis court and patio. Spacious, open 35x45 living room downstairs with smaller living room,... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    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
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    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    The quintessential Vineyard cottage!!! This sweet cottage brings back visions of the lazy days of summer of bygone eras when life was less hurried. The serene location overlooks a pond, a barrier beach with a few homes, and the Outer Harbor. It has a magnificent 180 degree view of Vineyard... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Hot Tub
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    About this property
    Walk to town from this meticulously maintained, large & airy, 3 bedroom, 3 full bathroom vacation getaway, located on a beautiful 1/4 acre lot on a quiet street. Watch your troubles sail away while relaxing on the large farmer's porch with your favorite summer beverage, or grilling with family and... 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
    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. Amenities and Features include...... 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
    Amenities and Features include... Walk to Town and Beach, Newly Renovated Additional amenities include: coffee maker, patio table and chairs, lobster pot, washer / dryer, landscaped, outdoor furniture, ironing board. View all property information
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    Oak Bluffs, Martha's Vineyard
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Waterfront
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    About this property
    Historic harborfront home with private dock has been completely renovated and newly furnished, beautifully appointed throughout to reflect summer living on the Vineyard. The large living and dining areas open onto the expansive and comfortably furnished porch, overlooking picturesque Oak Bluffs... View all property information
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    Oak Bluffs, Martha's Vineyard
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    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    About this property
    Wonderful four bedroom, two bath home completely redecorated. Features wrap around porch, living room and sun porch/TV room. Amenities and Features include... Classic Oak Bluffs Summer Home, Walk to Town and Beach, On Street Parking Additional amenities include: coffee maker, patio table and... View all property information
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    Oak Bluffs, Martha's Vineyard
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    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Patio
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    • Pet-friendly
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    About this property
    Gracious 5 bedroom in-town victorian offers easy access to shopping, ferry, park with basketball and tennis and beach. This home has been lovingly maintained and restored to it's prior elegance. Enjoy cocktails on the beautiful three season porch. Additional amenities include: nearby bank, close... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Patio
    • Shared Outdoor Pool...
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    About this property
    Immaculate, waterview town house located in the desirable Sengekontacket Pond area of Oak Bluffs. Wonderful waterviews of Sengkontacket Pond and Nantucket Sound. This spacious unit offers a bright open airy feeling with three levels of living area. The main floor includes bedroom, living, dining... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • Child-friendly
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    • Elder access
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    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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Please note - all new master bedroom and bath completed in 2014 (not shown in photos) Amenities and Features include... Sengekontacket, Central Air Additional amenities include: coffee maker, patio table and chairs, lobster pot, food processor, washer / dryer, cd player, landscaped, outside... 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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    • Child-friendly
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    About this property
    In Town, walk to beach, tennis and town area. This wonderful family home has a large wrap around porch, 7 bedrooms and sleeps 12-14. Many areas of this wonderful older home have been updated. Hi Speed Internet. Amenities and Features include... 1 Block to Beach, Wifi Internet, Linens Provided,... View all property information
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    Oak Bluffs, Martha's Vineyard
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    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 with comfortable living areas, modern kitchen, AC in all bedrooms. The first level features an open floor plan, the dining... 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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    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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    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    This grand ginger bread cottage recently updated, offers lots of living space on 2 levels, with a kitchen, living room and full bath on each level. Perfect for extended families looking to spend vacation time together while enjoying expansive living space on two levels. The access stairs to the 2nd... View all property information
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    Oak Bluffs, Martha's Vineyard
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wheelchair access
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    About this property
    Beautiful and spacious 3 bedroom in Oak Bluffs, Martha's Vineyard. Sunny, open and airy Cape. Walking distance to town, gingerbread cottages, library, and playground. Close to beach, golf course, and great fishing spots. There is a pack and play in the upstairs bedroom for a baby to sleep or nap... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
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    MVVR EXCLUSIVE: Adorable pristine beach cottage has spectacular views across the sound, calm water swimming, great area for kayaking. The opening kitchen, dining and living areas are enhanced by the wall of windows faciing 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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    About this property
    MVVR EXCLUSIVE: Custom crafted tri-level, this beautiful home features spacious open living spaces, hardwood floors throughout, 3 full baths, central A/C and WiFi. Exterior features include a large private deck at the back of the house, the perfect venue for summer dining or just relaxing with a... View all property information
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    Oak Bluffs, Martha's Vineyard
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    5 of 5 stars (6) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Satellite TV
    • Washer
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Patio
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    This welcoming home is freshly renovated and decorated in calm and comfortable Vineyard style, with hand-hewn, antique and designer furnishings. The house is ideally located on a quiet street, within easy walking distance to the village, harbor, beaches, waterfront parks and historic Victorian... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    5 of 5 stars (2) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
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    • Grill
    • Porch
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    • Pet-friendly
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    • Child-friendly
    • x
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    About this property
    Sun filled and airy prow front contemporary home with beautiful views of Lagoon Pond. Four bedrooms accommodating up to eight guests. Two full baths plus refreshing outdoor shower. The second floor with its cathedral ceiling utilizes an open living room, dining room and kitchen floor plan to... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
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    • Child-friendly
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    About this property
    Privately situated on a hilltop in Sengkontacket, -spacious tri-level 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
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This grand ginger bread cottage recently updated, offers lots of living space on 2 levels, with a kitchen, living room and full bath on each level. Perfect for extended families looking to spend vacation time together while enjoying expansive living space on two levels. The access stairs to the 2nd... 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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    • Child-friendly
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    • Elder access
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    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
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Porch
    • Satellite TV
    • Internet Access
    • DVD Player
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
    • ?
    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 / 23
    5 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Grill
    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Outstanding, custom crafted 5 bedroom 4.5 bath luxury nestled within Farm Neck golf course and over looking Sengkontacket Pond, lovely waterviews from the house. Large family living spaces include a great room with soaring ceilings opening to the patio, spacious family room, New for 2016 lower... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 25
    7 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
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    • Porch
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    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Waterfront Compound on Lagoon with panoramic water views. The main house features an open and spacious living area with comfortable furnishings, a dining area and a spacious kitchen with new appliances. The master bedroom with king bed has a private bath and opens onto a private deck. The second... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 31
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • DVD Player
    • Waterfront
    • Satellite TV
    • Private Outdoor...
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Architect designed luxury waterfront retreat sits overlooking 500 feet of private lagoon beach and maintains sweeping waterviews up the lagoon. The pool and patio areas take full advantage of the views. Dine and relax by the pool with pool side hot tub and the all new deck being constructed with... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 27
    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Grill
    • Satellite TV
    • DVD Player
    • Porch
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Seaside Cottage Style Vacation Home. Recently renovated. Perfect for extended families. Walk to Oak Bluffs town center, beach across the street and miles of beach side - bike paths begin just a couple of hundred yards from the house. Ocean views from just about all rooms. Wonderful, large summer... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard