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Vacation Rentals in Oak Bluffs, MA

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    All 277 Rentals in Oak Bluffs
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    Travellers to Oak Bluffs are booking June dates now. Secure your vacation rental today, and have the perfect trip.
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    From
    $3,705
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    1 / 15
    5 Bedrooms / 2 Bathrooms / Sleeps 8
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    $2,612
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    5 Bedrooms / 5 Bathrooms / Sleeps 10
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    1 / 16
    4 Bedrooms / 1 Bathroom / Sleeps 8
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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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    1 / 22
    5 Bedrooms / 2 Bathrooms / Sleeps 10
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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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    1 / 11
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Stylish Cape located close to town and beach.attention to detail in every room. Relax and enjoy all the comforts of home in this all new pristine 3 bedroom, 2 bath home. The main living level features an open kitchen living and dining with AC. In additon there is separate TV room with office area... View all property information
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    1 / 20
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    Owner Transfer Ferry Tickets Included in Rate for Available July Weeks - Please Inquire 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... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Cute cottage located walking distance to Circuit Avenue and the beach. No need to bring you car, restaurants, bars, grocery store all are walking distance from this home.Four bedroom, two bath home with all the amenities you will need on your vacation. Across the street is a park for the kids,... View all property information
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    $1,640
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    1 / 16
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    About this property
    With Inkwell Beach at your door step, sweeping ocean views from your private deck and Living Room, and walk-to-town convenience, this Waterside Condo offers a unique vacation getaway in Oak Bluffs. Located directly across the street from popular Inkwell Beach, the second floor condo enjoys sweeping... View all property information
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    1 / 13
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    This three bedroom two bath Cape has been recently renovated and tastefully decorated. Spacious deck for BBQ or relaxing while the children play in the yard. This home has a water view of the Lagoon from the side of the home. Come and enjoy your stay on Martha's Vineyard! Additional amenities... View all property information
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    1 / 22
    3 Bedrooms / 2 Bathrooms / Sleeps 9
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    About this property
    Surrounded by a green part shade, part sunny yard with a patio deck for basking in the sun or grilling outdoor dinners, this house is located on New York Ave half a mile from the beach. A lovely sleeping porch adds room for more in this colorful and welcoming home. An informal dining room and a... View all property information
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    $6,681
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    1 / 20
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    About this property
    Set in a quiet section of Meadow View Farms, this contemporary farmhouse is nicely styled throughout and conveniently located between Oak Bluffs and Vineyard Haven. The first floor features a large Living Room with vaulted ceiling, fireplace, media center, and sliding doors to the back deck and... View all property information
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    1 / 16
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
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    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    About this property
    NEW FOR THE 2015 SEASON! BETTER PICTURES FORTHCOMING - HOUSE WILL HAVE ALL NEW FURNISHINGS AND FRESHLY PAINTED TO GIVE IT THAT VINEYARD BEACHY FEEL! PLEASE INQUIRE FOR MORE INFORMATION. Views, Views and more Views! Lovely water views of Sengekontacket Pond over the rolling 'forever' conservation... View all property information
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    $2,095
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    1 / 13
    3 Bedrooms / 1 Bathroom / Sleeps 5
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    About this property
    Bright and newly remodeled classic summer cottage. Conveniently located just one mile from Oak Bluffs town center, Ink Well Beach, shops, fine and family dining, historic Flying Horses Carousel, public tennis courts, Bandstand Park and Oak Bluffs Harbor-front area. The professionally landscaped... View all property information
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    $3,158
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    1 / 13
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    About this property
    Beachfront living combined with the convenenience of in-town. This condo makes your Vineyard vacation easy. Enjoy sweeping ocean views of Nantucket Sound and Chappaquiddick, with Oak Bluffs' popular Inkwell Beach directly across the street. Enjoy a second floor condo with water views from the... View all property information
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    $2,369
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    1 / 11
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Grill
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    • Water Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    East Chop - 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 the... View all property information
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    1 / 14
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Suitable for children
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    About this property
    Perfect location for golfers near hole #8 on Farm Neck Golf Course! This home offers four bedrooms and two and a half bathrooms.  Spectacular water views over Sengenkontacket and ocean and much more! Close drive or bike ride to State Beach. Enjoy your stay on the Vineyard with comfort and style. View all property information
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    $5,831
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    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
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    • Satellite TV
    • Waterfront
    • Water Views
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    • Smoking allowed
    • Suitable for children
    • x
    • 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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    1 / 26
    5 Bedrooms / 3 Bathrooms / Sleeps 9
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    About this property
    Relax and enjoy your summer vacation at this great home on Farm Pond in Oak Bluffs. Owned by the same family since 1932, this property defines authentic Vineyard charm! The house is on one level, with the master on one side and three bedrooms at the other end of the house. In between is a large... View all property information
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    1 / 41
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Pets allowed
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    • Suitable for children
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    About this property
    Gorgeous East Chop.Luxury+ location= Vineyard Ideal.This beautiful East Chop home is for the guest who expects only the best the Vineyard has to offer. Head out in any direction and quickly find beach, tennis, lighthouse, water, town, all walking distance.The gourmet kitchen has every amenity and... View all property information
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    1 / 16
    5 Bedrooms / 3 Bathrooms / Sleeps 11
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    About this property
    Light filled, spacious and above it all. This quiet residence is situated in Oak Bluffs' exclusive Meadow View Farm community. Close to bike paths (bikes come with the rental) and the MVTA bus and close to Sengekontacket for Pond bathing and kayaking. Additional amenities include: beach chairs,... View all property information
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    2 Bedrooms / 1 Bathroom / Sleeps 5
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    • Wi-Fi
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    About this property
    The Blue Canoe is completely fresh and renovated, while its 1910 charm is fully intact. It has a lovely deck and a huge side yard surrounded by a split rail fence just perfect for enjoying summer lounging and games. The house is in a neighborhood central to many things including being just steps to... View all property information
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    1 / 16
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    Outrageous views from this third floor condo #304) overlooking the beach in Oak Bluffs. Walk to Circuit Avenue for all the happenings in town. Well equipped and nicely decorated, this is a great get-away venue. Elevator, parking, convenience. Additional amenities include: beach chairs, sofabed,... View all property information
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    1 / 10
    1 Bedroom / 1 Bathroom / Sleeps 4
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    About this property
    Cozy guest house sleeps 4. Open floor plan with queen bed alcove off of living room. One bedroom with one set of bunk beds. Large deck with view of Lagoon. Owner or guests occupy main house. Amenities and Features include... Lagoon Guest House, Walk to Private Lagoon Beach Additional amenities... View all property information
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    1 / 16
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    Adorable Beach Chic Cottage and oh so nicely decorated. Walk to Town Center, Harborfront, Parks and Inkwell Beach. Amenities and Features include... Walk to Town and Beach, Wifi Internet Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer /... View all property information
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    3 Bedrooms / 1 Bathroom / Sleeps 5
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    About this property
    Lovely contemporary home in one of the Islands premier community settings, Waterview Farms. Close to Farm Neck Golf Course and tennis and a short distance to town and beaches. Amenities and Features include... Waterview Farms, Waterview Additional amenities include: dock/boat-slip, coffee... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    Tucked away on the shores of The Lagoon, this deluxe waterfront retreat has been designed with an open layout to maximize grand water views and sunsets from its decks, screened porch and most rooms. The main level of Crow's Nest features a stylish wrap-around mahogany deck, and Great Room with open... View all property information
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    5 Bedrooms / 5 Bathrooms / Sleeps 8
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    • Fireplace
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    About this property
    Beautiful luxury home overlooking Farm Neck Golf Course and Sengekontacket Pond. Large family living spaces include a great room with soaring ceilings opening to the patio as well as a large TV/family room. Expansive gourmet kitchen with dining area is great for family gatherings after the beach.... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 9
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    About this property
    Tucked behind a beautiful hedgerow, this restored bungalow is just up the hill from Oak Bluffs center and on the outskirts of East Chop. Comfortable and loaded with personality, the large living room opens to a breezy sleeping porch. A simple yet well-stocked kitchen is graced by a lovely dining... View all property information
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    3 Bedrooms / 1 Bathroom / Sleeps 7
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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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    3 Bedrooms / 3 Bathrooms / Sleeps 7
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    • Pets allowed
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    • x
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    About this property
    Newly renovated and painted campground victorian home with gingerbread accents. This charming victorian is ideally located close to town, shops, restaurants and beaches. Enjoy peeks of the harbor while watching the sunset from the new roof top deck. Additional amenities include: coffee maker,... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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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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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Hot Tub
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    About this property
    This beautifully renovated farmhouse is located in the desirable Waterview Farm neighborhood next to the third fairway of Farm Neck Golf Course and has lovely second floor views of Sengekontacket and the barrier beach. Bright, open floor plan with first and second floor master suites and a wall of... View all property information
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    1 / 32
    5 Bedrooms / 2 Bathrooms / Sleeps 10
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    About this property
    Exceptional location for this immaculately kept Victorian on Waban Park next to the Seaview Condos. Walk across the street to the beach. Walk to town. Walk right out the door to the park with ample space for children to play. The house is tastefully and colorfully decorated. The newly upgraded... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    East Chop ranch house with expansive lawn and wrap around farmer's porch.Enjoy the soft summer breeze from the porch of this charming 4 bedroom summer home. Simple pleasures and lazy afternoons await you from this East Chop cottage. Additional amenities include: bakeware, coffee maker, lobster... View all property information
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    6 Bedrooms / 6 Bathrooms / Sleeps 18
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    • Air Conditioning
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Newer home built in 2008 with 6 bedrooms, 6.5 baths located in Hart Haven in Oak Bluffs, off of Beach Road. Two private association beaches, one with raft perfect for children. Private harbor and association tennis court.Home overlooks Farm Neck golf course and has large deck, central air... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Amenities and Features include... Boutique Sweet with Designer Interior, Large Screened Porch, AC all Bedrooms, 15 Minute Walk to Oak Bluffs Center and Inkwell Beach Additional amenities include: coffee maker, patio table and chairs, washer / dryer, landscaped, porch - screened, outside shower -... View all property information
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    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • 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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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Dishwasher
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    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Absolutely delightful Oak Bluffs Victorian with colorful and charming decorating touches. Spacious and homey, this house has been cared for and cherished. Old world charm with all of today's necessities combined transport you to another era and give you all the comfort of modern times. Sleeps 8... View all property information
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    5 Bedrooms / 1 Bathroom / Sleeps 8
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    • x
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    About this property
    Penacook 5 Bedroom Cottage - short stroll down one of the nicest streets in Oak Bluffs to the beach and town. Completely, refurbished and all new appliances, furnishings, and bedding. Great backyard patio and grill area. Amenities and Features include... In Town, Walk to Beach Additional... View all property information
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    2 Bedrooms / 1 Bathroom / Sleeps 5
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    • Dryer
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    • x
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    About this property
    This cozy 2 bedroom has lots of natural sunlight with cheerful updated decor. Perfect for a family of 4 with extra room on sleeping porch for nanny or additional family member. Just a short walk to town, beach and parks. Additional amenities include: coffee maker, bakeware, lobster pot, dishes,... View all property information
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    5 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
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    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    About this property
    Custom Crafted Luxury Home on Farm Neck Golf Course This gorgeous 5 bedroom home overlooks the golf course and Sengekontacket Pond. Large family living spaces include a great room with soaring ceilings opening to the patio as well as a large TV/family room. The expansive kitchen is custom designed... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Suitable for children
    • ?
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    About this property
    OAK BLUFFS BAYES HILL: A/C, linens, towels and beach towels, WIFI Close to everything but just enough out of the way to be a peaceful family vacation destination on Martha's Vineyard. Large grassy yard, wide open porch, and private deck. Additional amenities include: longitude: -70.5982, living... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Pets allowed
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    • ?
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    About this property
    Quietly tucked away in prestigious Farm Neck Golf Club, this contemporary has sweeping waterviews of Sengekontacket Pond, State Beach and the Atlantic, as well as the 8th hole on the golf course. Situated on almost two landscaped acres, there are large wrap-around decks that afford multiple... View all property information
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    5 Bedrooms / 3 Bathrooms / Sleeps 9
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    • Air Conditioning
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    • Water Views
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    East Chop three level modern home with waterviews from each level, the second level deck makes outdoor activities such as eating an enjoyable experience. Amenities and Features include... EAST CHOP, WATERVIEW, WALK TO TOWN, CENTRAL AIR CONDITIONING, WI-FI Additional amenities include: coffee... View all property information
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    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Dishwasher
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    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • 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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    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    This distinctive home boasts one of the Vineyard's finest views of both Nantucket Sound and Oak Bluffs Harbor. Enjoy these views from the fully furnished porch or from the private terrace off the master bedroom. The house is set in landscaped lawns and gardens in an extremely quiet, scenic... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    • Suitable for children
    • x
    • x
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    About this property
    Open, airy contemporary Cape. All newly furnished, three bedrooms, 2 bathrooms. Ceiling fans in all bedrooms. A short 15 minute walk to Oak Bluffs Center and Beach, shopping, and dining. Sidewalks connect to miles of bike paths. Amenities and Features include... Walk to Town. Hi Speed Internet.... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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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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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
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    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    Walk to town and beach from this spacious modern home on a beautiful, treed lot. A delightful blend of amenities and charm. Central air conditioning. Amenities and Features include... Walk to Town, Central Air, WiFi Additional amenities include: beach chairs, coffee maker, patio table and... View all property information
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