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Oak Bluffs Summer Rentals

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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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    4 Bedrooms, Sleeps 10Quick View
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    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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 4Quick View
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    MVVR EXCLUSIVE: Adorable, pristine beach cottage has spectacular views across the sound, calm water swimming, great area for kayaking. The open kitchen, dining and living areas are enhanced by the wall of windows facing the waterfront and providing gorgeous water views . Enjoy the parade of...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, Sleeps 8Quick View
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    Spacious, immaculate 4 bedroom, 3 bath home. Large deck for outdoor enjoyment. Situated just outside the busy center of Oak Bluffs. It is a 10 minute walk to all activities, dining, movies and beach, historic Campground Ginger Bread cottages. There are walkways all the way into town. Amenities...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 8Quick View
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    About this property
    Set in a quiet community of homes just on the outskirts of OB, this outstanding home provides a peaceful get away yet is just a short drive to town center. The use of coastal colors and upscale furnishings throughout combine to make this gorgeous Oak Bluffs summer home a cut a above. Expansive...
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    Oak Bluffs, Martha's Vineyard 02536
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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    6 Bedrooms, Sleeps 13Quick View
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    This outstanding Oak Bluffs home is undergoing a complete face lift for the 2012 rental season and is sure to please. Spacious and perfect for extended families, featuring multiple attractively furnished living areas and sleeping 13 comfortably. The lower level of the house features a queen bed,...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 13
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    5 Bedrooms, Sleeps 10Quick View
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    About this property
    Classic & charming, turn of the century "campground" home situated on a 4,400 sq. ft. corner lot just a few minutes walk from the beach & town. Spacious & light rooms w/ some intimate spaces, a formal dining room, hardwood & pine floors, and a sweet porch all blend into a wonderful vacation spot....
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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, Sleeps 8Quick View
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    About this property
    All newly remodeled and furnished and tucked away on a quiet Oak Bluffs lane for the perfect reprieve after a day at the beach and shopping in town, along the Oak Bluffs harbor - and all just a short drive or bike ride away. This vacation home looks and feels so comfortable when you first walk in....
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 4Quick View
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    For those who love an in-town location this area known as the Campground with the historic Tabernacle is the ideal location. The sweet and colorful cottage is pristinely maintained by the owner. Rockers line the porch for your outside enjoyment. The main level hosts the living room with TV ( not...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, Sleeps 4Quick View
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    About this property
    Walk to Oak Bluffs town center, ferry or Inkwell Beach from this beach-chic recently renovated and adorable cottage. Upon entering you are greeted with an open floor plan in the living kitchen and dining areas. The living room is tastefully and comfortable furnished and has a 42" flat screen TV....
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, Sleeps 8Quick 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, Sleeps 8Quick View
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    About this property
    Beautiful Meadow View Farms home, bordered by expansive landscaped yard, peaceful private setting. Association tennis courts just a short distance from the house and Farm Neck Golf and Tennis is just a half mile from the house. Miles of connecting bike paths begin at the entrance to this lovely...
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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, Sleeps 8Quick View
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    About this property
    A recent renovation has moved this home to the top of the list in terms of comfort in a tastefully decorated waterfront home. A new family media room has been added giving extended families lots of space to relax. The open concept kitchen, dining and living areas feature waterviews and open onto a...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 5Quick View
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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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    Lovely cape home, all newly refurnished for 2013. First level features an open floor plan in the Dining, Kitchen and Living area. The tastefully decorated living area features comfortable furnishings and a 36" screen tv. One bedroom with a double bed and a full bath complete the living level. 2nd...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    About this property
    Amenities and Features include... Meadow View Farms, Out of Town, Association Tennis, Hi Speed Internet Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, food processor, washer / dryer, cd player, landscaped, outside shower - enclosed, outdoor...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    Enjoy the charm of a Vineyard cottage with all the amenities of today. This 3 bedroom house has brand new furnishings for 2015. It is in a quiet neighborhood not far from Oak Bluffs center and its harbor. The house is also close to the bike path. The house has an open floor plan with a large...
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    Oak Bluffs, Martha's Vineyard 02539
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 7Quick View
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    About this property
    Situated on quiet side street with a 15 minute walk or a 5 minute drive to town and beach, this light filled cape offers visiting families a well equipped vacation reprieve featuring comfortable living areas with mini split A/C and a modern spacious kitchen The first level features an open floor...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, Sleeps 8Quick View
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    • Grill
    • 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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Review
    5 Bedrooms, Sleeps 13Quick View
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    About this property
    Newly renovated 5 bedroom home just a mile and a half from the center of Oak Bluffs. New hard wood floors throughout as well as updated furnishings and decor. Dining area is extended by a nice sized sunny deck for outdoor dining. Perfect for a large family vacation. Additional amenities include:...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    2 Bedrooms, Sleeps 6Quick View
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    About this property
    A new Cape style residence 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 lead out onto a nice...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    Nestled in a private location on Crystal Lake which abounds with bird life, this is a delightful, vintage 1950's home with modern conveniences and comfortable furnishings. Its rambling single story layout is spacious and conducive to relaxed living. It is very well maintained and well equipped. The...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    About this property
    Walk to the beach! Walk to restaurants and shopping! Walk the kids to the arcade, Flying Horses Carousel, and lots of ice cream! Stay at a beautiful and bright home in the Historic Copeland District in Oak Bluffs. This 1928 home is mere minutes from dining and shopping on Circuit Avenue and the...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, Sleeps 10Quick 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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    3 Bedrooms, Sleeps 6Quick View
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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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 4Quick View
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    About this property
    This Seaview condo in Oak Bluffs has a lot to offer. You can walk to the beach and town and also enjoy beautiful waterviews from the patio. This unit is on the first floor with two bedrooms and two bathrooms. There is an open kitchen and living room with big windows that look out into the ocean....
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    Come experience the magic of the Vineyard in our island home. Modernized in 2011, this charming residence is clean, cozy and boasts new furniture and decor. Amenities include 3 TV’s, cable television, Wi-fi, DVD, telephone, I-home, and Keurig Coffee maker. The property has a private yard, sundeck,...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    Quietly nestled on quiet street just on the outskirts of town, this brightly lit home features a mix of coastal details and traditionally styled upscale furnishings for your comfort. The interior has open floor plan that flow nicely to outdoor living spaces including a screened porch and brick...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 4Quick View
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    About this property
    This sweet, little (it's priced accordingly!)cottage is all about convenience. It is within walking distance to the center of Oak Bluffs and two town beaches. The interior of the cottage has recently been redone inside and is fresh & clean and perfect for a great vacation. Large decks, lovely...
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    Oak Bluffs, Martha's Vineyard 02539
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, Sleeps 9Quick View
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    About this property
    Lovely spacious 3+ bedroom, 3.5 bedroom home within a mile from Oak Bluffs Center and beach area. Fully furnished screen porch. This home has been tastefully furnished throughout and will sleep families of 9 comfortably. Amenities and Features include... Stylish New Home, Central AC, Wifi,...
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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, Sleeps 6Quick View
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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....
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 7Quick View
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    About this property
    Bright, airy contemporary home located in the wonderful East Chop neighborhood. The first floor features an open concept living room and kitchen. The kitchen has a large island that can seat seven. First floor bedroom is located off of the living room and has access to the full bath. The second...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, Sleeps 8Quick View
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    About this property
    This charming home is situated in an idyllic private wooded setting on Sengekontacket Pond, one of the largest salt-water ponds on Martha's Vineyard. Comfortably furnished, it has a newlyr renovated kitchen and a new dining area overlooking Major's Cove. There is also a new screened in sun room for...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 7Quick View
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    Wonderfully located in the Meadow View Farm neighborhood this, four bedroom home offers easy access to downtown Oak Bluffs and Edgartown. The main floor offers an open dining area and living room with cozy fireplace for the cold fall nights. There is also one first floor bedroom and full bathroom...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    About this property
    Beautiful four bedroom house in the prestigious Farm Neck area overlooking a lovely lawn to a large tidal pond. This home offers an open floor plan so the whole family can be together. The kitchen and living areas open up to a wonderful deck so you can enjoy the views of Sengekontaket Pond....
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    7 Bedrooms, Sleeps 14Quick View
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    About this property
    Large families looking for a true shore experience will enjoy this delightful,whimsical, large historic summer home with cottage details set on the edge of Harthaven Harbor. The home boasts spectacular views of Vineyard Sound from all areas of the home. Private path leads you to a pristine private...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 14
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    5 Bedrooms, Sleeps 10Quick View
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    Smoking allowed
    About this property
    NEW LISTING FOR 2017 SUMMER! Beautiful main house and guest located a short walk to a private association beach on Lagoon Pond. The main house has three bedrooms and the guest house has two bedrooms. The main house has nice open feeling with with cathedral ceilings in the living and dining room...
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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, Sleeps 10Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    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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    4 Bedrooms, Sleeps 8Quick View
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    • Satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Come and enjoy this three level contemporary home with a beautiful landscaped yard. There is a wonderful deck off the kitchen with outdoor dining and seating area. the first floor offers and open kitchen, dining and TV/living room area. The is a second sitting room on this floor as well. The...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 6Quick View
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    About this property
    Modern two bedrooms, one bath cottage situated at the end of a quiet street. This cozy cottage is Oak Bluffs center and the town beaches. The home has recently been renovated with new comfortable furnishings including linens and mini spit air located about one mile to shops, restaurants in...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Pet friendly
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    Smoking allowed
    About this property
    Charming Gingerbread Cottage located in the Tabernacle area of Oak Bluffs. A short stroll brings you to Oak Bluffs Center with shops, family and fine dining, harbor area, bandstand park, and Ink Well Beach. Recently updated, this house features a modern eat in kitchen opening to the back deck and...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    5 Bedrooms, Sleeps 8Quick View
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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 in one direction and town center in the other, where you will find shops, eateries,- gourmet and family style, entertainment, the historic Flying Horsed Carousel, and the beautiful harborfront area....
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 5 Bedrooms, 1 Bathroom, Sleeps 8
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    6 Bedrooms, Sleeps 12Quick View
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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, Sleeps 6Quick View
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    Pristine 4 bedroom waterfront hideaway. Enjoy spectacular views and sunsets across the lagoon. Private dock for boat enthusiasts. Kayak and boat rentals can be delivered to the property and kayaking on the lagoon is a fun and picturesque activity for the entire family. Centrally located, you are...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, Sleeps 12Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming six bedroom home located within walking distance to town. The first floor has a nice living room/dining area with doors that open to the front porch. There are two bedroom and one full bath on the first floor too. The second floor has four additional bedrooms and two bathrooms. There...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, Sleeps 6Quick View
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    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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    2 Bedrooms, Sleeps 5Quick View
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    • Grill
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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...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and enjoy the newly renovated two bedroom home in Oak Bluffs. The first floor which is done in bright coastal colors has a nice eat in kitchen with a couple steps up to the living room with a large flat screen TV. The first floor also have a half bath. The second floor has two bedrooms and...
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    Location Information
    Oak Bluffs, Martha's Vineyard 02577
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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