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Pet Friendly Holiday Rentals in Oak Bluffs

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    1 / 17
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    5 of 5 bubbles (2) Excellent
    6 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 22 | Quick View
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    About this property
    This upscale, newly renovated, 4 bedroom home in a quiet neighborhood in Oak Bluffs. You are 2.5 miles from the town center and Inkwell and State beautiful public beaches. This home boasts a large unground back yard pool and hot tub on the mahogany deck. Large outdoor shower. Grill and fire pit... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 5
    4 of 5 bubbles (3) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Central Heating
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    About this property
    This 4 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
    5 of 5 bubbles Reviewed 9 September 2016
    Before choosing this property, I referenced other review sources (i.e., AirBnB) and am glad I did. I found the property to be a great find: well appointed, nestled in a quiet...
    5 of 5 bubbles Reviewed 8 September 2016
    Family members from CT, MD, NJ and NY gathered here for the Labor Day weekend. It was vary comfortable, convenient to downtown and quiet. 4 bedrooms and a pull out couch for the...
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    1 / 22
    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This bright and charming 3 bedroom, 1.5 bath house rests outside downtown Oak Bluffs. The house boasts 3 bedrooms, 1.5 baths, an open living room/kitchen combination, 2 decks and an outside eating area. The first floor bedroom contains a full sized bed. A half bath with laundry is across the... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    5 of 5 bubbles Reviewed 20 July 2015
    We stayed here with three adult sons and one son's wife so the total was six. .We were here for 4th of july week. This house has a great layout. It has three good size bedrooms...
    5 of 5 bubbles Reviewed 26 June 2015
    This is an excellent house for rent at a good price point. The home is modern and well maintained. It's about 1.5-2 miles from downtown Oaks bluff. I walked a couple of times to...
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    1 / 17
    4.5 of 5 bubbles (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Private Garden
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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
    4 of 5 bubbles Reviewed 16 July 2016
    My family and I had a great vacation at Summer Home - By the lagoon. The property is located on a quiet street but, centrally located to downtown Oak Bluffs and other popular...
    5 of 5 bubbles Reviewed 13 June 2016
    This perfect summer rental is perfectly located to all the main locations. You are only minutes from downtown Oak Bluffs and Circuit Ave. The other direction you are minutes from...
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    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our comfortable, reverse contemporary home has 2 bedrooms on the first floor (one with a full size bed and one with a twin), a 3/4 bath with shower, as well as a family room with a fold-out futon couch. Upstairs on the second floor, our home has an open design with a bright kitchen/dining/living... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    4 of 5 bubbles Reviewed 26 August 2016
    My stay at the house was very good and the photos were true to the accommodations. I thought there were 2 twin beds in one of the rooms but it was ok since the downstairs den had...
    5 of 5 bubbles Reviewed 14 April 2016
    Location, location is perfect for getting to town, beach and other parts of MV! The house is right size for family of 4. The owner is very responsive and the house was well...
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    1 / 17
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    About this property
    This is an old farmhouse consisting of 2 floors with 3 bedrooms on the second floor and 1 on the first floor. One queen and 3 doubles. A large living room and bath on the first floor. In the kitchen is a Refrigerator, gas stove with oven, a washer and dryer and a dishwasher. There is a portable... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    5 of 5 bubbles Reviewed 23 August 2014
    So often descriptions fall short of reality but our stay at this Flip-key rental was as it was toted, a "Charming Farmhouse." The four bedrooms were sweet and spacious decorated...
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    1 / 7
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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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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    1 / 44
    2 of 5 bubbles (1) Poor
    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    *Fall/Winter/Spring multi-week discount available *Only 1 prime summer week left! Check my calendar and book ASAP if you plan to visit in the peak season. *Perfect location so No Car Needed. Easy walk to town, beach & parks. The Pennacook house in Oak Bluffs on the charming island of Martha's... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Come and let your cares float away as you relax on the enormous first-floor front porch or second-floor open deck of this charming 100+-year-old home looking out onto the beautiful Nantucket Sound. The home is sunny, bright and spacious and has a relaxed elegance with a large open living room... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Sea Glass Cottage Martha's Vineyard Vacation Rentals Sleeps 6. Completely renovated, this charming East Chop cottage will allow its guests to experience all the comforts of modern luxury living combined with the historical splendor of many reclaimed antique furniture pieces from Martha's Vineyard... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    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... View all property information
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    Oak Bluffs, Martha's Vineyard 02577
    1 / 21
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Completely renovated cottage in the Sunset Lake area of Oak Bluffs. Walk to town and library. Completely renovated modern kitchen. Rock away on the large front porch. Additional amenities include: games, coffee maker, outdoor shower, lobster pot, cd player, wine glasses, fans, vacuum, washer &... 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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    Beautiful four bedroom home within walking distance to the Oak Bluffs harbor and town. This home has a nice size first floor living room and separate eat in kitchen. The first floor also has a full bathroom with tub and shower. The second floor has four bedrooms and one full size bathroom. The... 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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    • Grill
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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
    1 / 17
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    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... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Stay in this peaceful, well-maintained home with a large wrap-around porch, a deck, and in close proximity to the ocean for your next unforgettable New England vacation. Come with a small group of friends, bring your own small family, or get away with another couple and rest assured that you'll... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick 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... 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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    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... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    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: coffee maker,... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Waterview Farm boasts views across peaceful meadows to Sengekontacket Pond and beyond. Launch canoes and kayaks at private association beach on the pond. Great location for families. Close to bike paths, town and beaches. House has an open, airy floor plan and large deck. Amenities and Features... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 22
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    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
    1 / 16
    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Wonderful home located about a 10 minute walk to downtown Oak Bluffs. This home has a nice open floor plan for family gatherings, updated furnishings, fully equipped kitchen with stainless steel appliances, Master bath Jacuzzi tub, Entertainment systems include flat screen TVs, CD, DVD, VCR,... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    About this property
    JUNE & JULY RATES REDUCED!!<BR><BR>You will be within walking distance from downtown shopping, movie theatre, restaurants, bike path, harbor, beaches, and two-tenths of a mile from the brand-new modern library.<BR><BR>Relaxed and warm, this brand-new home is expertly decorated. The open floor plan... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick 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... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 11
    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    About this property
    New Renovated, 1870 historic "Campground" cottage centrally located in Oak Bluffs, The cottage has 4 bedrooms (all located on the second floor) - 1 queen, 2 double beds and 2 twins beds. The front bedroom has its own balcony with water views. Cottage sleeps 8. the first floor includes a newly... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 14
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick 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,... 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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    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
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Home away from Home! Walk to Sailing Camp! Bright, sunny 3 bedroom Cape style vacation home in Lagoon Heights with great amenities. Fully furnished home with 2 baths, outdoor shower, large deck and private enclosed yard and a wonderful deck for the summer cookouts. Open floor plan with spacious... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 21
    4 of 5 bubbles (1) Very good
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    This well maintained, vintage Victorian home is centrally located, yet away from the hustle and bustle of town: just one block from the beach, two blocks from Waban Park and Ocean Park, three blocks from tennis, backetball and a playground and four blocks from town. Enjoy the waterview of Vineyard... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    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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    Oak Bluffs, Martha's Vineyard 02539
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Views, Views and more Views! Lovely water views of Sengekontacket Pond over the rolling "forever" conservation land. Large contemporary home has been recently updated to 4 bedrooms and 3 full baths. Large open living space with deck overlooking the view and sun room. Access to association dock and... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 22
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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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 9 | Quick View
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    This fabulous 125 year-old Victorian cottage was lovingly updated and completely restored in 2012. Sitting on a large private lot, just steps from Inkwell beach, Solera offers the perfect balance of comfort, ambiance and vintage charm. The large, airy gourmet kitchen was featured in This Old House... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
    1 / 20
    5 of 5 bubbles (59) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • DVD Player
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    This Oak Bluffs, Martha's Vineyard rental is a certified National Historic Property. Ideal location for visitors in the middle of the most active, multi-cultural, charming, and fun town on Martha's Vineyard. Step outside your door for breakfast or ice cream, a great selection of restaurants in... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    5 of 5 bubbles Reviewed 14 November 2016
    This rental is the best place to stay for our family. We've been returning every year to stay at the Historic Arcade Building for about 8 years. The location is perfect, walking...
    5 of 5 bubbles Reviewed 11 October 2016
    We have been staying at this apartment for years now. We look forward all year to going back to the same place. We now have come to refer to it as home! We love the location as it...
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    1 / 16
    3 of 5 bubbles (2) Average
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Terrace
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    • 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 in some rooms, parking. Overlooking a park, sip your coffee on the... 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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    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.... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 22
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Just a block from the East Chop Bluffs on a sleepy side street in a quiet wooded setting. There are 2 SEPERATE LIVING ROOMS!! Large bright kitchen that accesses a separate dining room, inviting screen porch with dining and sitting areas, and sunny rear deck with lots of backyard privacy. Ocean... View all property information
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    Oak Bluffs, Martha's Vineyard 02257
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    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    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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    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
    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... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    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... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 22
    4 of 5 bubbles (2) Very good
    8 Bedrooms, 3 Bathrooms, Sleeps 16 | Quick View
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    A true Vineyard classic from 1890, this house retains its authentic charm yet has been thoughtfully renovated and serves the modern day vacationer well. The 8 bedrooms afford plenty of space to accomodate larger family groups for special reunions and vacations. The living room, sunporch and kitchen... 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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    • x
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    About this property
    Spacious contemporary 4 bedroom 3.5 bath home located in one Oak Bluffs most exclusive neighborhoods. This house offers many features such as hardwood floors, central air conditioning, and a large living dining area with walk out deck and patio. The yard is nicely landscaped with waterviews over... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 40
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Terrace
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    • Internet Access
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    This classic Oak Bluffs home is filled with antiques and has views of the pier from the front porch. It's the perfect home for families wanting a relaxing getaway. This historic cottage is only five minutes away from Ink Well Beach and the Steamship Authority Dock, and is just a half mile from the... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 14
    5 of 5 bubbles (3) Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    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.... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557