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Holiday Rentals and Homes in Oak Bluffs, MA

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    Travellers to Oak Bluffs are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    6 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    4 of 5 stars (1) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 13 | Quick View
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    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:... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 12
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    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... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 19
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This unique and elegant four bedroom beach cottage is situated on the north shore of Martha's Vineyard. For your relaxation, there is a large porch/patio leading out to the beach affording magnificent views. Additional views from the tastefully decorated living area, bedrooms areas, make this a... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 27
    5 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    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.... 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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    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
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    Oak Bluffs, Martha's Vineyard
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
    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 02557
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    1 / 23
    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
    1 / 33
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick 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... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 20
    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
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick 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... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 30
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    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
    1 / 20
    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
    1 / 5
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Central Heating
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    • x
    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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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Great Getaway Cottage with a short walk to Circuit Ave, the harbor, and the Lagoon .A back yard w/ picnic table, BBQ grill. About a mile walk or bike ride to Town. The house has hardwood and fir floors throughout and also has air conditioning. This is a great "get away cottage" for a small family... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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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.... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Porch
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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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    1 / 8
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
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    • x
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    About this property
    A fully renovated four bedroom home with 3 1/2 baths, family room, landscaped lot and a private beach and dock. Dock can accommodate up to a 25 foot motor boat, located on The Lagoon and is accessible to Vineyard Sound. Family room has cable TV, deck, fully equipped kitchen, and a 2 person kayak... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 26
    6 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    Enjoy Oak Bluffs summer living at its best in this wonderful family home. Located in desireable East Chop. Walk to town and beach. Amenities and Features include... Classic East Chop Summer Home, Wifi Internet Additional amenities include: beach chairs, coffee maker, outside shower - open,... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 25
    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Renovated beach house in Oak Bluffs with 5 Bedrooms, 2 full baths, Sleeps 8; Large living/dining room, sliding door opens to deck, flagstone picnic area with gas grill, A/C, Washer/Dryer, Free WIFI, Large flat-screen LED TV's with cable service; Located 10-20 min walk to Oak Bluffs harbor, beach... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This gorgeous, contemporary air-conditioned private home is perfect for your luxurious vacation on the island. It is 2700 sq ft of well laid-out space and sits on 1.4 acres of land in a private wooded area, centrally located, only minutes from downtown Oak Bluffs and beautiful beaches. The... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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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    Oak Bluffs, Martha's Vineyard
    1 / 17
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    10 minute walk to Oak Bluffs center and beach area from this lovely modern vacation home. Enjoy all that the summer community of Oak Bluffs has to offer, quaint shops, fine and family dining, harbor front stroll where you will and array of dining establishments, all waterside, boat rentals and... 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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    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... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 20
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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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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    Oak Bluffs, Martha's Vineyard
    8 Bedrooms, 8 Bathrooms, Sleeps 20 | Quick View
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    • Hot Tub
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    • Terrace
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    • Balcony
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    About this property
    Amazing five acre property! 6 BR main house w/ pool + a 2 BR carriage house! Our amazing property is perfect for everything from a memorable family vacation to a serene retreat. You and your guests will begin to enjoy the feeling of privacy the minute you arrive as you drive down the long tree... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 23
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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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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    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our picture-perfect home is an excellent summer escape. Spacious double lot makes this setting seem like a parkland. It's just a 15-minute walk to downtown Oak Bluffs and the town beach. It's also on the public transit line and the bike path. View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 10
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities and Features include... Private Pool, High 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 furniture, ironing board. View all property information
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    Oak Bluffs, Martha's Vineyard
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    3 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
    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
    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
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • ?
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    This classic Gingerbread House is less than a block away from the beach in Oak Bluffs. Surrounded by parks in a residential neighborhood, the property is easy walking distance to shops, restaurants, harbor, galleries, etc.. This house is spacious with high ceilings and over-sized rooms. The... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 15
    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 / 29
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Soak in one of the loveliest sunset views on Martha's Vineyard when you escape to this two-bedroom Oak Bluffs cottage, where you'll enjoy a short walk to the ferries and a private deck with panoramic views of Lagoon Pond, Brush Pond, Vineyard Sound, and Vineyard Haven. This single-level cottage... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    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
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • DVD Player
    • Grill
    • Outdoor Dining Area
    • Parking
    • Washer
    • Wi-Fi
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This airy home captures the spirit of easy island life and makes you feel like you've gotten away. It's secluded on a quiet, wooded, paved, dead-end street, the second house from the end. Yet it's centrally located in the East Chop area of Oak Bluffs for easy access to the beaches (.25 miles to... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    5 Bedrooms, 4 Bathrooms, Sleeps 22 | Quick View
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    • Hot Tub
    • Satellite TV
    • Washer
    • Patio
    • Grill
    • Internet Access
    • Private Outdoor...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 14
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Satellite TV
    • Grill
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This home is Oak Bluffs at its best - close to town but tucked away off a main street, the house is truly a beauty with special, thoughtful details and wonderful furnishings. The new home has the yummiest colors with a handsome, soft blue master bedroom and bath, a twin bedroom in warm gold, one... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    1 / 36
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • Grill
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Oak Bluffs retreat featuring three levels of luxury living, professionally decorated by one of the islands premier decorators This house is privately situated in an enclave of lovely homes. Bike paths at the entrance connect to miles of biking trails. Farm Neck Golf Course and Restaurant are just a... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 24
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Patio
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Escape to the perfect island getaway at this gorgeous, recently renovated Oak Bluffs home on lovely Martha's Vineyard. Light-filled bedrooms, a playroom, and a huge deck await! Downtown Oak Bluffs is nearby and it's only one mile to the water. If you'd rather remain on the property, you're... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 23
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Porch
    • Grill
    • Air Conditioning
    • DVD Player
    • Patio
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 38
    5 of 5 stars (6) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Internet Access
    • Grill
    • Satellite TV
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    • Waterfront
    • DVD Player
    • Air Conditioning
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    1 / 16
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This grand Victorian jewel on Ocean Park has been completely renovated and transformed into a beautiful vacation home. Enjoy water and park views from inside this elegant home, the expansive wraparound porch and the second floor balcony. This beautifully restored Victorian home is a rare find... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Porch
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Amenities and Features include... Additional amenities include: beach chairs, coffee maker, patio table and chairs, lobster pot, washer / dryer, landscaped, outside shower - enclosed, vacuum, outdoor furniture, ironing board. View all property information
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    Oak Bluffs, Martha's Vineyard
    1 / 18
    5 of 5 stars (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • Parking
    • Outdoor Dining Area
    • Grill
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This spacious condo is an ideal vacation rental for a small family, a couple or two couples looking for clean, comfortable accommodations with the amenities needed to ensure a relaxed vacation. This large 2 bedroom end unit (1200 sq ft + large deck) is bright and airy. Downstairs has new hardwood... View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard 02557