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Oak Bluffs Summer Rentals

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    Travellers to Oak Bluffs are booking June dates now. Secure your holiday rental today, and have the perfect trip.
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    4 BedroomsSleeps 8Quick View
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    Amenities and Features include... Hidden Cove, Centrally Located to Beaches and Towns, Association Tennis Courts, A/C, WiFi Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, landscaped, outside shower - enclosed, vacuum, outdoor...
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    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 BedroomsSleeps 4Quick View
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    Amenities and Features include... Walk to Town and Beach, Newly Renovated Additional amenities include: coffee maker, patio table and chairs, lobster pot, washer / dryer, landscaped, outdoor furniture, ironing board.
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 BedroomsSleeps 9Quick View
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    About this property
    Sea breezes and fabulous water views from almost every room are the mainstay for this unique waterfront home on the Lagoon Pond in Oak Bluffs. Polished with soothing designer furnishings in layers of cappuccino and white neutral linen and cotton, you will enjoy this European-chic interior almost as...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 BedroomsSleeps 8Quick View
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    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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 BedroomsSleeps 10Quick 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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 BedroomsSleeps 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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    4 BedroomsSleeps 8Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    About this property
    Note: New for Summer 2017, In ground heated 18 x 30 pool, patio dining table and 6 chaise lounge chairs. Depth of pool 3.5 to 6 feet. Oak Bluffs retreat featuring a pool, outdoor patio, spacious dining deck and three levels of luxury living. The outstanding home has been professionally decorated by...
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    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 BedroomsSleeps 4Quick View
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    About this property
    European-styled cottage is tucked away down a private lane surrounded by private yard with gardens - you’ll feel like you have completely gotten away from it all. The front door opens into a classic Mudroom with an antique wood, stadium bench seat - and then you step into the open and airy Great...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 BedroomsSleeps 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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    2 BedroomsSleeps 4Quick View
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    About this property
    Adorable Waterfront and Beachfront cottage. Immaculately maintained, lots of summer charm, fantastic views of the Vineyard Sound and Lagoon from the large patio area. Stairs lead directly to private, sandy beach, great area for young children and adults. Kayak enthusiasts will enjoy this waterfront...
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    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 BedroomsSleeps 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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    4 BedroomsSleeps 8Quick 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......
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 BedroomsSleeps 6Quick View
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    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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    1 BedroomSleeps 3Quick View
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    About this property
    Tiny beach cottage, a rare find these days and just perfectly cute. The cottage is located along the waterfront on East Chop Drive, a very desirable area of Oak Bluffs. The porch looks out over the beach and beyond to the Vineyard Sound. Relax on the covered porch and take in the outstanding...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    7 BedroomsSleeps 14Quick View
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    • Waterfront
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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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    3 BedroomsSleeps 6Quick 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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 BedroomsSleeps 6Quick View
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    • Grill
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    Pet friendly
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    About this property
    Little Jaws, the home where the movie Jaws was filmed is a pristine beach cottage. Set in East Chop, this three plus bedroom rental offering features spectacular views, great swimming, kayaking and gorgeous sunsets. Relax on the large and comfortably furnished waterfront veranda. The living room...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 BedroomsSleeps 7Quick View
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    • Grill
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    • Waterfront
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Architect designed, luxury waterfront retreat. This unique home sits overlooking 500 feet of private lagoon beach and maintains sweeping waterviews up the lagoon. The pool and patio areas feature outdoor dining, sectional sofa seating, lounge area, and a hot tub all taking full advantage of the...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    4 BedroomsSleeps 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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    1 Review
    3 BedroomsSleeps 6Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    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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    5 BedroomsSleeps 8Quick View
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    • Satellite TV
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    • Private Outdoor Pool (Unheated)
    • DVD Player
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    Pet friendly
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    Smoking allowed
    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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    5 BedroomsSleeps 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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    4 BedroomsSleeps 7Quick 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...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 BedroomsSleeps 4Quick View
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    About this property
    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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    6 BedroomsSleeps 13Quick View
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    About this property
    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 BedroomsSleeps 12Quick View
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    About this property
    Privately situated on a hilltop in Sengkontacket, -spacious tri-leve 4000 sq ft contemporary home. This wonderful vacation home has been updated for summer 2015, AC added, freshly painted, new carpeting and hardwood flooring and new furnishings. Set in a wonderful family friendly community offering...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    4 BedroomsSleeps 8Quick View
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    Spacious and attractive waterfront Cape Cod style home - features gorgeous views, central A/C, Wi-Fi and 4 TV's. Two large decks and a screened porch provide wonderful spaces for summer relaxation in which to enjoy the waterviews. Kayaking enthusiasts will enjoy the gorgeous scenery and wild life...
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    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    About this property
    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 living level features an open concept and hosts a family TV room and luncheon breakfast nook,...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 BedroomsSleeps 6Quick View
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    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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 BedroomsSleeps 5Quick View
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    About this property
    Families are sure to enjoy this cozy home with nautical inspired decor. The main living level offers a spacious living and dining area with cathedral ceiling cooled by window AC. and a neat well equipped kitchen with pass through window. The kitchen opens onto a spacious deck with patio dining and...
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    Oak Bluffs, Martha's Vineyard 02536
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    6 BedroomsSleeps 12Quick View
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    About this property
    Large families looking for a beachfront adventure will love this relaxed waterfront home. Spectacular views from every room and expansive patios stretch the shoreline. Central location offers a 5 minute drive to town, dining, movies, shops and galleries. Amenities and Features include......
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    1 BedroomSleeps 2Quick View
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    About this property
    Cute and Cozy guest house with open floor plan in the kitchen, living and alcove sleeping area with queen bed. This cottage is perfect for couples, the owner will consider one additional child. There is a den with futon sofa separate from the main part of the cottage. Relax on the deck while you...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 BedroomsSleeps 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 BedroomsSleeps 12Quick View
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    About this property
    Welcome to "Shangrila" A beautiful townhouse condominium end unit with magnificient views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 BedroomsSleeps 6Quick View
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    About this property
    Picturesque ocean views across Farm Pond to Vineyard Sound. Walk to beach and town. Bike path is one block away from this beautifully renovated three bedroom, two bathroom home. Open, airy with lots of glass. The dining and living areas open to deck. Amenities and Features include... Farm Pond...
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    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Wi-Fi
    • Waterfront
    • Ocean Views
    • Air Conditioning
    • Parking
    • Washer
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious gingerbread directly across from Union Chapel. Sit and watch the action roll by from the comfort of large front porch or enjoy the quiet and private yard/patio on the side of the house. Even though there are 3 parking spots on the premises the location affords you the luxury to easily walk...
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    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 BedroomsSleeps 6Quick View
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    • Internet Access
    • Satellite TV
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amenities and Features include... Hidden Cove, Association Tennis Courts, Association Kayak Landing Additional amenities include: coffee maker, fans - portable, lobster pot, food processor, washer / dryer, porch - screened, vacuum, outdoor furniture, tennis - association/shared, ironing board.
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    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 BedroomsSleeps 8Quick View
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    • Satellite TV
    • Internet Access
    • Patio
    • DVD Player
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 BedroomsSleeps 6Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 6
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    7 BedroomsSleeps 14Quick View
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    • DVD Player
    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In Town, walk to beach, tennis and town area. This wonderful family home has a large wrap around porch, 7 bedrooms and sleeps 12-14. Many areas of this wonderful older home have been updated. Hi Speed Internet. Amenities and Features include... 1 Block to Beach, Wifi Internet, Linens Provided,...
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    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 14
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    4 BedroomsSleeps 8Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 BedroomsSleeps 6Quick View
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    • Air Conditioning
    • Satellite TV
    • Patio
    • Grill
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    3 BedroomsSleeps 4Quick View
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    • Air Conditioning
    • Grill
    • Waterfront
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 BedroomsSleeps 7Quick View
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    • Air Conditioning
    • Grill
    • Satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Delightful summer cottage. Great family home for relaxing on the large deck, kayaking the lagoon, great play beach on the lagoon for children. The bunk house with two bedrooms is directly behind the main part of the house, about 10 steps across the yard. The views are spectacular and expansive....
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    Oak Bluffs, Martha's Vineyard 02536
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    6 BedroomsSleeps 11Quick View
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    • Satellite TV
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amenities and Features include... In-Town, Walk to Beach, Wifi Internet Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, cd player, landscaped, outside shower - enclosed, outdoor furniture, ironing board.
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    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 11
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    4 BedroomsSleeps 8Quick View
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    • Grill
    • Waterfront
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 BedroomsSleeps 6Quick View
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    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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