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Oak Bluffs Holiday 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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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Wonderful Oak Bluffs home close to town and beach. This home has an open floor plan which is nice for relaxing with family and friends. There is one master bedroom on the 1st floor with a bath. The three additional bedrooms are on the 2nd floor. There is a master bedroom with a private bath and...
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    Oak Bluffs, Martha's Vineyard 02539
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    This convenient first-floor studio is ready and waiting to make your Martha's Vineyard vacation memorable with a shared pool and tennis, as well as easy access to the beach. And it's dog-friendly, too, so bring along your canine family members for a small nightly fee! You'll be situated in the...
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    6 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    Come and enjoy this beautiful waterfront home on East Chop! The first floor has a wonderful front seasonal porch with views of the Vineyard Sound. There is a large dining table and room to relax and take in the view. There is also a living room that leads into the kitchen on the 1st floor. The...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    About this property
    The Blue Canoe is completely fresh and renovated, while its 1910 charm is fully intact. It has a lovely deck and a huge side yard surrounded by a split rail fence just perfect for enjoying summer lounging and games. The house is in a neighborhood central to many things including being just steps to...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
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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...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    If it's time for your next getaway to Martha's Vineyard, make this dog-friendly studio-style condo your home away from home, and enjoy a shared pool and tennis, as well as close proximity to the beach and golf. Golfers will be pleased to be staying right on the edge of the Farm Neck Golf Club....
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Welcome to Martha's Vineyard all people, local/foreign/happy/LGBT/Spiritual-not! Our home is located across from Norton's Farm and public transportation. Car and motorbike are best to access everything from this location. The twin room contains two single beds, great for teens, traveling...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    You'll find all you need and more for your next vacation at this lovely two-level townhouse on Martha's Vineyard. Relaxation is never far away with a shared swimming pool, tennis courts, and an easy stroll to the beach! The family dog is also welcome to join you here for an additional nightly fee....
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Historic harborfront home with private dock has been completely renovated and newly furnished, beautifully appointed throughout to reflect summer living on the Vineyard. The large living and dining areas open onto the expansive and comfortably furnished porch, overlooking picturesque Oak Bluffs...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    The Circle on Martha's Vineyard is a quaint vacation hide-away with all the comforts of home where you can enjoy quiet mornings on the deck with a cup of coffee or book. The Circle is a short walk into town where you can enjoy shopping, sightseeing or a nice afternoon lunch or maybe enjoy a bike...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Four bedroom Oak Bluffs home located in the Waterview Farm area of Oak Bluffs. Adjacent to Farm Neck Golf & Tennis. Access to Sengekontacket pond. Great for kayaking and canoeing. Large house great for an extended family or two small families. The first floor has an open concept living room,...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Whether you're lounging on the lawn next to the shared pool or curled up with a book in the bright living room, you'll love your stay at this dog-friendly first-floor condo in the Island Inn at Martha's Vineyard community. Bring your tennis rackets along for a match on the grounds' shared courts,...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    About this property
    Historic summer 'cottage' with 7 bedrooms, sleeping porches, a deck overlooking the water, a private dock on Harthaven Harbor, and immediate access to the ocean. The rustic home is a perfect gathering spot for family and friends. It has a large living room with a huge stone fireplace, an eat-in...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 14
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Head to Martha's Vineyard and make this dog-friendly, studio-style condo for your home base and enjoy a stress-free vacation complete with a shared pool and tennis and easy access to golf and the beach. If you love the beach, you'll be able to get there on a moment's notice with Joseph Sylvia...
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Sprawling Oak Bluffs home with five bedrooms and 3 full bathrooms. The home is located about a half mile walk to Oak Bluffs center and about a 1 mile walk or bike to the Inkwell Beach and close to Oak Bluffs Library. The first floor features open kitchen and dining/living room area along with four...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Settle into this cozy first-floor condo and prepare for a wonderful Martha's Vineyard getaway! You'll have access to the property's pool, kids' playground, grilling area, and more. The condo's interior, which includes a private bedroom and bathroom, is newly refurbished and feels like home. Stroll...
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    VINTAGE 1950'S HOME LOCATED ON CRYSTAL LAKE IN OAK BLUFFS1 / 19
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Nestled in a private location on Crystal Lake which abounds with bird life, this is a delightful, vintage 1950's home with modern conveniences and comfortable furnishings. Its rambling single story layout is spacious and conducive to relaxed living. It is very well maintained and well equipped. The...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Fulfill your dreams of a summer vacation on Martha's Vineyard at this deluxe townhouse suite at The Island Inn, where you'll enjoy a private deck, easy walking access to the beaches of Oak Bluffs, and shared on-site amenities that include a swimming pool and tennis courts. This two-level townhouse...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Tucked away on a quiet Oak Bluffs lane, just one mile from Oak Bluffs center, this Ideal vacation home with 3 bedrooms and two baths sleeps 7 and is the main house to a lovely two home main and guest house property. The interior has been completely renovated and features sun filled rooms, three...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Lovely Oak Bluffs home one mile from town and beach1 / 23
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    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...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    • Private Outdoor Pool (Heated)
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    About this property
    New to the 2015 Summer Season! This spacious waterfront home offers 4-bedrooms en-suite, with family, game and fitness rooms...and yes, a pool. The peaceful setting is centrally located, yet close to the village center for easy access to shops, restaurants and more. The home is tastefully...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Enjoy this perfect Oak Bluffs beach-styled house with views of stunning conservation land and waterviews across Sengetkontacket. This contemporary vacation home with air conditioning has just been update with a mix of new and shabby sheik furnishings, fresh carpet, and paint for the 2015 season....
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    Oak Bluffs, Martha's Vineyard 02536
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    7 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    Spacious Modern Vacation Compound, main and guest house providing 5 bedrooms, 3.5 baths and multiple living spaces. A short walk to a 25 ft right away leading to the lagoon, perfect for a morning swim and kayaking. The main house features a large great room combined living and dining area with...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Come fill your days with relaxation, beauty, and memory-making fun when you book your trip to this seaside Martha's Vineyard condo. Featuring shared amenities like a pristine pool, community tennis courts, and lushly landscaped ground, this vacation getaway offers up to four guests the chance to...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This wonderful family vacation home features lovely waterviews across Crystal lake. The peaceful location and large yard provide the perfect venue for extended families with children. Relax on the expansive deck, enjoy the views from the 4 person glider swing as seen in the photos Families will...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Treat yourself and your loved ones to an unforgettable Martha's Vineyard getaway with this charming Island Inn condo! With a broad range of amenities, including a shared swimming pool, three tennis courts, and a great location just half a mile to the beach, this lovely vacation rental is sure to...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    The Circle has served the island’s robust summer rental community for over 30 years providing guests with cozy accommodations with a Cape Cod feel. While sitting off the main road The Circle offers quiet mornings for reading on the deck or enjoying that first cup of coffee surrounded by abundant...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Gorgeous light filled vacation home, tucked away in a private community centrally located just minutes from Oak Bluffs, Edgartown and several beautiful beaches. Privately situated this home features multiple living areas, chef's kitchen and a spacious patio area with outdoor dining Upon...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    This home will be receiving the remaining new furnishings, art work, decor items, patio table and chair, additional outdoor seating such as chaise lounge chairs through March. Photos represent the house as of 1/24/18. Stylish, contemporary, light filled cape home has been completely renovated...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Searching for your family's new favorite Martha's Vineyard getaway? This first-floor Island Inn condo may be your answer. Access to the pool, tennis court, and grilling area means you'll never run out of ways to relax. Plus, this studio double's location near the shore and activities can't be beat....
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Whether you're looking for a romantic getaway or a relaxing New England retreat with a close friend, you'll love this second-floor suite at the Island Inn. Experience an amazing vacation in Martha's Vineyard, with amenities like a shared pool on-site and plenty of sightseeing in nearby Oak Bluffs....
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Coastal comfort awaits at this lovely Martha's Vineyard condo, tucked only a few minutes by foot or car to the island's famous beaches! And with amenities ranging from tennis to golf and a shared outdoor pool, there's no better way to treat yourself to a perfect getaway. Part of a beautifully...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
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    Smoking allowed
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    Show your special someone the relaxing New England retreat they deserve with this first-floor condo at the Island Inn at Martha's Vineyard! You'll enjoy a shared swimming pool, nearby golf, and easy access to shopping, dining, and the beach. You and your sweetheart will love exploring the...
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Oak Bluffs is the font entry way. The Inkwell Beach is the living room with a large flat screen TV with surround a sound and a dining area, the kitchen area with an island cooking surface it is where all the action happens this flat screen today. . The family room downstairs is named Chilmark...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This one-bedroom Martha's Vineyard condo features free WiFi, a furnished patio, fireplace, kitchen, and room for up to six guests. Visitors will also enjoy access to several on-site amenities including a shared outdoor pool, tennis courts, picnic area, and a children's playground. Golfers will be...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Oak Bluffs Rental - Walk to the Beach1 / 25
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 bedroom, one and a two half baths with an outdoor shower, is located on a quiet backroad in Eastchop, Oak Bluffs. Less than a 0.5 walk to the Oak Bluffs beach and to town (Circuit Ave). The house comfortably sleeps seven + adults: • Master bedroom with a queen bed (2) • Two bedrooms,...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Contemporary styling and newly updated 2 bedroom, 2 bath condominium in the heart of Oak Bluffs and just across the street from the beach. Spectacular views from the main living area, master bedroom and balcony areas. Stroll the waterfront past historic homes and parks to the center of the village...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make your next visit to Martha's Vineyard everything you hope for by staying in this charming two-level townhouse close to the beach! Not only will you have plenty of room for everyone to spread out, but you'll also enjoy access to a shared pool, deck, on-site tennis, and more! Please be aware this...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend an unforgettable summer on the beaches of Martha's Vineyard when you retreat to this two-bedroom townhouse, a charming Oak Bluffs escape with a private deck, a shared swimming pool and tennis courts, and easy walking access to downtown and nearby beaches. Please be aware this rental has a...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a romantic getaway to Martha's Vineyard at this adorable studio condo for two. With access to a shared swimming pool, tennis courts, and a picnic area, guests of the Island Inn will have a magical time at this rental. This first-floor studio is located along the edge of the highly rated Farm...
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gorgeous Three-bedroom, two and a half bath on a cul-de-sac with minimal traffic. Perfect share for 2-3 couples or a small family! Furnished/Beautiful screened in porch for outdoor dining, also equipped with an outdoor shower for post-beach cleanliness. Private setting in much-sought-after Hidden...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of East Chop is this custom built three bedroom cottage. The home features three bedrooms, three bathrooms and an open floor plan. The master bedroom is located on the first floor and there are two additional bedrooms on the second floor with a shared hall bathroom. Enjoy...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for couples or close friends, this second floor Island Inn condo is the ideal home base for exploring Martha's Vineyard! From the sights of Oak Bluffs to perks like a shared pool and tennis courts, you'll have everything you need to make your next New England getaway special. The family dog...
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get ready for a truly memorable vacation in Martha's Vineyard at this cozy studio condo within the wooded Island Inn community. During your stay, enjoy access to a shared pool, tennis courts, and a picnic and BBQ area. Take a short stroll over to the beach to watch the sunrise and then head north...
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Washer
    • Grill
    • Internet Access
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You and your loved ones deserve a peaceful getaway to one of the most breathtaking locales in New England. This first-floor condo at the Island Inn lets you make the most of Martha's Vineyard, with a shared pool, tennis courts, and nearby golf for when you return. A great location near the coast...
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fill your picturesque stay with stress-melting relaxation and beachside memories when you book your next retreat to this Martha's Vineyard studio. With on-site tennis courts, easy beach access, and a pristine community pool, this rental surrounds you with opportunities for fun and tranquility....
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
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