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Pet Friendly Holiday Rentals in Oak Bluffs

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    Travellers to Oak Bluffs are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    35 Matching Rentals in Oak BluffsView all 246 rentals
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    In-Town Historic Property on Martha's Vineyard1 / 20
    (71)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Charming house with lots of entertainment and gourmet kitchen!1 / 24
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Ocean, lake, harbor and parkview Vineyard cottage1 / 17
    (2)Excellent
    6 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
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    Island Inn - 43G You'll feel right at home when you stay at this Island Inn townhouse on Martha's Vineyard. Featuring access to a shared pool, tennis courts, and an easy walk to the beach, all you have to do is make the memories! Island Inn occupies a corner of the Farm Neck Golf Club, a short...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Charming, dog-friendly home away from home near Lagoon Pond w/ boat launch1 / 26
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
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    • Private Garden
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    Kid friendly
    Smoking allowed
    Reviewed 21 July 2019
    Beautiful home, great location, close to the action but off the main path. Family friendly vibes. Lagoon Pond and beach are within walking/riding distance. Family enjoyed the...
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    Island Sanctuary Book this dog-friendly home, complete with laundry, a grill, and a great location, for your next Martha's Vineyard vacation. Situated on a grassy plot in charming Oak Bluffs, this home puts you in the perfect location to walk to the gentle waters of Lagoon Pond or Sail Camp...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Island Inn - 40G A memorable vacation awaits you on Martha's Vineyard, and this two-level townhouse is the perfect place to stay! You'll have everything you could hope for with a shared pool, tennis courts, and the beach all within easy reach. Please be aware this rental has a unique layout, with...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Vineyard Haven This charming home on Martha's Vineyard is the perfect destination for your next family getaway. You'll enjoy a huge backyard with a private hedge, a picnic table, and a grill for summer cookouts, along with a private porch and terrace. Inside, you'll find two living rooms with...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Island Inn - 12D 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...
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    Oak Bluffs, Martha's Vineyard 02568
    Condo/Apartment - 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Island Inn - 8C 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'...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Island Inn - 36G Planning a Martha's Vineyard getaway with your friends and loved ones? You can't go wrong with this charming first-floor studio condo! Part of the Island Inn community, this cozy condo includes access to three shared tennis courts and a shared outdoor pool, not to mention all of...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
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    Island Inn - 6B 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...
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    Oak Bluffs, Martha's Vineyard 02568
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
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    Island Inn - 5B 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...
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    Oak Bluffs, Martha's Vineyard 02568
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Island Inn - 7C Fall in love with Martha's Vineyard during a stay in this lovely first-floor suite by the sea! You'll have access to the grounds' shared pool, BBQ area, and more. Plus, you're only a short drive or a leisurely half-mile walk away from the gorgeous shore. The family dog is also...
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    Oak Bluffs, Martha's Vineyard 02568
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Island Inn - 22F Show your special someone or your family 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...
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
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    Island Inn - 25F 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...
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    Oak Bluffs, Martha's Vineyard 02568
    Condo/Apartment - 1 Bathroom, Sleeps 4
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Vineyard Stride This new home, completed in August 2019, features over 2,800 square feet of bright, welcoming living space with an open floor plan and nine-foot ceilings. Prepare home-cooked meals in the gourmet kitchen, complete with high-end appliances, or fire up the new gas grill outside on the...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
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    Island Inn - 3B 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...
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Island Inn - 29G Discover Martha's Vineyard from this charming first-floor condo suite in the Island Inn community. With free WiFi, a well-equipped kitchen, shared swimming pool access, tennis courts, and a picnic and BBQ area, up to six guests are sure to have an unforgettable time at this rental....
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
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    Island Inn - 39G A family-friendly Martha's Vineyard getaway is within reach thanks to this charming one-bedroom vacation rental! Standard home conveniences and exceptional on-site amenities, including a shared pool and tennis courts, ensure that this comfy condo will be a dream come true for your...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Vineyard Walk This newly built home hosts a variety of comforts that can be hard to find on the historic island of Martha's Vineyard. This dog-friendly space comes equipped with central AC and two master bedrooms, allowing you unmatched comfort. The beautiful backyard lets you unwind and relax in...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Island Inn - 19D 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...
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    Oak Bluffs, Martha's Vineyard 02568
    Condo/Apartment - 1 Bathroom, Sleeps 4
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Vineyard Stroll This home was constructed in 2015, so it is equipped with all the modern accessories including central air! A full kitchen with newly purchased stainless steel appliances and an open concept layout makes this the perfect location to host a small gathering of friends for a week....
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Island Inn - 14D Fill your next vacation with stress-melting amenities, picturesque grounds, and hassle-free adventures when you book your trip to this Martha's Vineyard studio. Featuring access to the pristine pool, community tennis courts, and of course the postcard-perfect beaches, stress won't...
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    Oak Bluffs, Martha's Vineyard 02568
    Condo/Apartment - 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Island Inn - 15D Escape the daily grind and fill your days with stress-melting relaxation when you book your next vacation to this newly renovated Martha's Vineyard condo. Guests will have access to shared tennis courts, a pristine pool, and a location that puts you just a short walk from the...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Island Breeze Explore all that Martha's Vineyard has to offer at this centrally located, recently renovated home in a peaceful neighborhood of Oak Bluffs! This dog-friendly escape features everything you'll need for a fantastic getaway, including a well-appointed kitchen that opens to the living...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Island Inn - 33G Get ready to enjoy the best of Martha's Vineyard with a stay at this wonderful first-floor suite at the Island Inn! Located just half a mile from the beach, a stay at this rental also includes access to three tennis courts (with on-site professional lessons) and a shared outdoor...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Island Inn - 26F Make the most of Martha's Vineyard at this cozy first-floor studio with a well-equipped kitchenette located within the charming Island Inn Community. Guests of this rental will enjoy access to a number of resort amenities including a shared, outdoor pool, tennis courts, a business...
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    Oak Bluffs, Martha's Vineyard 02568
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Island Inn - 11D Explore all Martha's Vineyard has to offer from the comfort of this lovely first-floor studio! From the shared pool to the shared tennis court, this property has so much to offer its guests. Plus, the excellent location near the ocean can't be beat! Tee off at the gorgeous Farm...
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    Oak Bluffs, Martha's Vineyard 02568
    Condo/Apartment - 1 Bathroom, Sleeps 4
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Island Inn - 38G With access to resort amenities including a shared pool and tennis courts, this lovely first-floor condo is your ticket to a quintessential Martha's Vineyard vacation. You and your loved ones can relax in comfort and convenience at this one bedroom vacation rental, which is perfect...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Island Inn - 2A If you're headed to Martha's Vineyard and are looking for a family-friendly accommodation, make this comfortable and convenient two-bedroom condo your home base and enjoy a shared pool and tennis courts, as well as the perfect location for easy access to in-town conveniences and...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Island Inn - 45G Do beach waves and golfing on beautiful Martha's Vineyard sound like a great vacation to you? Look no further than this charming two-level townhouse with access to a shared pool, tennis courts, and proximity to the beach and neighboring golf course! Located on the scenic grounds...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Island Inn - 31G Coastal charm awaits in abundance at this lovely Martha's Vineyard condo! Located just half a mile from the glistening Atlantic Ocean, this island rental also includes a shared swimming pool, on-site tennis courts, plus modern conveniences like a flatscreen TV and free WiFi....
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Island Inn - 42G 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...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Island Inn - 18D Treat your special someone to a stress-free getaway at this Martha's Vineyard seaside condo. Guests will enjoy the shared pristine pool, on-site tennis courts, and easy beach access, making this is the perfect spot to revel in the surrounding beauty. The family dog is also welcome...
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    Oak Bluffs, Martha's Vineyard 02568
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Heated Pool, Hottub,AC,WiFi,sleep22, 2 mi to beach1 / 49
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    5 Bedrooms, 4 Bathrooms, Sleeps 22 Quick View
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    • Hot Tub
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    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...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 22
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