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Oak Bluffs Pet Friendly Rentals

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    Travelers to Oak Bluffs are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    27 Matching Rentals in Oak BluffsView all 228 rentals
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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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    Heated Pool, Hottub,AC,WiFi,sleep22, 2 mi to beach1 / 49
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 22 Quick View
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    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
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    • Patio
    • Grill
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    • Waterfront
    • Porch
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 Park for your family...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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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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    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Spend the summer in one of New England's most desirable beach towns when you escape to this dog-friendly Oak Bluffs townhouse. You'll enjoy a private deck, shared resort amenities that include an outdoor pool and tennis courts, and walking access to beautiful ocean beaches. Please be aware this...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 Neck Golf Club,...
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 of The Island Inn,...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    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 beach. This is the...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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. The family dog...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 for a small...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 6
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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
    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
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 center, a...
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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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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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), a shared outdoor pool, and a playground...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 stand a chance...
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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
    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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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 year-round outdoor...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    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 group. The family...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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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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    • Cable/satellite TV
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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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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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, kids' playground, 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 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    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 to join you here...
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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 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, and a playground for the kids, plus modern conveniences like a flatscreen TV and...
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    Oak Bluffs, Martha's Vineyard 02557
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 6
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