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Cheap Oak Bluffs Holiday Homes

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    Travellers to Oak Bluffs are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    57 Matching Rentals in Oak BluffsView all 230 rentals
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    About this property
    Perfect for couples or close friends, this first-floor Island Inn condo has everything you need for a fantastic trip to Martha's Vineyard! Enjoy on-site perks like a shared pool and tennis courts, or venture out to experience New England's beaches, shops, and restaurants. You will enjoy a...
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    This studio-style condo is an excellent choice for travelers wanting to enjoy outdoor activities and a conveniently located home base while in Martha's Vineyard. You'll have amenities like a shared pool and tennis, as well as easy access to beaches, golf, and parks. This condo is located in the...
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    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
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    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
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    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
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    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
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    Whether you're looking for a romantic getaway or a relaxing New England retreat with a close friend, you'll love this walk-up 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...
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    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
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    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
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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
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    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
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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
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    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
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    About this property
    Book your trip to this seaside Martha's Vineyard retreat for a trip you'll never forget! With room for guests to enjoy the on-site tennis, shared pool, and easy beach access, you may never want to leave! Nestled on the beautiful grounds of the Island Inn on Martha's Vineyard, this second-floor...
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    Oak Bluffs, Martha's Vineyard 02557
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    About this property
    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
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    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
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    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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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    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
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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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    • 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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    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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Reserve your spot at this charming condo to experience the best of Martha's Vineyard! Spend as much time as you'd like at the property's shared pool, grilling area, and tennis courts. Plus, the beach is right around the corner. Golfers will be delighted to find the gorgeous Farm Neck Golf Club...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Clyde's Nook has the perfect atmosphere for families, with a bright, welcoming open-concept layout, a big backyard, fireplace, and modern amenities like free WiFi and a cable TV for entertainment. What's nearby: This cul-de-sac cottage is less than a mile from downtown Oak Bluffs, and nearby...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    You'll be within walking distance of gorgeous beaches and the heart of downtown Oak Bluffs at this three-bedroom Martha's Vineyard home, a light-filled escape with a private deck, a beautifully appointed interior, and a convenient in-town location with a tranquil out-of-town feel. Tucked away on...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    This sweet, little (it's priced accordingly!)cottage is all about convenience. It is within walking distance to the center of Oak Bluffs and two town beaches. The interior of the cottage has recently been redone inside and is fresh & clean and perfect for a great vacation. Large decks, lovely...
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    Oak Bluffs, Martha's Vineyard 02539
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Lovely Oak Bluffs home one mile from town and beach1 / 23
    (1)Very good
    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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    COME EXPERIENCE THE MAGIC OF THE VINEYARD1 / 14
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Come experience the magic of the Vineyard in our island home. Modernized in 2011, this charming residence is clean, cozy and boasts new furniture and decor. Amenities include 3 TV’s, cable television, Wi-fi, DVD, telephone, I-home, and Keurig Coffee maker. The property has a private yard, sundeck,...
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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 7 Quick View
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    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    In-Town Historic Property on Martha's Vineyard1 / 20
    (67)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Reviewed 2 July 2018
    Firstly, we were travelling from the U.K. In our view, the apartment needs attention internally and we were disturbed until the early hours by a resident and staff of the nearby...
    Reviewed 12 June 2018
    I enjoyed the entire trip to no end. The stay was excellent the location perfect. You are in a great town Oak Bluffs you’re with in walking distance to everything you could...
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    About this property
    This Oak Bluffs, Martha's Vineyard rental is a certified National Historic Property. Ideal location for visitors in the middle of the most active, multi-cultural, charming, and fun town on Martha's Vineyard. Step outside your door for breakfast or ice cream, a great selection of restaurants in...
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Ready for an unforgettable vacation to Martha's Vineyard? Choose this cute two-bedroom condo and enjoy a shared pool and tennis courts, as well as close proximity to golf and beaches! You'll be situated within the Island Inn community at the edge of the Farm Neck Golf Club. Joseph Sylvia State...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Tucked away among the shade trees on Martha's Vineyard, this delightful cabin in the woods is ideal for your next family vacation or getaway with a few close friends. This three-bedroom rental is located less than a mile from the top-ranked, semi-private Farm Neck Golf Club as well as the Trade...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Charming house with lots of entertainment and gourmet kitchen!1 / 24
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 2 weeks ago
    The house was clean and centrally located. It was decorated with updated decor. The setting was quiet. It was perfect for our family.
    Reviewed 11 October 2017
    Everyone who stayed here loved the place. We were down for a wedding and pretty much just wanted to chill before the wedding on Saturday and the place had everything, great...
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    About this property
    You'll love this Oak Bluffs vacation rental with plenty of entertainment and a beautiful gourmet kitchen! The surrounding area is quiet and residential, and the water is less than a mile to the northwest. To get to the heart of Oak Bluffs and its shops and restaurants, it's just a mile to the...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Immerse yourself in the charms of Oak Bluffs at this Martha's Vineyard home, a wonderfully walkable escape with a private patio, a tree-lined yard, and outstanding access to beaches, restaurants, and the ferry terminal. Conveniently situated a few blocks west of downtown Oak Bluffs, this newly...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    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 the usual home...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Pet friendly
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    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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    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
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Pet friendly
    Kid friendly
    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
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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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
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Smoking allowed
    About this property
    Comfort meets convenience at this lovely Martha's Vineyard vacation rental, which features a shared outdoor pool, on-site tennis courts, and all of the home amenities your group could wish for. In addition, the beach is mere minutes away, making this vacation rental perfect for a family-friendly...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Choose the ocean breezes and sunny skies of Martha's Vineyard for your next New England getaway, and book your stay at this charming first-floor condo suite at the Island Inn! Boasting an incredible array of amenities, including on-site tennis, a shared outdoor pool, and a great location less than...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A family-friendly Martha's Vineyard getaway is within reach when you book this first-floor condo suite, which has one bedroom, a separate sleeping area, and room for up to six guests. Featuring on-site amenities including tennis courts, a shared pool, and a barbecue area, in addition to home...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 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
    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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    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 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
    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
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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