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Oak Bluffs Vacation Rentals

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Vacation Rentals (53)

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Featured listings
1238
1238
    Price: $3,500 - $5,500/week
  • Bedrooms: 6, sleeps 10
  • Bathrooms: 3
    • Contact Manager
1511
1511
    Price: $1,600 - $3,900/week
  • Bedrooms: 5, sleeps 10
  • Bathrooms: 4
    • Contact Manager
913
913
    Price: $1,500 - $2,300/week
  • Bedrooms: 3, sleeps 7
  • Bathrooms: 2
    • Contact Manager
1458
1458
    Price: $5,000 - $6,000/week
  • Bedrooms: 4, sleeps 8
  • Bathrooms: 3
    • Contact Manager
1354
1354
    Price: $1,000 - $1,800/week
  • Bedrooms: 2, sleeps 6
  • Bathrooms: 2
    • Contact Manager
1526
1526
    Price: $1,100 - $1,700/week
  • Bedrooms: 2, sleeps 5
  • Bathrooms: 1
    • Contact Manager
1225
1225
    Price: $1,100 - $3,100/week
  • Bedrooms: 3, sleeps 6
  • Bathrooms: 3
  • Min stay: 1
    • Contact Manager
1142
1142
    Price: $1,400 - $2,200/week
  • Bedrooms: 3, sleeps 5
  • Bathrooms: 1
    • Contact Manager
1503
1503
    Price: $1,500 - $4,000/week
  • Bedrooms: 4, sleeps 6
  • Bathrooms: 2
    • Contact Manager
1396
1396
    Price: $1,500 - $3,300/week
  • Bedrooms: 4, sleeps 8
  • Bathrooms: 4
    • Contact Manager

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1489
1489
Contact Manager
4.5 of 5 stars 3 reviews
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 4
Policy: Pets not allowed, Not handicap accessible
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  • Weekly
    $2,500 - $3,000
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474
474
Contact Manager
4 of 5 stars 1 review
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 2
IN A CENTRAL LOCATION (CLOSE TO A BIKE PATH) THIS SPACIOUS HOME IS SET ON A HALF ACRE LOT ON A DEAD END ROAD. THE LIVING AREA IS AN OPEN FLOOR PLAN W/A ...
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  • Weekly
    $1,200 - $1,800
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845
845
Contact Manager
4 of 5 stars 1 review
Management: Professional
Property: Rental Home
Bedrooms: 5, sleeps 10
Bathrooms: 2
Classic & charming, turn of the century "campground" home situated on a 4,400 sq. ft. corner lot just a few minutes walk from the beach & town. Spacious & ...
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  • Weekly
    $1,400 - $3,000
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803
803
Contact Manager
4 of 5 stars 2 reviews
Management: Professional
Property: Rental Home
Bedrooms: 8, sleeps 17
Bathrooms: 3
Min stay:1
Although carefully renovated and redecorated in 1996, this house retains its authentic charm yet serves the modern day vacationer well. The 8 bedrooms afford ...
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  • Weekly
    $3,500 - $5,300
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1179
1179
Contact Manager
4 of 5 stars 1 review
Management: Professional
Property: Rental Home
Bedrooms: 2, sleeps 4
Bathrooms: 1
Min stay:1
The quintessential Vineyard cottage!!! This sweet cottage brings back visions of the lazy days of summer of bygone eras when life was less hurried. The serene ...
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  • Weekly
    $1,700 - $2,100
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1123
1123
Contact Manager
4 of 5 stars 1 review
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 3
Min stay:1
NEWLY RENOVATED (including hardwood floors) AND EXPANDED IN 2008! Located in a secluded setting, this versatile home looks out over the trees to ...
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  • Weekly
    $3,800 - $4,700
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1325
1325
Contact Manager
4 of 5 stars 2 reviews
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 2
Sun filled and airy prow front contemporary home with beautiful views of Lagoon Pond. Four bedrooms accommodating up to eight guests. Two full baths plus ...
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  • Weekly
    $2,000 - $2,400
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1401
1401
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 8, sleeps 14
Bathrooms: 3
Twelve room Gothic Victorian located in the heart of Oak Bluffs where you are just steps to the beach, fine shops, restaurants and theater. There are ...
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  • Weekly
    $2,700 - $5,000
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1398
1398
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 6, sleeps 12
Bathrooms: 3
Watch the boats come and go from the harbour while you picnic and relax on your beach. This fabulous waterfront three bedroom main house and three bedroom ...
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  • Weekly
    $3,000 - $8,900
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1449
1449
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 2
Policy: Pets allowed, Not handicap accessible
  • Nightly
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  • Weekly
    $1,300 - $2,500
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1290
1290
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 3
This spacious condominium with its four bedroom and three full bathrooms has the advantage of an Association pool within a 2 minute walk and two tennis ...
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  • Weekly
    $2,000 - $3,400
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619
619
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 5, sleeps 10
Bathrooms: 3
Comfortable, spacious Victorian-style cottage overlooking conservation land and private association beach and harbor. Ocean views from the screened and open ...
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  • Weekly
    $3,500 - $7,500
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1334
1334
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 7, sleeps 14
Bathrooms: 7
Located on over 1 acre of direct oceanfront property on East Chop, an exclusive area of historic Oak Bluffs, this unique home is perfect for family and ...
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  • Weekly
    $7,000 - $9,500
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1490
1490
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 7, sleeps 14
Bathrooms: 3
Classic, "Camp Ground" over sized 7 bedroom 3 bath home in a residential neighborhood within easy walking distance to the beach, shops, restaurants, ...
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  • Weekly
    $2,900 - $5,200
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1172
1172
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 1
This adorable home is filled with Vineyard charm! Great location!! Convenient in-town Oak Bluffs location - Short walk to: beaches, ferry, harbor,shops, art ...
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  • Weekly
    $1,000 - $1,950
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Oak Bluffs Vacation Rental Advice
SURFING in Martha's Vineyard??
Posted by jdross, Jul 24, 2006
By any chance, is there actually any surf to ride in Martha's Vineyard? I picture it to be all cliffs, rocky and dangerous, but there are beaches mentioned. Any advice to a girl with a husband that only goes on vacation where there is surf?? ... more
Posted by Knows, Jul 25, 2006
... s a Trustees of Reservations property, so there are limited cars allowed and a small entrance fee, but it's open to the public. Some South beaches are better than others. Chilmark has two beaches good for surf; Lucy Vincent and Squibnocket. You'll need a pass, in the summer ... more
A question about beaches
Posted by digijules, May 4, 2009
I'm thinking about renting a condo on MV this summer and have read that it's difficult to get on private beaches in the summer. Are there public beaches to go to? If I'm renting a condo and want beach time, what are my options? ... more
Posted by Knows, May 8, 2009
What condos are you looking at? What town? There really aren't that many condos on the island, but maybe a few in Oak Bluffs, and a couple in both Edgartown and Vineyard Haven. ... more
Rent a House or Stay in a Condo?
Posted by NjJoeD, Mar 19, 2009
... action. If you prefer a condo, there's one that seems nice very close to South Beach. Can't recall the name, but you may find it on the web. Other than that complex, I don't believe there are too many condos in Edgartown/Katama area. Or elsewhere on ... more
Posted by Knows, Mar 20, 2009
... many for house rentals. Mattakeesett condos are the ones the previous poster is talking about. Seaview condos are in Oak Bluffs. You can also rent a house in Chilmark or West Tisbury with a beach pass to either Lucy Vincent beach or Squibnocket. These are both beautiful and on the ... more
Staying on the vineyard?
Posted by spankyCT, Aug 25, 2005
... your money...we had a condo, that slept 6 and it cost 265 per night. There was one bedroom with a queen size bed and half bath and then there was an area with two twin beds, a half wall seperates that with the living room area and in the ... more
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Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns