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Oak Bluffs Holiday Rentals

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Holiday Rentals (53)

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Featured listings
1225
1225
    Price: £668 - £1,882/week
  • Bedrooms: 3, sleeps 6
  • Bathrooms: 3
  • Min stay: 1
    • Contact Manager
1142
1142
    Price: £850 - £1,336/week
  • Bedrooms: 3, sleeps 5
  • Bathrooms: 1
    • Contact Manager
1449
1449
    Price: £789 - £1,518/week
  • Bedrooms: 4, sleeps 8
  • Bathrooms: 2
    • Contact Manager
878
878
    Price: £1,093 - £2,368/week
  • Bedrooms: 4, sleeps 8
  • Bathrooms: 3
    • Contact Manager
619
619
    Price: £2,125 - £4,553/week
  • Bedrooms: 5, sleeps 10
  • Bathrooms: 3
    • Contact Manager
1490
1490
    Price: £1,761 - £3,157/week
  • Bedrooms: 7, sleeps 14
  • Bathrooms: 3
    • Contact Manager
1334
1334
    Price: £4,250 - £5,768/week
  • Bedrooms: 7, sleeps 14
  • Bathrooms: 7
    • Contact Manager
1290
1290
    Price: £1,214 - £2,064/week
  • Bedrooms: 4, sleeps 8
  • Bathrooms: 3
    • Contact Manager
1172
1172
    Price: £607 - £1,184/week
  • Bedrooms: 3, sleeps 6
  • Bathrooms: 1
    • Contact Manager
1345
1345
    Price: £2,428 - £4,705/week
  • Bedrooms: 7, sleeps 14
  • Bathrooms: 4
    • Contact Manager

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1489
1489
Contact Manager
4.5 of 5 stars 3 reviews
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 6
Bathrooms: 4
Policy: Pets not allowed, Not handicap accessible
  • Nightly
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  • Weekly
    £1,518 - £1,821
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845
845
Contact Manager
4 of 5 stars 1 review
Management: Professional
Property: Holiday Rental House
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
    £850 - £1,821
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474
474
Contact Manager
4 of 5 stars 1 review
Management: Professional
Property: Holiday Rental House
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 ...
  • Nightly
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  • Weekly
    £729 - £1,093
  • Monthly
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1179
1179
Contact Manager
4 of 5 stars 1 review
Management: Professional
Property: Holiday Rental House
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 ...
  • Nightly
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  • Weekly
    £1,032 - £1,275
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1123
1123
Contact Manager
4 of 5 stars 1 review
Management: Professional
Property: Holiday Rental House
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
    £2,307 - £2,853
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1325
1325
Contact Manager
4 of 5 stars 2 reviews
Management: Professional
Property: Holiday Rental House
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
    £1,214 - £1,457
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803
803
Contact Manager
4 of 5 stars 2 reviews
Management: Professional
Property: Holiday Rental House
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
    £2,125 - £3,218
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1189
1189
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 7
Bathrooms: 4
Main and Guest House Policy: Pets not allowed, Not handicap accessible
  • Nightly
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  • Weekly
    £1,518 - £2,368
  • Monthly
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1085
1085
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 8
Bathrooms: 3
This charming home sits atop the Lagoon bluffs w/stairs down to a narrow private beach It offers waterviews from many rooms (including a wonderful glassed ...
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  • Weekly
    £1,518 - £2,550
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651
651
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 8
Bathrooms: 2
Min stay:1
Set back well off the road, this elegant Island home and it's surrounding open grounds are in a perfect mid-Island location for easy access to towns and ...
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  • Weekly
    £729 - £2,034
  • Monthly
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809
809
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 8
Bathrooms: 3
Min stay:1
Wonderful, spacious, lovingly maintained and attractive home in exclusive setting - family room with fireplace, large formal living room with fireplace, ...
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  • Weekly
    £607 - £2,064
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499
499
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 8
Bathrooms: 3
LIGHT FILLED, COMFORTABLY FURNISHED, WELL MAINTAINED W/VIEWS ACROSS SALT POND TO NANTUCKET SOUND. TAKE LOVELY WALKS AROUND POND AND ALONG ROADS IN LANDSCAPED ...
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  • Weekly
    £850 - £1,578
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1533
1533
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 8
Bathrooms: 4
New Arts and Crafts style house, architect-designed, with lovely furnishings and spectacular views over Vineyard Sound from every room(except bathrooms)! Sit ...
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  • Weekly
    £3,461
  • Monthly
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1511
1511
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 5, sleeps 10
Bathrooms: 4
Our 'treehouse' is the tallest residence in the town of Oak Bluffs. Enjoy quiet and seclusion in this wooded setting, located in the exclusive Meadow View ...
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  • Weekly
    £971 - £2,368
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1354
1354
Contact Manager
Management: Professional
Property: Holiday Rental House
Bedrooms: 2, sleeps 6
Bathrooms: 2
A new Cape style residence situated on a wooded lot near bike path and just a short ride to town center and ferry. This home features an open design with a ...
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  • Weekly
    £607 - £1,093
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Oak Bluffs Holiday Rental Advice
SURFING in Martha's Vineyard??
Posted by jdross, 24 Jul 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, 25 Jul 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, 4 May 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, 8 May 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, 19 Mar 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, 20 Mar 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, 25 Aug 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