Oak Bluffs

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Oak Bluffs - or 'OB' - is a classic beach town, filled with tons of fun! Enjoy the sandy beaches along the calm waters of Nantucket Sound, events held in Ocean Park and the Tabernacle, and the casual atmosphere of the harbor and Circuit Avenue. Popular attractions include the Flying Horses Carousel, the nation’s oldest operating platform carousel, and the Martha’s Vineyard Camp Meeting Association, a National Historic Landmark and community of over 300 charming Victorian gingerbread cottages surrounding a beautiful iron Tabernacle. Circuit Avenue is always bustling and has something for everyone – ice cream, coffee shops, eateries, bars and boutiques. The Harbor is entirely walkable and is a great place to relax and watch the boats coming and going. Outside of the downtown area, there are many areas in OB that offer a quieter atmosphere. Contact us and we'll help you find the perfect getaway!


Properties Available 142 properties available
br>Guest apartment: BR5 Queen, 2nd floorHall bath with tub/shower, 2nd floorHalf bath, 1st floorHall bath with shower stall, lower level
Oak Bluffs 8106
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Oak Bluffs
$7,000.00 - $16,500.00 / per week
Beds 5 beds
Baths 5 Full, 1 Half Bath
Sleeps 10 sleeps
Oak Bluffs 8106
The Weku House is a luxurious, 5,000 square foot home located in the beautiful town of Oak Bluffs on Martha's Vineyard. Elegantly decorated with desi... Read More
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BR 1 Queen, 2nd floor BR 2 Queen, 2nd floor BR 3 Two Twins, loft/3rd floor All bedrooms share hall bath with shower, 1st and 2nd floor
Hot HOT 14
Oak Bluffs Condo 8015
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Oak Bluffs
$4,000.00 - $5,000.00 / per week
Beds 2 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Rating 5 (1)
Oak Bluffs Condo 8015
Sengekontacket Association offers a charming residential community with convenient access to tennis courts and a picturesque pond, all just a short di... Read More
June 2025
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1 2 3 4 5 6 $4000 7
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BR1 King en suite shower stall, 2nd floorBR2 Queen, 1st floorBR3 Queen,1st floorBR4 Daybed, 2nd floorGuest house: BR5 (2)Twin beds en suite with shower stall, 1st floorhall bath first floor
Oak Bluffs 8154
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Oak Bluffs
$12,000.00 - $21,000.00 / per week
Beds 5 beds
Baths 3 Full Bath
Sleeps 9 sleeps
Oak Bluffs 8154
Enjoy high end living, with commanding water views and Vineyard Haven beyond while living in this luxurious and meticulously detailed home with guest ... Read More
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10 11 12 13 14 15 $21000 16
17 18 19 20 21 22 $17000 23
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BR1 Double, First FloorBR2 Double Sofa Bed with Split Mattress, First FloorHall bath with Shower, First FloorLaundry, First Floor
Oak Bluffs 8044
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Oak Bluffs
$2,800.00 / per week
Beds 2 beds
Baths 1 Full Bath
Sleeps 4 sleeps
Oak Bluffs 8044
Newly constructed guesthouse with all the amenities of a Vineyard vacation home. Two bedrooms with shared hall bathroom. Fully equipped eat-in kitch... Read More
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BR1 Queen en suite with tub/shower combo, 2nd floorAdditional Sleeping, Queen, 2nd Floor Open LoftAdditional Room (2) Twins, 1st floorHall baths with tub/shower combo on 1st and 2nd floors
Oak Bluffs 832
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Oak Bluffs
$3,000.00 - $5,000.00 / per week
Beds 1 beds
Baths 3 Full Bath
Sleeps 6 sleeps
Oak Bluffs 832
Centrally located, custom colonial, in Oak Bluffs. Cook a true Vineyard feast from the wonderfully designed chef's kitchen with Wolf Gas stove. The k... Read More
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BR1 King En suite with Soaking Tub and Shower, First FloorBR2 Queen En suite with Shower Stall, First FloorBR3 Queen En suite with Shower Stall, First FloorBR4 Queen En suite with Shower Stall, First Floor
Oak Bluffs 8134
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Oak Bluffs
$23,000.00 - $24,000.00 / per week
Beds 4 beds
Baths 5 Full, 1 Half Bath
Sleeps 8 sleeps
Oak Bluffs 8134
A stunning four-bedroom home in one of the prestigious "Preserve" neighborhood in Oak Bluffs - perched on a hill overlooking the pond, the sprawling ... Read More
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BR1 King En Suite with Shower Stall, Second FloorBR2 Queen, Lower LevelBR3 (2) Twin Beds En Suite with Shower Stall, Second FloorAdditional Sleeping Queen Sofa Bed in Den En Suite with Shower, First FloorFull Bath, Lower LevelHalf Bath, First Floor
Oak Bluffs 8013
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Oak Bluffs
$4,500.00 - $8,000.00 / per week
Beds 3 beds
Baths 4 Full, 1 Half Bath
Sleeps 7 sleeps
Rating 5 (1)
Oak Bluffs 8013
Attractive Hidden Cove home. Large open living and dining room, stylishly appointed & recessed on 1.5 wooded acres, this multi-level home allows guest... Read More
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BR1 Queen, en suite, first floorBR2 Queen, en suite, second floorBR3 (2) Twins, hall bath, second floor
Oak Bluffs 804
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Oak Bluffs
$3,000.00 - $10,000.00 / per week
Beds 3 beds
Baths 3 Full, 1 Half Bath
Sleeps 6 sleeps
Oak Bluffs 804
Escape to your own piece of paradise on Martha's Vineyard in this recently renovated 3-bedroom, 3.5 bath vacation home! Nestled in a tranquil setting,... Read More
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BR1 Queen en suite with shower stall, 1st floorBR2 (2)Twin beds, 2nd floorBR3 Queen and twin, 2nd floorHall bath with tub/shower, 2nd floorLaundry facilities, 1st floorHalf bath, 1st floor
Hot HOT 12
Oak Bluffs 862
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Oak Bluffs
$3,000.00 - $5,000.00 / per week
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps 7 sleeps
Oak Bluffs 862
Three bedroom Colonial located in prestigious Meadow View Farms. Property offers granite countertops with stainless steel appliances, hardwood floors ... Read More
June 2025
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1 2 3 4 5 6 $3600 7
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BR1 King en suite, 1st floorBR2 Queen en suite, 2nd floorBR3 (2)Twin beds, 2nd floorHall bath of tub shower combo, 2nd floor
Oak Bluffs 814
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Oak Bluffs
$5,000.00 / per week
Beds 3 beds
Baths 3 Full, 1 Half Bath
Sleeps 8 sleeps
Rating 4 (1)
Oak Bluffs 814
Lovely Oak Bluffs home in a private location with association access to Sengekontacket Pond. Just a street over from Farm Neck Golf and Tennis. Minu... Read More
June 2025
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BR1 King En Suite with Shower Stall, Second FloorBR2 Queen, Second FloorHall Bath with Tub/Shower Combo, Second FloorBR3 (2) Double Beds, Second FloorPowder Room, First Floor
Oak Bluffs 8063
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Oak Bluffs
$3,500.00 - $6,500.00 / per week
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps 8 sleeps
Oak Bluffs 8063
Nestled in a quiet area of Oak Bluffs, yet convenient to all areas of the island, this inviting renovated colonial is the ideal spot for a peaceful is... Read More
June 2025
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1 2 3 4 5 6 $5600 7
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BR1 Queen, First FloorHall Bath with Shower Stall, First FloorBR2 (2) Twin Beds, Second FloorHall Bath with Tub Shower Combo, Second FloorBR3 (2) Twin Beds, Second Floor
Hot HOT 11
Oak Bluffs 8158
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Oak Bluffs
$3,500.00 - $5,000.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Oak Bluffs 8158
Your Vineyard Vacation awaits at this cozy 3 Bedroom, 2 Bath Cape Cod Style home located in the Lagoon Heights neighborhood of Oak Bluffs. The newly r... Read More
June 2025
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1 2 3 4 5 6 $4500 7
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