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 141 properties available
BR1 Queen en suite with shower stall, 1st floorBR2 Queen and twin bed, 2nd floorBR3 Queen, 2nd floorHall bath with tub/shower, 2nd floorLaundry facilities, 1st floorHalf bath, 1st floor
Oak Bluffs 816
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Oak Bluffs
$8,000.00 - $8,500.00 / per week
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps 6 sleeps
Oak Bluffs 816
Lovely and very well maintained three bedroom two and a half bathroom, custom home is located in the quiet neighborhood of Meadowview Farms. This home... Read More
June 2025
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BR1 Queen, 1st floorBR2 (2)Twin beds, 1st floorBR3 Queen, 1st floorHall bath with tub/shower, 1st floorLaundry facilities, 1st floorHalf bath, 2nd floor all bedrooms are located on the lower level.
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Oak Bluffs 8011
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Oak Bluffs
$3,500.00 - $4,000.00 / per week
Beds 3 beds
Baths 1 Full, 1 Half Bath
Sleeps 6 sleeps
Rating 5 (2)
Oak Bluffs 8011
Sparkling Vineyard reverse level cottage has the fresh airy updates with painted white shiplap for wall decor, hardwoods and stainless steel to comple... Read More
June 2025
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BR 2 - Queen>Loft - King and two twins>Shared bath on main level
Oak Bluffs 847
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Oak Bluffs
$3,100.00 - $5,885.00 / per week
Beds 2 beds
Baths 1 Full Bath
Sleeps 8 sleeps
Oak Bluffs 847
Welcome to this charming rental on Martha's Vineyard on Circuit Avenue in Oak Bluffs. This delightful apartment offers comfortable and spacious accomm... Read More
June 2025
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BR1 King, Second FloorBR2 Queen, First FloorBR3 Bunk Bed and a Double, Second Floor Hall Bath with Shower Stall, First FloorHall Bath with Tub/Shower, Second Floor
Oak Bluffs 830
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Oak Bluffs Pet Friendly
$3,500.00 - $6,200.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 7 sleeps
Oak Bluffs 830
This rental home is a true gem, nestled in a peaceful, natural setting on a private, dead-end road. The exterior of the home features a large back dec... Read More
June 2025
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1 2 3 4 5 6 $4440 7
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BR1 Queen, 1st floorHall bath with tub/shower, 1st floorBR2 (2)Twin beds, 2nd floorBR3 Queen, 2nd floorHall bath with tub/shower, 2nd floorBR4 Queen, 2nd floor loftHall bath with tub/shower, 2nd floor loft
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Oak Bluffs 8170
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Oak Bluffs
$11,800.00 - $16,000.00 / per week
Beds 4 beds
Baths 3 Full Bath
Sleeps 10 sleeps
Oak Bluffs 8170
Easy breezy summer living in this fresh and beautifully renovated, airy cape. Designed with a relaxed modern vibe, this house forces you to have a rel... Read More
June 2025
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BR1 King en suite with shower stall, 1st floorBR2 King en suite with shower stall, 1st floorBR3 (2)Twin beds en suite tub/shower, 1st floorBR4 King en suite with shower stall, 1st floorBR5 (2)Twin beds, 1st floorHall bath with tub/shower, 1st floorBR6 King en suite with shower stall, 1st floorLaundry facilities, 1st floorHalf bath, 1st floor
Oak Bluffs 809
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Oak Bluffs
$10,300.00 - $18,500.00 / per week
Beds 6 beds
Baths 6 Full, 1 Half Bath
Sleeps 12 sleeps
Oak Bluffs 809
2 week minimum. Prime waterfront Oak Bluffs property in the serene Farm Neck Golf course neighborhood you will find a six bedroom, six and a half bath... Read More
June 2025
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BR1 King En Suite with Tub & Shower, Second FloorBR2 Queen, Second FloorBR3 Queen, Second FloorHall Bath with Shower/Tub, Second FloorBR4 (2) Twins, Second FloorAdditional Sleeping Double, Lower LevelHall Bath with Tub Shower Combo, Lower LevelBR5 King En Suite with Tub Shower Combo, Guest HousePowder Room, First Floor
Oak Bluffs 812
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Oak Bluffs Pet Friendly
$14,000.00 - $21,000.00 / per week
Beds 5 beds
Baths 4 Full, 1 Half Bath
Sleeps 12 sleeps
Rating 5 (1)
Oak Bluffs 812
Enjoy this sprawling property packed with activities for all, and fantastic views of the ocean. This home includes a spacious main house, guest house,... Read More
June 2025
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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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BR1 Queen En Suite with Shower Stall, First FloorBR2 Queen En Suite with Shower Stall, Second FloorBR3 Queen, Second FloorHall Bath with Shower Tub Combo, Second FloorBR4 (2) Twin Beds, Second FloorHall Bath with Tub and Handheld Shower, First FloorPowder Room, Lower LevelGuest House:BR5 Queen En Suite with Shower Tub Combo, First Floor
Hot HOT 27
Oak Bluffs Main and Guest House 8172
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Oak Bluffs
$4,300.00 - $7,300.00 / per week
Beds 5 beds
Baths 5 Full, 1 Half Bath
Sleeps 10 sleeps
Rating 5 (1)
Oak Bluffs Main and Guest House 8172
Beautifully appointed custom five bedroom gingerbread main and guest house in the heart of Oak Bluffs awaits your summer vacation. It has been updated... Read More
June 2025
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8 9 10 11 12 13 $5300 14
15 16 17 18 19 20 $7300 21
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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 Queen en suite with separate tub and shower, 2nd floorBR2 Queen en suite with shower, 3rd floor loftBR3 Double, 1st floorBR4 (2)Twin beds, 1st floorHall bath with tub/shower, 1st floorHalf bath, 1st floor
Oak Bluffs 8174
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Oak Bluffs
$5,000.00 - $10,000.00 / per week
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps 8 sleeps
Rating 5 (1)
Oak Bluffs 8174
Lovely Oak Bluffs home located in Sengekontacket. This home offers great space and multiple amenities to enjoy your summer get away. Association ten... Read More
June 2025
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15 16 17 18 19 20 $7500 21
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BR1 Queen en suite with shower stall, 1st floorBR2 Queen, 1st floorHall bath with shower stall, 1st floorBR3 (2)Double beds en suite with shower stall, 2nd floorBR4 Queen, 2nd floorHall bath with shower stall, 2nd floorBR5 King en suite with shower stall, 2nd floor
Oak Bluffs 8814
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Oak Bluffs
$18,825.00 / per week
Beds 5 beds
Baths 5 Full Bath
Sleeps 10 sleeps
Oak Bluffs 8814
A stunning five bedroom bungalow overlooking Nantucket Sound, with an expansive porch offering one of the greatest views on the Island. Inside, the ho... Read More
June 2025
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15 16 17 18 19 20 $18825 21
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