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 137 properties available
BR1 King en suite with tub/shower, 2nd floorBR2 Queen, 1st floorBR3 (2)Twin beds, 1st floorHall bath with shower, 1st floor
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Oak Bluffs 839
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Oak Bluffs
$2,800.00 - $7,000.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Rating 5 (1)
Oak Bluffs 839
Three bedroom, two bath home in Sengekontacket Association Community offers two tennis courts, a clubhouse on a spring fed freshwater pond and a saltw... Read More
June 2025
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1 2 3 4 5 6 $2800 7
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BR1 King with Laundry, Hall Bath. Pair of Queen Beds in Loft Over Living Room
Oak Bluffs 874
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Oak Bluffs
$1,800.00 - $3,750.00 / per week
Beds 1 beds
Baths 1 Full Bath
Sleeps 4 sleeps
Rating 5 (1)
Oak Bluffs 874
A stunning, newly renovated condo on Ocean Park - pristine finishes and a modern floorplan with an open concept kitchen, dining, and living area, stai... Read More
June 2025
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17 18 19 20 21 22 $3750 23
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BR1 (2)Twin beds, 1st floorHall bath with tub/shower, 1st floorBR2 King en suite with tub/shower, 1st floor
Oak Bluffs 8075
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Oak Bluffs
$2,800.00 - $5,000.00 / per week
Beds 2 beds
Baths 2 Full Bath
Sleeps 4 sleeps
Oak Bluffs 8075
Two bedroom, two bath beachfront condominium in Oak Bluffs. Beautiful views of Nantucket Sound. Close by to shops, restaurants and theaters. Just mome... Read More
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BR1 Queen, Second FloorBR2 Queen, Second FloorBR3 (5) Twin Beds, Second FloorHall Bath with Shower Tub Combo, Second FloorHall Bath with Shower Stall, First Floor
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Oak Bluffs 8065
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Oak Bluffs
$7,500.00 - $10,500.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 9 sleeps
Oak Bluffs 8065
By the sea, by the sea! Picture yourself on the deck of this wonderful East Chop home with private beach, sweeping views of Vineyard Sound, huge flat ... Read More
June 2025
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1 2 3 4 5 6 $7500 7
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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
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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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1 2 3 4 5 6 $12800 7
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BR1 Queen En Suite with Separate Shower Stall & Tub, First FloorBR2 Queen, Second FloorHall Bath with Tub Shower Combo, Second FloorBR3 Queen, Second FloorBR4 (2) Twin Beds & Bunk Bed, Second FloorHall Bath with Shower Stall, Second FloorBR5 (2) Bunk Beds & Trundle, Second FloorHall Bath with Shower Stall, First FloorLaundry Room, First Floor
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Oak Bluffs 8091
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Oak Bluffs
$4,900.00 - $18,000.00 / per week
Beds 5 beds
Baths 4 Full Bath
Sleeps 15 sleeps
Oak Bluffs 8091
Two Week Minimum. Enjoy a relaxing stay in a charming, secluded, five-bedroom, eco-friendly home that sleeps up to 15, complete with total privacy, s... Read More
June 2025
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1 2 3 4 5 6 $4900 7
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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
Oak Bluffs 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 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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BR1 Queen en suite with showerPlease note: No laundry on premise
Oak Bluffs 8156
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Oak Bluffs
$2,500.00 - $3,500.00 / per week
Beds 1 beds
Baths 1 Full Bath
Sleeps 2 sleeps
Oak Bluffs 8156
Guest cottage separate from main house with ocean view. Depart out the rear entrance and cross the street to Oak Bluffs town beach. Or, go out the f... Read More
June 2025
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1 2 3 4 5 6 $2500 7
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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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    1 2 3 4 $18825 5
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24 25 26 27 28 29 $18825 30
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BR1 Queen En Suite with Shower Stall, First FloorBR2 Queen En Suite with Tub, Second FloorBR3 Queen, Second FloorBR4 King & Twin Bed, Second FloorBR5 (2) Queen Beds, Second FloorBR6 (3) Twin Beds, Second FloorHall Bath with Separate Tub/Shower, Second Floor Powder Room/ Laundry, First Floor
Oak Bluffs 8014
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Oak Bluffs
$8,000.00 - $13,000.00 / per week
Beds 6 beds
Baths 3 Full, 1 Half Bath
Sleeps 14 sleeps
Oak Bluffs 8014
This six bedroom Oak Bluffs Gingerbread home is well appointed with a grand open floor plan, chefs kitchen, formal dining, front living space, spillin... Read More
June 2025
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1 2 3 4 5 6 $8000 7
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Main house:BR1 Queen Bedroom with AC split, First FloorBR2 Bunk Room Queen on the bottom, Twin on the top, AC split, First FloorBedrooms 1 and 2 share a Hall BathroomBR3 Queen Bedroom with a water view, Second FloorBR4 Queen Bedroom with a water view, Second FloorBR5 Queen Bedroom Second FloorBedrooms 3-5 share a Hall BathroomBR6 King Bedroom en-su
Oak Bluffs 8148
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Oak Bluffs
$15,000.00 - $38,000.00 / per week
Beds 9 beds
Baths 9 Full, 1 Half Bath
Sleeps 18 sleeps
Oak Bluffs 8148
This stunning property in Oak Bluffs has been completely renovated and features nine bedrooms. The Main House consists of six bedrooms, with two separ... Read More
June 2025
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22 23 24 25 26 27 $32000 28
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BR1 King en suite with tub and shower, 1st floorBR2 Queen with hall bath, 1st floorBR3 (2) Twins, (1) set of Twin bunks with hall bath, 1st floor
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Oak Bluffs 8032
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Oak Bluffs Pet Friendly
$7,000.00 - $12,000.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 8 sleeps
Rating 5 (1)
Oak Bluffs 8032
Dramatic views! Enjoy the perfect vacation spot for all families. Located on the lagoon side of Barnes road, this 3 bedroom home includes a small beac... Read More
June 2025
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1 2 3 4 5 6 $7000 7
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