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
BR1 Queen en suite with tub/shower, 1st floorBR2 King en suite with separate tub with french shower and shower stall, 2nd floorBR3 King, 2nd floor,BR4 Queen, 2nd floorHall bath with tub and french showerHalf bath, 1st floor
Oak Bluffs 818
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Oak Bluffs
$13,500.00 / per week
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps 8 sleeps
Oak Bluffs 818
Classic East Chop Victorian with all of the amenities that they didn't have back then! While away a summer afternoon sitting on the porch watching the... Read More
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BR1 King En Suite with Shower Stall, First FloorBR2 Queen, First FloorHall Bath with Tub Shower Combo, First FloorBR3 (2) Twin Beds, First FloorPowder Room, First FloorOverflow: Queen over Queen & Twin XL over Twin XL Bunk Bed, Lower LevelHall Bath with Shower Stall, Lower Level
Oak Bluffs 840
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Oak Bluffs
$3,000.00 - $7,500.00 / per week
Beds 3 beds
Baths 3 Full, 1 Half Bath
Sleeps 8 sleeps
Oak Bluffs 840
This rental house is a contemporary and inviting home that combines modern amenities with a cozy Cape feel. The spacious and open concept living area ... Read More
June 2025
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17 18 19 20 21 22 $7500 23
24 25 26 27 28 29 $6300 30
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BR1 King En Suite with Tub Shower Combo, Second FloorBR2 Queen & Twin Bed, Second FloorBR3 King, Lower LevelHall Bath with Tub Shower Combo, Lower LevelBR4 Queen, Lower LevelPowder Room, First Floor
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Oak Bluffs 8024
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Oak Bluffs
$5,000.00 - $8,500.00 / per week
Beds 4 beds
Baths 2 Full, 1 Half Bath
Sleeps 9 sleeps
Oak Bluffs 8024
This newly renovated home located in Hidden Cove in Oak Bluffs sleeps 9 with 4 bedrooms and 2.5 bathrooms. The modern kitchen equipped with stainless ... Read More
June 2025
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BR1 Queen, First FloorBR2 (2) Double Beds En Suite with Shower Stall, Second FloorBR3 (2) Twin Beds, Second Floor Additional Sleeping Queen, Lower LevelHall Bath with Tub/Shower, First FloorHall Bath with Tub/Shower, Second Floor
Oak Bluffs 8012
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Oak Bluffs
$8,750.00 - $12,500.00 / per week
Beds 3 beds
Baths 3 Full Bath
Sleeps 8 sleeps
Oak Bluffs 8012
Set on a quiet cul de sac, yet one mile to the heart of Oak Bluffs. Step into this light filled, newly decorated home and let the vacation begin. With... Read More
June 2025
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1 2 3 4 5 6 $8750 7
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13 14 15 16 17 18 $10000 19
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BR1 King, 2nd floorBR2 Queen, 2nd floorHall bath with shower stall, 2nd floorHalf Bath and Laundry facilities, 1st floor
Hot HOT 12
Oak Bluffs 8077
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Oak Bluffs
$3,800.00 - $5,000.00 / per week
Beds 2 beds
Baths 1 Full, 1 Half Bath
Sleeps 4 sleeps
Rating 4.5 (2)
Oak Bluffs 8077
A classic Oak Bluffs Cottage has been renovated and revamped for 2023, adding air conditioning, a large sunroom and an additional half bath to this al... Read More
June 2025
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1 2 3 4 5 6 $3800 7
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BR1 King en suite with jacuzzi tub and shower, 1st floorBR2 King en suite with tub/shower, 2nd floorBR3 King en suite with tub/shower, 2nd floorBR4 (2)Queen beds en suite with tub/shower, lower level
Oak Bluffs 8107
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Oak Bluffs
$2,800.00 - $22,000.00 / per week
Beds 4 beds
Baths 7 Full Bath
Sleeps 10 sleeps
Oak Bluffs 8107
Stunning waterfront home on the Lagoon with a private pool. You feel like you are wondering into paradise when you enter the front door. Truly a Vin... Read More
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BR1 (2)Twin beds, 1st floorHall bath with tub/shower, 1st floorBR2 Queen, 2nd floorBR3 Queen, 2nd floorHall bath with tub/shower, 2nd floor
Oak Bluffs 8105
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Oak Bluffs
$4,200.00 - $7,400.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Rating 5 (2)
Oak Bluffs 8105
This wonderful three bedroom Cape is located in a quiet neighborhood in the development of Deer Run just off of Barnes Road in Oak Bluffs. There is so... Read More
June 2025
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1 2 3 4 5 6 $5600 7
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BR1 King en suite with tub/shower, 1st floorBR2 (2)Twin beds 1st floorHall bath with tub/shower, 1st floor
Oak Bluffs 8093
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Oak Bluffs
$2,800.00 - $4,900.00 / per week
Beds 2 beds
Baths 2 Full Bath
Sleeps 4 sleeps
Oak Bluffs 8093
Two bedroom beachfront condominium with views of Nantucket Sound. Ocean views from almost every room. Just moments from Oak Bluffs town beach and a sh... Read More
June 2025
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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
Oak Bluffs 8170
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Oak Bluffs
$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 Bedroom en-suite half bath, Window AC unit, second floor, BR2 Queen bedroom with additional convertible twin sofa, Window AC unit, Second Floor. Queen sleep sofa in the pass through den on first floor.
Oak Bluffs 820
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Oak Bluffs
$2,300.00 - $5,000.00 / per week
Beds 2 beds
Baths 1 Full, 1 Half Bath
Sleeps 5 sleeps
Oak Bluffs 820
Charming renovated two-bedroom Cottage. Open concept living and kitchen on the first floor, two bedrooms on the second floor. Window AC units in livi... Read More
June 2025
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1 2 3 4 5 6 $2300 7
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17 18 19 20 21 22 $4500 23
24 25 26 27 28 29 $3000 30
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BD1, Queen, Hall Bath with Shower, First Floor. BD2, Queen, Ensuite Bath with Jacuzzi and Shower, Washer Dryer, Private Deck, Second Floor. BD3, Queen, Hall Bath with Combination Tub Shower, Second Floor.
Oak Bluffs 8128
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Oak Bluffs
$6,500.00 - $7,500.00 / per week
Beds 3 beds
Baths 3 Full Bath
Sleeps 6 sleeps
Oak Bluffs 8128
A fantastic vacation rental in a quiet neighborhood in Oak Bluffs, roughly 5 minute drive to Circuit Avenue. This 3-bedroom home has been recently up... Read More
June 2025
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1 2 3 4 5 6 $6500 7
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BR1 Queen en suite with separate tub and shower, 1st floorBR2 Queen en suite with separate tub and shower, 1st floorHalf bath, 1st floorBR3 Queen en suite with tub/shower, 2nd floorBR4 Queen, 2nd floorBR5 (2)Twin beds, (1) set of bunk beds, 2nd floorHall bath with tub/shower, 2nd floorBR6 Queen, lower levelHalf bath, lower level
Oak Bluffs 857
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Oak Bluffs
$10,000.00 - $15,000.00 / per week
Beds 6 beds
Baths 4 Full, 1 Half Bath
Sleeps 14 sleeps
Oak Bluffs 857
Contemporary home sits on 1.4 acres. Perfect home for entertaining. This home has two full kitchens. Three primary suites two with Jacuzzi tubs. Fully... Read More
June 2025
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1 2 3 4 5 6 $11000 7
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