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, 1st floor hall bath of shower, BR2 (2)Twin beds, 2nd floorBR3 Queen, 2nd floor hall bath of tub/shower combo BR4 King, 2nd floor, en suite with separate tub and separate shower, 2nd floor
Oak Bluffs 811
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Oak Bluffs
$7,000.00 - $10,500.00 / per week
Beds 4 beds
Baths 3 Full Bath
Sleeps 8 sleeps
Rating 5 (1)
Oak Bluffs 811
Prepare to be mesmerized by the awe-inspiring sunsets visible from the large wraparound deck and several rooms of this immaculate Oak Bluffs home. Boa... Read More
June 2025
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          1 $10000 2
3 4 5 6 7 8 $10500 9
10 11 12 13 14 15 $10500 16
17 18 19 20 21 22 $8750 23
24 25 26 27 28 29 $8750 30
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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 en suite with tub/shower, 1st floorBR2 (2)Twin beds 1st floorHall bath with tub/shower, 1st floor
Oak Bluffs Sea View Condo 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 Sea View Condo 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 King en suite with separate shower and soaking tub, 1st floorBR2 Queen en suite with tub/shower, 2nd floorBR3 Queen en suite with shower stall, 2nd floorBR4 Double en suite with tub and french shower, 2nd floorBR5 (2)Twin beds en suite with tub/shower, 2nd floor (over the garage with private entrance)Half baths, 1st and 2nd floorsLaundry facili
Oak Bluffs 846
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Oak Bluffs
$14,500.00 - $32,025.00 / per week
Beds 5 beds
Baths 5 Full, 1 Half Bath
Sleeps 10 sleeps
Oak Bluffs 846
The "Preserve" off of County Road at its finest! Five modern bedrooms, fully air conditioned, expanded farmhouse with inspiration and fixtures from Re... Read More
June 2025
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1 2 3 4 5 6 $22500 7
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15 16 17 18 19 20 $24500 21
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BR1 Queen en suite with shower stall, 1st floorHall bath with tub and french shower, 1st floorBR2 Queen en suite with shower stall, 2nd floorBR3 Queen, 2nd floorBR4 (2)Twin beds, 2nd floorHall bath with tub/shower, 2nd floorHalf bath, lower levelGuest house: BR5 Queen en suite with tub/shower, 1st floor
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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BR1 King en suite with separate tub and shower, 1st floorBR2 King en suite with shower, 2nd floorBR3 (2)Twin beds, 2nd floorBR4 (2)Twin beds, 2nd floorHall bath with tub/shower, 2nd floorLaundry facilities, 1st floorHalf bath, 1st floor
Oak Bluffs 8141
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Oak Bluffs
$12,000.00 - $22,000.00 / per week
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps 8 sleeps
Oak Bluffs 8141
Don't miss out on this amazing vacation opportunity on Martha's Vineyard! You can relax in the comfortable living room and enjoy the beautiful view th... Read More
June 2025
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1 2 3 4 5 6 $12000 7
8 9 10 11 12 13 $12000 14
15 16 17 18 19 20 $12500 21
22 23 24 25 26 27 $16000 28
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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
$4,500.00 - $8,000.00 / 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 $4500 7
8 9 10 11 12 13 $4500 14
15 16 17 18 19 20 $4500 21
22 23 24 25 26 27 $4500 28
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July 2025
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    1 2 3 4 $7500 5
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13 14 15 16 17 18 $7500 19
20 21 22 23 24 25 $7500 26
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17 18 19 20 21 22 $8000 23
24 25 26 27 28 29 $7500 30
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BR1 Queen en suite with tub/shower, 1st floorBR2 (2)Twin beds, 1st floorHall bath with tub/shower, 1st floor
Oak Bluffs Sea View Condo 835
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Oak Bluffs
$1,900.00 - $5,100.00 / per week
Beds 2 beds
Baths 2 Full Bath
Sleeps 4 sleeps
Rating 4.5 (2)
Oak Bluffs Sea View Condo 835
Welcome to this charming two bed, two bath corner end unit condo located in the heart of Oak Bluffs, just steps away from the Town Beach (Ink Well). E... Read More
June 2025
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15 16 17 18 19 20 $2050 21
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    1 2 3 4 $4000 5
6 7 8 9 10 11 $4500 12
13 14 15 16 17 18 $4500 19
20 21 22 23 24 25 $4500 26
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BR1 (2)Twin beds, 2nd floorBR2 King, 2nd floorBR3 (2)Twin beds, 2nd floorBR4 King, 2nd floorHall bath with tub/shower, 2nd floorHall bath with tub/shower, 1st floorHall bath with tub/shower, lower levelLaundry facilities, lower level
Oak Bluffs 806
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Oak Bluffs
$6,000.00 - $7,000.00 / per week
Beds 4 beds
Baths 3 Full Bath
Sleeps 8 sleeps
Rating 4.5 (2)
Oak Bluffs 806
Located in the heart of Oak Bluffs, your vacation will be as action packed or relaxing as you want it! Roomy and comfortable, this home has space for ... Read More
June 2025
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1 2 3 4 5 6 $6000 7
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BR1 Queen en suite with shower stall, AC 1st floorBR2 Twin bed, 1st floorHall bath with tub, 1st floorBR3 (2)Twin beds, 2nd floorBR4 Queen, 2nd floorBR5 Queen, 2nd floorHall bath with tub/shower, 2nd floor
Oak Bluffs 8124
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Oak Bluffs
$7,500.00 / per week
Beds 5 beds
Baths 3 Full Bath
Sleeps 9 sleeps
Rating 3 (1)
Oak Bluffs 8124
Charming five bedroom gingerbread beach cottage is strategically located on Ocean Park in the center of Oak Bluffs. Birds eye view of all that is happ... 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
June 2025
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BR1 Double, 2nd floorBR2 Double, 2nd floorHall bath with tub/shower, 1st floor
Oak Bluffs 8081
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Oak Bluffs
$3,500.00 / per week
Beds 2 beds
Baths 1 Full Bath
Sleeps 4 sleeps
Oak Bluffs 8081
Escape to a charming oasis in Oak Bluffs with this classic two-bedroom cottage, perfect for a relaxing vacation near beautiful Pay Beach, Inkwell, and... Read More
June 2025
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1 2 3 4 5 6 $3500 7
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    1 2 3 4 $3500 5
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13 14 15 16 17 18 $3500 19
20 21 22 23 24 25 $3500 26
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