Oak Bluffs

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 139 properties available
BR1 King en suite with tub and shower, 1st floorBR2 Double with Twin Trundle, shared hall bath with shower / tub combo, 2nd floorBR3 Queen, shared hall bath with shower / tub combo, 2nd floorBR4 Queen with Twin bed with Twin Trundle, shared hall bath with shower / tub combo, 2nd floorHalf bath, 1st floorFull bath, lower level
Oak Bluffs
$10,000.00 - $12,000.00 / per week
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps 10 sleeps
Oak Bluffs 849
Convenient to downtown Oak Bluffs and beaches beyond, this stylish and updated home offers room to roam, both inside and out. This home has an open fl... Read More
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BR2 (2)Double beds,lower level, BR3 Oversized twin bed, 2nd floor BR 4 King 2nd floor, Hall bath with tub/shower, 2nd floor
Oak Bluffs
$5,000.00 - $8,500.00 / per week
Beds 4 beds
Baths 2 Full Bath
Sleeps 8 sleeps
Rating 4 (1)
Oak Bluffs 821
A well built three bedroom custom cape is just minutes to the village of Oak Bluffs. As you enter this home you are graced with cathedral ceilings equ... Read More
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BR1 King en suite with shower stall, 1st floorBR2 King en suite with tub/shower, 2nd floorBR3 Twin and queen sofa bed en suite with tub/shower, 2nd floorBR4 Double and twin bed, 2nd floorBR5 Queen and twin bed, 2nd floorHall bath with tub/shower, 2nd floorHalf bath, 1st floorLaundry facilities, lower level
Oak Bluffs
$5,500.00 - $13,800.00 / per week
Beds 5 beds
Baths 4 Full, 1 Half Bath
Sleeps 12 sleeps
Oak Bluffs 8129
Pirate's Reef is a beautifully decorated residence that offers five spacious bedrooms (two primary suites!) with four and a half bathrooms and accommo... Read More
June 2025
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BR1 King, First FloorBR2 (2) Twin Beds, First FloorHall Bath with Tub/Shower, First Floor
Oak Bluffs
$2,500.00 - $2,800.00 / per week
Beds 2 beds
Baths 1 Full Bath
Sleeps 4 sleeps
Oak Bluffs 8021
Charming and pristine cottage nestled just over a mile from both Oak Bluffs Beaches and the vibrant town of Oak Bluffs, home to the country's oldest c... Read More
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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
$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, 2nd floorHall bath with shower stall, 2nd floorBR2 King en suite with separate tub and shower, 2nd floorBR3 Queen, 2nd floorBR4 (2)Twin beds, 2nd floorHall bath with tub/shower, 2nd floorHalf bath, 1st floor
Oak Bluffs
$5,500.00 - $9,000.00 / per week
Beds 4 beds
Baths 3 Full Bath
Sleeps 8 sleeps
Oak Bluffs 819
This neighborhood is the best kept secret with an Oak Bluffs address. Down a quiet road, yet on a road with easy access to Oak Bluffs, Edgartown, West... Read More
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BR1 Queen, 1st floorBR2 Queen, 1st floorHall bath with shower stall, 1st floorHalf bath, 1st floorBR3 Queen, lower level BR4 Queen, lower levelHall bath with tub/shower, lower levelBR5 (3)Double beds and (2)twin beds, loft
Oak Bluffs
$5,000.00 - $12,000.00 / per week
Beds 5 beds
Baths 2 Full, 1 Half Bath
Sleeps 12 sleeps
Rating 5 (1)
Oak Bluffs 822
This four bedroom plus loft Oak Bluffs property is nestled in a very well kept and peaceful association called Sengekontacket. Its association offers ... Read More
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BR1 Queen en suite with separate tub and shower, 2nd floorBR2 King, 3rd floorHall bath with separate tub and shower, 3rd floorBR3 Double, 1st floorBR4 Double, 1st floorHall bath with tub/shower, 1st floorGuest house: BR5 Queen, 2nd floorHall bath with tub/shower, 1st floor
Oak Bluffs
$8,000.00 - $20,000.00 / per week
Beds 5 beds
Baths 5 Full Bath
Sleeps 10 sleeps
Rating 5 (1)
Oak Bluffs 878
Sprawling family compound tucked into the woods of Oak Bluffs. Entering into this beautifully landscaped property, the split rail fencing leads past t... Read More
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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
$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
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BR1 King en suite with shower stall, 1st floorBR2 Queen, 1st floorBR3 Double, 1st floor BR4 (2)Twin beds, 1st floorHall bath with tub/shower, 1st floorDouble sofa bed, 1st floor sitting roomHalf bath, 2nd floor
Oak Bluffs
$5,500.00 - $12,500.00 / per week
Beds 4 beds
Baths 2 Full, 1 Half Bath
Sleeps 8 sleeps
Rating 4.6 (3)
Oak Bluffs 8120
Historic Cape reverse set up, with living area, kitchen and powder room on the upper level with spectacular ocean views and the remaining living space... Read More
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BR1 King en suite with shower stall, 1st floorBR2 King en suite with tub/shower, 1st floorBR3 Queen and (2)Twin beds en suite with shower stall, lower levelGuest House: BR4 King, 1st floorBR5 (2)Twin beds, 1st floorHall bath with shower stall, 1st floorLaundry facilities, main house lower level
Oak Bluffs
$10,000.00 - $18,000.00 / per week
Beds 5 beds
Baths 4 Full Bath
Sleeps 12 sleeps
Rating 4 (1)
Oak Bluffs 8111
Oak Bluffs waterfront Main and Guest house with plenty of room to spread out and find your own peace and tranquility while you enjoy the spectacular v... Read More
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BR1 King, Second FloorHall Bath with Shower Tub Combo, Second FloorBR2 Queen, Second FloorBR3 Queen, First FloorHall Bath with Shower Tub Combo, First FloorBR4 Queen, First Floor
Oak Bluffs Pet Friendly
$4,893.00 - $7,693.00 / per week
Beds 4 beds
Baths 2 Full Bath
Sleeps 8 sleeps
Oak Bluffs 8028
Looking for a cozy and inviting house for rent in Oak Bluffs? This beautiful property is located just a mile and a half from the beach, making it the ... Read More
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