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 137 properties available
BR1 King or two twins, 1st floorBR2 Queen, 1st floorHall bath with tub/shower, 1st floorBR3 Queen, 2nd floorBR4 Double & Twin Bed, 2nd floorHall bath with tub/shower, 2nd floorLaundry facilities, 1st floor
Hot HOT 12
Oak Bluffs Pet Friendly
$6,000.00 - $7,000.00 / per week
Beds 4 beds
Baths 2 Full Bath
Sleeps 8 sleeps
Rating 5 (1)
Oak Bluffs 8132
Situated just about a mile from Oak Bluffs downtown and town beaches, is this charming four bedroom two bathroom home. It is comfortably furnished equ... Read More
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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
$1,900.00 - $5,100.00 / per week
Beds 2 beds
Baths 2 Full Bath
Sleeps 4 sleeps
Rating 4.5 (2)
Oak Bluffs 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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    1 2 3 4 $4000 5
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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
$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 King, 2nd floorBR2 Queen, 2nd floorHall bath with shower stall, 2nd floorHalf Bath and Laundry facilities, 1st floor
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
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BR1 Double, 1st floorBR2 (2)Twin beds, 1st floorHall bath with tub/shower, 1st floorBR3 Queen, 2nd floorBR4 Queen and (2)Twin beds, 2nd floorHall bath with tub/shower, 2nd floor AC Window units in all bedrooms.
Oak Bluffs
$4,360.00 / per week
Beds 4 beds
Baths 2 Full Bath
Sleeps 8 sleeps
Oak Bluffs 877
This affordable and well-maintained four bedroom Cape located approximately two miles from center of Oak Bluffs and short distance to the town landing... Read More
June 2025
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1 2 3 4 5 6 $4360 7
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BR1 Double en suite with Shower and Soaking Tub Combo, First FloorBR2 Queen, First FloorBR3 Queen, First FloorHall Bath with Shower, First FloorAdditional Sleeping Double Sofa-bed en suite with Shower, Lower LevelBR4 Double, guesthouseBR5 Double Sofa Bed, guesthouseHall Bath with Shower, guesthouseLaundry Facilities in main and guest houses
Oak Bluffs
$4,300.00 - $8,000.00 / per week
Beds 5 beds
Baths 4 Full Bath
Sleeps 12 sleeps
Oak Bluffs Main and Guest House 8043
Centrally located main and guest houses are a true gem; surrounded by an array of flowering gardens and lush greenery that create a sense of serenity ... Read More
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BR1 King en suite with soaking tub and shower, 1st floorBR2 King en suite with shower stall, 2nd floorBR3 Queen en suite with shower, 2nd floorBR4 Double with trundle en suite with tub/shower, 2nd floorBR5 (2)Bunk beds and double bed en suite with shower stall, lower levelHall bath, lower levelBR6 (2)Bunk beds and double bed en suite with shower st
Hot HOT 32
Oak Bluffs
$17,500.00 - $34,000.00 / per week
Beds 6 beds
Baths 9 Full Bath
Sleeps 16 sleeps
Rating 5 (1)
Oak Bluffs 8168
Designed by renowned architect Patrick Ahearn, this house is meant to be a contemporary interpretation of a Martha's Vineyard Cape. Evoking the grand... Read More
June 2025
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1 2 3 4 5 6 $25000 7
8 9 10 11 12 13 $25000 14
15 16 17 18 19 20 $27500 21
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BR1 Queen en suite with separate tub and shower, 2nd floorBR2 Queen, 2nd floorBR3 (2)Twin beds, 2nd floorHall bath with tub/shower, 2nd floorBR4 Queen and (5)Twin beds, 3rd floorBR5 Queen en suite with shower stall, Lower LevelHalf bath, 1st floor
Oak Bluffs
$7,350.00 - $7,950.00 / per week
Beds 5 beds
Baths 3 Full, 1 Half Bath
Sleeps 13 sleeps
Rating 4.5 (2)
Oak Bluffs 8109
Enjoy this expansive five bedroom home, ideal for extended family or friends. Spanning four levels, there is ample space for everyone to spread out. T... Read More
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BR1 Queen en suite with shower, 1st floorBR2 Queen en suite with tub/shower, 2nd floorBR3 (2)Bunk beds, 2nd floor
Oak Bluffs
$6,800.00 - $9,000.00 / per week
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps 8 sleeps
Rating 5 (1)
Oak Bluffs 8815
An extensive redesign and perhaps the most dramatic transformation yet! This wonderful downtown cottage has been restored in a way that reflects the c... Read More
June 2025
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1 2 3 4 5 6 $6800 7
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17 18 19 20 21 22 $8000 23
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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
June 2025
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1 2 3 4 5 6 $6293 7
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22 23 24 25 26 27 $6993 28
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17 18 19 20 21 22 $7693 23
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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
$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 2 3 4 5 6 $7500 7
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22 23 24 25 26 27 $8200 28
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    1 2 3 4 $8200 5
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17 18 19 20 21 22 $8750 23
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BR1 Queen, First Floor with Half BathBR2 Queen, First FloorBR3 (2) Twin Beds, First FloorHall Bath with Tub/Shower Combo, First Floor
Hot HOT 10
Oak Bluffs Pet Friendly
$3,950.00 - $5,000.00 / per week
Beds 3 beds
Baths 1 Full, 1 Half Bath
Sleeps 6 sleeps
Oak Bluffs 8161
Discover the charm of this single-story rental home, perfect for your next vacation. Fully equipped with new furniture and updated bathrooms, this coz... Read More
June 2025
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1 2 3 4 5 6 $3950 7
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    1 2 3 4 $3950 5
6 7 8 9 10 11 $3950 12
13 14 15 16 17 18 $3950 19
20 21 22 23 24 25 $4100 26
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17 18 19 20 21 22 $3950 23
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