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!
125 properties available
This 2 story contemporary is located just outside Downtown Oak Bluffs with off-street parking for 2 cars. Immerse yourself in the hustle bustle of Circuit Ave or relax at home and enjoy the private outdoor space. Only 1 mile to the famous Inkwell Beach, this home has everything you need to enjoy your Martha's Vineyard vacation. The first floor offe
Oak Bluffs 813
This 2 story contemporary is located just outside Downtown Oak Bluffs with off-street parking for 2 cars. Immerse yourself in the hustle bustle of Cir... Read More
This 2 story contemporary is located just outside Downtown Oak Bluffs with off-street parking for 2 cars. Immerse yourself in the hustle bustle of Cir... Read More
Charming Oak Bluffs Retreat-This inviting three-bedroom, two-and-a-half-bath home offers a comfortable and relaxing setting for your Martha's Vineyard getaway. Enjoy spacious indoor living areas complemented by a bright sunroom and great outdoor space—perfect for lounging or dining al fresco. All three bedrooms are located on the second floor, prov
Oak Bluffs 8144
Charming Oak Bluffs Retreat-This inviting three-bedroom, two-and-a-half-bath home offers a comfortable and relaxing setting for your Martha's Vineyard... Read More
Charming Oak Bluffs Retreat-This inviting three-bedroom, two-and-a-half-bath home offers a comfortable and relaxing setting for your Martha's Vineyard... Read More
Just under a mile from downtown Oak Bluffs, this inviting 4-bedroom Cape combines comfort with a great location. Spend your days at Inkwell, Pay, or State Beaches, or head into town for ice cream, shopping, and dining—all just minutes away.
Back at the house, relax on the sunny deck, enjoy a quiet moment in the porch rocking chairs, or take advanta
Oak Bluffs 8814
Just under a mile from downtown Oak Bluffs, this inviting 4-bedroom Cape combines comfort with a great location. Spend your days at Inkwell, Pay, or S... Read More
Just under a mile from downtown Oak Bluffs, this inviting 4-bedroom Cape combines comfort with a great location. Spend your days at Inkwell, Pay, or S... Read More
This centrally located property is a true gem; surrounded by an array of flowering gardens and lush greenery that create a sense of serenity and tranquility. Inside, the Scandinavian, antique, and custom-handmade furnishings meld together with character and charm. The kitchen is a chef's dream, complete with a stunning Carrera marble countertop an
Oak Bluffs 8045
This centrally located property is a true gem; surrounded by an array of flowering gardens and lush greenery that create a sense of serenity and tranq... Read More
This centrally located property is a true gem; surrounded by an array of flowering gardens and lush greenery that create a sense of serenity and tranq... Read More
Contemporary home sits on 1.4 acres. Perfect home for entertaining. This home has two full kitchens. Many living areas with space to get away from the group. Three primary suites two with Jacuzzi tubs. Fully equipped kitchen. Large brick patio, complete with outdoor furniture and built-in stone BBQ pit. All bedrooms are equipped with Mini split or
Oak Bluffs 857
Contemporary home sits on 1.4 acres. Perfect home for entertaining. This home has two full kitchens. Many living areas with space to get away from the... Read More
Contemporary home sits on 1.4 acres. Perfect home for entertaining. This home has two full kitchens. Many living areas with space to get away from the... Read More
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 multiple living spaces, there is plenty of room to spread out. The open floorplan is spacious with a modern kitchen. There is also a bedroom with a queen bed and full bath on the main level. The fini
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
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
This affordable and well-maintained four-bedroom Cape is located approximately two miles from the center of Oak Bluffs and just a short distance from the town landing on Lagoon Pond. It is ideal for accommodating your extended family. The efficient kitchen provides access to the back deck, perfect for outdoor dining and gatherings. The home feature
Oak Bluffs 877
This affordable and well-maintained four-bedroom Cape is located approximately two miles from the center of Oak Bluffs and just a short distance from ... Read More
This affordable and well-maintained four-bedroom Cape is located approximately two miles from the center of Oak Bluffs and just a short distance from ... Read More
A classic Gambrel-style home refreshed for the 2025 season, this house offers ample space for entertaining and unwinding after a long day at the beach. The kitchen and bathrooms are newly renovated, coupled with an expansive sunroom which opens to the deck, creating a seamless flow between spaces both indoor and out. There is a first-floor bedroo
Oak Bluffs 8179
A classic Gambrel-style home refreshed for the 2025 season, this house offers ample space for entertaining and unwinding after a long day at the beac... Read More
A classic Gambrel-style home refreshed for the 2025 season, this house offers ample space for entertaining and unwinding after a long day at the beac... Read More
Your Vineyard Vacation awaits at this cozy 3 Bedroom, 2 Bath Cape Cod Style home located in the Lagoon Heights neighborhood of Oak Bluffs. The newly renovated kitchen flows seamlessly to the spacious backyard, perfect for gathering with friends and outdoor dining. In addition to the kitchen and living area, the first floor offers a bedroom with a q
Oak Bluffs 8158
Your Vineyard Vacation awaits at this cozy 3 Bedroom, 2 Bath Cape Cod Style home located in the Lagoon Heights neighborhood of Oak Bluffs. The newly r... Read More
Your Vineyard Vacation awaits at this cozy 3 Bedroom, 2 Bath Cape Cod Style home located in the Lagoon Heights neighborhood of Oak Bluffs. The newly r... Read More
Charming Oak Bluffs Bungalow - Nestled just off Upper Circuit Avenue, this delightful two-bedroom, two-bathroom bungalow captures the heart of Oak Bluffs living. Ideally located for Illumination Night, fireworks, and all the village's vibrant attractions, the home offers both comfort and convenience.
Enjoy warm summer evenings on the cozy front por
Oak Bluffs 836
Charming Oak Bluffs Bungalow - Nestled just off Upper Circuit Avenue, this delightful two-bedroom, two-bathroom bungalow captures the heart of Oak Blu... Read More
Charming Oak Bluffs Bungalow - Nestled just off Upper Circuit Avenue, this delightful two-bedroom, two-bathroom bungalow captures the heart of Oak Blu... Read More
Enjoy a wonderful vacation in this beautifully maintained and sun-filled retreat. Situated on a charming street near the lagoon and just about a mile from downtown Oak Bluffs, this home offers the perfect balance of relaxation and convenience. The home features modern amenities throughout, including an updated kitchen, central air conditioning and
Oak Bluffs 837
Enjoy a wonderful vacation in this beautifully maintained and sun-filled retreat. Situated on a charming street near the lagoon and just about a mile ... Read More
Enjoy a wonderful vacation in this beautifully maintained and sun-filled retreat. Situated on a charming street near the lagoon and just about a mile ... Read More
A six-bedroom, five-and-a-half-bath contemporary island home at Waterview Farms has direct access to the beach on Sengekontacket Pond. Sleeps twelve comfortably. The unique layout includes an attached guest house with a separate kitchenette and washer/dryer. Perfect for two families or friends looking for their individual space. The main house f
Oak Bluffs 8809
A six-bedroom, five-and-a-half-bath contemporary island home at Waterview Farms has direct access to the beach on Sengekontacket Pond. Sleeps twelve ... Read More
A six-bedroom, five-and-a-half-bath contemporary island home at Waterview Farms has direct access to the beach on Sengekontacket Pond. Sleeps twelve ... Read More
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