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!
130 properties available
Bellavista at the Seaview. Step inside this second-floor contemporary condo, completely renovated with a natural colors and lots of textures. The kitchen, living space, and primary en suite bedroom are all about the view. The second bedroom and hall bath create a semi-private suite for guests. Sit on the deck and watch the sunrise over Inkwell bea
Oak Bluffs 842
Bellavista at the Seaview. Step inside this second-floor contemporary condo, completely renovated with a natural colors and lots of textures. The kitc... Read More
Bellavista at the Seaview. Step inside this second-floor contemporary condo, completely renovated with a natural colors and lots of textures. The kitc... Read More
This contemporary home in Meadow View Farms offers plenty of space, inside and out. The open concept first floor includes a grand living room with cathedral ceilings on one end, and a first-floor en suite bedroom on the other. A screen porch sits just off of the living room and opens to a large outdoor patio with fire pit, grill and lounge area.
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Oak Bluffs 8121
This contemporary home in Meadow View Farms offers plenty of space, inside and out. The open concept first floor includes a grand living room with cat... Read More
This contemporary home in Meadow View Farms offers plenty of space, inside and out. The open concept first floor includes a grand living room with cat... Read More
The Preserve, located off County Road, offers luxurious accommodations with five modern, air-conditioned bedrooms, each equipped with an en-suite bathroom. The first-floor king suite features a spacious en-suite bathroom complete with a soaking tub and a separate shower. On the second floor, you will find four additional en-suite bedrooms along wit
Oak Bluffs 826
The Preserve, located off County Road, offers luxurious accommodations with five modern, air-conditioned bedrooms, each equipped with an en-suite bath... Read More
The Preserve, located off County Road, offers luxurious accommodations with five modern, air-conditioned bedrooms, each equipped with an en-suite bath... Read More
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 features a wall of windows that overlooks the backyard, allowing plenty of natural light to fill the space. The chef's kitchen is a highlight of the home with a massive 13-foot island that is perfect
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
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
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 relaxing vacation. A large chef's kitchen offers plenty of space for easy entertaining or organizing dinner for your beach picnic. The kitchen even has a dedicated beverage area and juice bar! The decor
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
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
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 island retreat. Enjoy plenty of space to relax and unwind with a spacious kitchen, living room, dining room, sitting room, and a sunlit TV room. Upstairs, three cozy bedrooms await, including the ensuit
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
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
Enjoy high end living, with commanding water views in this luxurious and meticulously detailed home with guest house. This home is filled with artwork, beautifully restored architectural detail, and incredible water views. The main house includes four bedrooms, split between two floors, while the one bedroom guest house includes a full kitchen, liv
Oak Bluffs 8154
Enjoy high end living, with commanding water views in this luxurious and meticulously detailed home with guest house. This home is filled with artwork... Read More
Enjoy high end living, with commanding water views in this luxurious and meticulously detailed home with guest house. This home is filled with artwork... 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 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 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 carousel, the renowned Flying Horses and many wonderful restaurants. Situated right on the bike path, this retreat boasts a private back patio and outdoor shower. Offering simplicity, comfort, and conv
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
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
Sprawling family compound tucked into the woods of Oak Bluffs. Entering into this beautifully landscaped property, the split rail fencing leads past the man made pond and double swing, with an old time porch looking out over the property below. Making your way up to the circular drive you arrive at the main and guest house entrance where you have p
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
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
A relaxing vacation awaits at this modern home overlooking the Lagoon. Tucked off of Barnes Road, the open concept layout offers stunning waterviews from the living, kitchen and dining areas, opening to a large outdoor deck. There is an ensuite bedroom on the main level and three additional bedrooms on the lower level as well as a media room with 6
Oak Bluffs 8104
A relaxing vacation awaits at this modern home overlooking the Lagoon. Tucked off of Barnes Road, the open concept layout offers stunning waterviews f... Read More
A relaxing vacation awaits at this modern home overlooking the Lagoon. Tucked off of Barnes Road, the open concept layout offers stunning waterviews f... Read More
This charming 3 Bedroom cottage-style Oak Bluffs home has been lovingly updated and is ready for your next vacation! The first of the 3 bedrooms is on the main floor located off of the open-concept living space with the kitchen beyond. Take advantage of the ample outdoor space relaxing on the deck or playing games on the lawn. Upstairs you will fin
Oak Bluffs 851
This charming 3 Bedroom cottage-style Oak Bluffs home has been lovingly updated and is ready for your next vacation! The first of the 3 bedrooms is on... Read More
This charming 3 Bedroom cottage-style Oak Bluffs home has been lovingly updated and is ready for your next vacation! The first of the 3 bedrooms is on... Read More
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