Oak Bluffs
.jpg)
https://sandpiperrental.icnd-cdn.com/images/resorts/OB1.jpg
https://sandpiperrental.icnd-cdn.com/images/resorts/OB.jpg
https://sandpiperrental.icnd-cdn.com/images/resorts/Craft-1-2.jpg
https://sandpiperrental.icnd-cdn.com/images/resorts/DJI_0251_hdr (1).jpg
https://sandpiperrental.icnd-cdn.com/images/resorts/Inkwell Drone .jpg
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!
124 properties available
This charming waterfront two story Cape sits atop the Lagoon bluffs. Boasts spectacular sunsets and panoramic waterfront views of Lagoon, outer Vineyard Haven Harbor and Cape Cod from the patios, living room, dining room and two upstairs bedrooms. Stairs down to private beach. You are just minutes to the center of Oak Bluffs village. It truly is a
Oak Bluffs 805
This charming waterfront two story Cape sits atop the Lagoon bluffs. Boasts spectacular sunsets and panoramic waterfront views of Lagoon, outer Vineya... Read More
This charming waterfront two story Cape sits atop the Lagoon bluffs. Boasts spectacular sunsets and panoramic waterfront views of Lagoon, outer Vineya... 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
Welcome to your dream vacation home! This stunning 4 bedroom, 2-story home is located on the lagoon and offers breathtaking water views and stunning sunsets. With more than 150 feet of private beach frontage, you'll enjoy privacy and ample space to relax and unwind. TDesigned for comfort and convenience, the home features two en suite bedrooms on t
Oak Bluffs 824
Welcome to your dream vacation home! This stunning 4 bedroom, 2-story home is located on the lagoon and offers breathtaking water views and stunning s... Read More
Welcome to your dream vacation home! This stunning 4 bedroom, 2-story home is located on the lagoon and offers breathtaking water views and stunning s... Read More
This spacious Cape-style home is located in a quiet residential neighborhood in Oak Bluffs, just a short drive to town and an easy walk to the Lagoon—perfect for kayaking and enjoying beautiful sunset views. The home is clean and fully equipped, featuring a first-floor primary bedroom and a small office that offers a private retreat. Additional bed
Oak Bluffs 8178
This spacious Cape-style home is located in a quiet residential neighborhood in Oak Bluffs, just a short drive to town and an easy walk to the Lagoon—... Read More
This spacious Cape-style home is located in a quiet residential neighborhood in Oak Bluffs, just a short drive to town and an easy walk to the Lagoon—... Read More
This comfortable three-bedroom vacation home is centrally located along the bike path and is approximately four miles from the charming towns and beautiful beaches of Edgartown, Oak Bluffs, and Vineyard Haven. The house features cozy furnishings and lovely wood floors on both the first and second levels.
Amenities include high-speed wireless intern
Oak Bluffs 860
This comfortable three-bedroom vacation home is centrally located along the bike path and is approximately four miles from the charming towns and beau... Read More
This comfortable three-bedroom vacation home is centrally located along the bike path and is approximately four miles from the charming towns and beau... 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
Sparkling Vineyard reverse level cottage has the fresh airy updates with painted white shiplap for wall decor, hardwoods and stainless steel to complete this modern beach house. From the open floor plan of dining, living and kitchen with walk out to the deck enjoy entertaining and keeping everyone together all on the second floor as well as a half
Oak Bluffs 8011
Sparkling Vineyard reverse level cottage has the fresh airy updates with painted white shiplap for wall decor, hardwoods and stainless steel to comple... Read More
Sparkling Vineyard reverse level cottage has the fresh airy updates with painted white shiplap for wall decor, hardwoods and stainless steel to comple... Read More
Designed by renowned architect Patrick Ahearn, this house offers a contemporary interpretation of a Martha's Vineyard Cape. Evoking the grandeur of an equestrian estate, this six-bedroom, nine-bath home is perched on a hill, overlooking a pond and situated on nearly four acres in the Preserve. The impeccably designed interiors create a sense of pla
Oak Bluffs 8168
Designed by renowned architect Patrick Ahearn, this house offers a contemporary interpretation of a Martha's Vineyard Cape. Evoking the grandeur of an... Read More
Designed by renowned architect Patrick Ahearn, this house offers a contemporary interpretation of a Martha's Vineyard Cape. Evoking the grandeur of an... 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 this sprawling property packed with activities for all, and fantastic views of the ocean. This home includes a spacious main house, guest house, and oversized deck, perfect for entertaining, grilling and memorable evenings. The nearby guest house includes a king bed, kitchenette, and full bath. This home includes many amenities for all to enj
Oak Bluffs 812
Enjoy this sprawling property packed with activities for all, and fantastic views of the ocean. This home includes a spacious main house, guest house,... Read More
Enjoy this sprawling property packed with activities for all, and fantastic views of the ocean. This home includes a spacious main house, guest house,... Read More
Situated just about a mile from Oak Bluffs downtown and town beaches, is this charming four bedroom two bathroom home. It is comfortably furnished equipped with air conditioning, two sitting rooms, and updated kitchen and bathrooms. The fully equipped kitchen offers stainless steel appliances, gorgeous countertops, a butcher block island and bonus
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
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
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
Tell us what you're looking for and someone will contact you with available options.
