Oak Bluffs
.jpg)
https://sandpiperrental.icnd-cdn.com/images/resorts/Craft-8-2.jpg
https://sandpiperrental.icnd-cdn.com/images/resorts/OB1.jpg
https://sandpiperrental.icnd-cdn.com/images/resorts/DJI_0874.jpg
https://sandpiperrental.icnd-cdn.com/images/resorts/OB Harbor Aerial.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
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
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
Come experience Oak Bluffs in this quintessential five bedroom gingerbread cottage reminiscent of times gone by. Just a stroll down the street to Inkwell Beach or into town. The five bedrooms are located on the second floor and share two bathrooms. There is an additional half bath and an outdoor shower. Your favorite part of your vacation will be
Oak Bluffs 833
Come experience Oak Bluffs in this quintessential five bedroom gingerbread cottage reminiscent of times gone by. Just a stroll down the street to Inkw... Read More
Come experience Oak Bluffs in this quintessential five bedroom gingerbread cottage reminiscent of times gone by. Just a stroll down the street to Inkw... Read More
This centrally air conditioned four bedroom traditional style home is located within the Bayes Hill neighborhood. A spacious, quiet and well maintained area in Oak Bluffs with beautiful curb appeal. This property has a well equipped kitchen, spacious living area, deck, and an area for those who need to work from home. There is an enclosed outdoor
Oak Bluffs 8101
This centrally air conditioned four bedroom traditional style home is located within the Bayes Hill neighborhood. A spacious, quiet and well maintai... Read More
This centrally air conditioned four bedroom traditional style home is located within the Bayes Hill neighborhood. A spacious, quiet and well maintai... Read More
A Frank Lloyd Wright-inspired home in Harthaven with a reverse style 3-bedroom main house and a 2-bedroom guest house offers an abundance of privacy and a spectacular location. The open concept living spaces open to both the screened porch and expansive deck, which creates an abundance of living space and ample opportunity to relax and soak in all
Oak Bluffs 8010
A Frank Lloyd Wright-inspired home in Harthaven with a reverse style 3-bedroom main house and a 2-bedroom guest house offers an abundance of privacy a... Read More
A Frank Lloyd Wright-inspired home in Harthaven with a reverse style 3-bedroom main house and a 2-bedroom guest house offers an abundance of privacy a... Read More
Centrally located, custom colonial, in Oak Bluffs. Cook a true Vineyard feast from the wonderfully designed chef's kitchen with Wolf Gas stove. The kitchen flows seamlessly into the living area where you may eat at the dining table that looks out to the back yard. Or for those evening cookouts, the rear deck is perfect. For those "working" on va
Oak Bluffs 832
Centrally located, custom colonial, in Oak Bluffs. Cook a true Vineyard feast from the wonderfully designed chef's kitchen with Wolf Gas stove. The k... Read More
Centrally located, custom colonial, in Oak Bluffs. Cook a true Vineyard feast from the wonderfully designed chef's kitchen with Wolf Gas stove. The k... 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
Luxurious waterfront four bedroom , all private bathrooms, fully air conditioned, by their own individual high efficiency ductless mini-split units, beach house with state of the art kitchen, gorgeous and comfortable furnishings throughout, fabulous decking to outdoor entertaining overlooking the Lagoon Pond. Most every room in the house has a wate
Oak Bluffs 8151
Luxurious waterfront four bedroom , all private bathrooms, fully air conditioned, by their own individual high efficiency ductless mini-split units, b... Read More
Luxurious waterfront four bedroom , all private bathrooms, fully air conditioned, by their own individual high efficiency ductless mini-split units, b... Read More
Ideal Oak Bluffs location! This charming Victorian gingerbread beach house features a fabulous verandah with plenty of comfortable outdoor furniture and a porch swing, perfect for conversation and relaxation. The highlight of this rental property is its proximity—just one block away from Inkwell Beach. Inside, you'll find a cozy living room with a
Oak Bluffs 8131
Ideal Oak Bluffs location! This charming Victorian gingerbread beach house features a fabulous verandah with plenty of comfortable outdoor furniture a... Read More
Ideal Oak Bluffs location! This charming Victorian gingerbread beach house features a fabulous verandah with plenty of comfortable outdoor furniture a... Read More
Newly furnished, four-bedroom property in the Meadow View Farms. Enter into a large foyer with a sitting room to the left and a dining area on the right. A den is set off to the side of the dining area. The large well-equipped kitchen looks out to the vaulted ceiling main living area with two French doors leading to the outside deck (new gas grill
Oak Bluffs 8092
Newly furnished, four-bedroom property in the Meadow View Farms. Enter into a large foyer with a sitting room to the left and a dining area on the rig... Read More
Newly furnished, four-bedroom property in the Meadow View Farms. Enter into a large foyer with a sitting room to the left and a dining area on the rig... Read More
Pirate's Reef is a beautifully decorated residence that offers five spacious bedrooms (two primary suites!) with four and a half bathrooms and accommodates up to twelve guests. This is the PERFECT vacation home! It's nestled behind the historic Shearer Cottage on a quiet lane in East Chop, just minutes away from all the charm and activities that Oa
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
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
This rental home is a true gem, nestled in a peaceful, natural setting on a private, dead-end road. The exterior of the home features a large back deck and a screened-in porch off the kitchen, providing extra space for outdoor relaxation and enjoyment.
Inside, you'll find a cozy and comfortable living space with high ceilings, hardwood floors, and
Oak Bluffs 830
This rental home is a true gem, nestled in a peaceful, natural setting on a private, dead-end road. The exterior of the home features a large back dec... Read More
This rental home is a true gem, nestled in a peaceful, natural setting on a private, dead-end road. The exterior of the home features a large back dec... Read More
Prime Oak Bluffs location in a serene setting. This home has plenty of room to spread out and enjoy your vacation. The main level has a generous and spacious kitchen that opens to both the dining and living areas. Off of the dining area is a lovely screened porch, perfect for that extra space. There is also a bedroom and full bath, along with laund
Oak Bluffs 802
Prime Oak Bluffs location in a serene setting. This home has plenty of room to spread out and enjoy your vacation. The main level has a generous and s... Read More
Prime Oak Bluffs location in a serene setting. This home has plenty of room to spread out and enjoy your vacation. The main level has a generous and s... Read More
Tell us what you're looking for and someone will contact you with available options.
