Oak Bluffs Vacation Rentals

Discover our latest vacation rentals in the Martha's Vineyard town of Oak Bluffs. Look through a variety of listings including beautiful oceanfront homes, luxury estates, cottages, and more! 

To get more information on Martha's Vineyard vacation rentals in Oak Bluffs:

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Rental Price$7,000 to $14,500

Rental ID 126030

  • RTR Vacation Rental
  • Lease $7,000 to $14,500
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 5

The Weku House is a luxury, 5,000 square foot home located in the beautiful town of Oak Bluffs on Martha’s Vineyard. Originally built in the year 2000, this home was fully renovated in 2015. Elegantly decorated with designer furnishings and interior appointments, the meticulous attention-to-detail makes this home a unique vacation retreat. With a total of 5 bedrooms and 5 1/2 baths, the home features sleeping accommodations that include two master king suites with ensuite bathrooms, a bedroom with two twin beds, and another spacious queen-sized guest bedroom. Additionally featured is an attached 720 square foot private apartment. "The Apartment" at Weku House features a fully equipped kitchen with Bosch appliances, a queen-sized bedroom, private bathroom, in-unit washer and dryer and an open living and dining room. There is also a private deck with bistro seating. A most popular feature of the home is the spectacularly finished basement, which includes state-of-the-art entertainment come rain-or-shine. Features include: a fitness room, a Play Zone with PlayStation 4, and Wii gaming consoles, a 40 inch 4K high-definition TV and a multitude of board games. Also in the basement is a stunning custom designed bar area with icemaker, dishwasher, microwave and a Hi Def TV overlooking a customized pool table. A home theater with a 70 inch 4K high definition TV and surround sound complete this entertainment space. Add to all of this a 1.3-acre setting, a serene front porch with rocking chairs overlooking beautifully landscaped grounds and a rear deck with dining and seating areas surrounding a rectangular gas fire table, and a gas-powered outdoor grill. With great pride, we welcome you to The Weku House.

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Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$6,300 to $11,095

Rental ID 141578

  • RTR Vacation Rental
  • Lease $6,300 to $11,095
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2

Endless views of the ocean, directly across from the water, and steps away from a sandy beach excellent for swimming. Gorgeously remodeled last summer (2018) and designed with a sophisticated California-meets-MV feel inside, our welcoming, centrally-air-conditioned, 4 bedroom house sleeps 10 and is a rarity in this area. Blonde wood wide plank flooring, new kitchen, new doors & windows, mattresses, and appliances including dishwasher, gas range, French door refrigerator with ice maker and a king size bed in a larger than usual (for OB) master BR. The house is airy and uncluttered, with a wide 3-sided wraparound porch, perfect for watching the annual fireworks, dining outside or watching the world go by. 4 well appointed bedrooms -- one downstairs and three upstairs (including a larger bedroom with a queen & 2 twins which is perfect for sharing). Second-story deck off the master bedroom offers views of the ocean, as well as Farm Pond. A second porch off the second & third upstairs bedrooms also has ocean views. Two sets of French doors from the kitchen and dining area open out to a larger portion of the deck and stunning ocean views. Updated bathrooms (glass-door subway tile walk-in shower downstairs, a deep soaking tub upstairs), wide porches to relax and dine on, and an open and connected feeling downstairs (a wood topped bar/island connects guests to the dining area and the kitchen, open french doors connect it all to the deck and the outdoor seating/dining). The house is set back from the road by a generous lawn, and is a very short distance (a few houses) to the bike path that runs along the island s edge & State Beach and into Edgartown, and within easy walking distance of both the Oak Bluffs ferry docking and the shops and restaurants in town and along the harbor, so you ll never have to search for a parking space to dine in-town in the high season. There s a large dining table inside & barbecue and additional outdoor seating/dining table on the porch, TV (televisions in the living room and the master BR). 1 king bed, 2 queen beds, 1 full sized bed, and 2 twin beds. Additionally, upon request/discussion, there is a back guest cottage aka "The Nest". The Nest has a good size upstairs bedroom (offering what is then a 5th BR); queen bed and a twin bed (sharing the same room), a deck off the bedroom that has water views (ocean and Farm Pond),

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$6,000 to $13,500

Rental ID 139055

  • RTR Vacation Rental
  • Lease $6,000 to $13,500
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 4

Luxury home located in a parkland setting in Sengekontacket - peaceful and serene yet close to downtown Oak Bluffs and the rest of the Vineyard. This new construction home has a large gourmet kitchen and wide open space adjacent dining and living areas. It is perfect layout for families to gather and socialize. The first floor opens onto a stone patio and grassy landscaped yard - ideal for grilling and outdoor entertaining. There is a large en-suite master bedroom on the first floor. Sliding doors open to a private back deck - perfect for enjoying your morning coffee. Four additional bedrooms are located on the second floor. Queen sized bedroom with private bath. Full sized bedroom with private bath. Two bedrooms with two twin beds give your family multiple sleeping arrangements. There is an association boat launch that is available for your kayaks.

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%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$3,000 to $6,000

Rental ID 135069

  • RTR Vacation Rental
  • Lease $3,000 to $6,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 1

Leave your worries and your car behind - this picture perfect Vineyard beach house is steps from downtown Oak Bluffs, the sandy beach and a few short blocks from the ferry. Recently renovated and restored, four bedrooms and one full and two half baths, offering the perfect juxtaposition of cottage charm and modern beach chic; the style is incredibly livable, comfortable, colorful and relaxed - all vital ingredients to the perfect vacation.

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$3,500 to $6,000

Rental ID 132319

  • RTR Vacation Rental
  • Lease $3,500 to $6,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 3

Beautiful newly built 4 bedroom home, spacious living room with fireplace, eat in kitchen and entertainment room. The home is just two blocks away from the town and four blocks from the beach.

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$4,000 to $5,500

Rental ID 132307

  • RTR Vacation Rental
  • Lease $4,000 to $5,500
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 4

We welcome you to enjoy our spacious and comfortable home. It s a beautiful 5 BR, 4.5 bath Oak Bluffs home with modern conveniences and nestled in an idyllic, secluded location. Perfect for large family gatherings. The amenities include AC, granite kitchen counter tops, breakfast bar, W/D, WiFi, five flat screen cable TVs, DVD & VHS players, gas grill, outdoor shower, hardwood floors and wood-burning fireplace for ambiance or a chilly evening. Large dining room table (comfortably seats 8) and fully equipped kitchen includes dishwasher and stock pots for steaming your crabs, clams & lobsters for that ultimate Vineyard experience. The house is located on a quiet street, has a private back yard and 2 large decks for casual dining and relaxing. Close to everything - town (5 minute drive/15 min walk) , harbor, ferry, shops, and restaurants.

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$3,500 to $4,800

Rental ID 119948

  • RTR Vacation Rental
  • Lease $3,500 to $4,800
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 3

Float your little boat, kayak, raft or canoe from this lovely homestead on Fresh Pond in Oak Bluffs. Built in 2004, this handsome colonial on 1.5 acres features four bedrooms, two living spaces, well-appointed kitchen with granite countertops, office, screened-in porch, mahogany deck, ample parking and tranquil pond views. Close to bike path, conservation trail and Farm Neck Golf Club. Within a ten-minute drive to downtown.

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental ID 116772

  • RTR Vacation Rental
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2
  • Half Baths 1

Marvelous vintage cottage remodeled to perfection in 1985. Waterfront location with private beach in front along with a 120 foot dock. Professionally decorated interior. Magical setting.

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$3,150 to $4,950

Rental ID 116762

  • RTR Vacation Rental
  • Lease $3,150 to $4,950
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2

This charming, recently renovated waterfront two-story cape situated atop the lagoon bluffs boasts spectacular sunsets and panoramic 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.

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$3,500 to $20,000

Rental ID 116456

  • RTR Vacation Rental
  • Lease $3,500 to $20,000
  • Village Oak Bluffs
  • Bedrooms 6
  • Bathrooms 3

Centrally located six bedroom Victorian home offers panoramic views of Ocean Park and the Vineyard Sound. Large, open spaces throughout home, huge kitchen, great for families. Convenient to Circuit Avenue shops and restaurants, just a short walk to the public beach. Central air conditioning.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details