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! You may also be interested in browsing all of our vacation rentals.

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

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Rental Price$3,500 to $5,000

Rental ID 121877

  • RTR Vacation Rental
  • Lease $3,500 to $5,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 4

Colorful water view Victorian cottage with wrap around Mahogany porch, and west side brick way leading to a rear porch and blue stone patio. Beautifully landscaped with premiere privet shrubs and trees. The interior is wired for sound with speakers throughout. The well tooled kitchen has granite countertops and Eastern sunlight.

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Federal 30-year interest rate: 3.73% last updated on Sep 19, 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$5,500 to $8,000

Rental ID 121796

  • RTR Vacation Rental
  • Lease $5,500 to $8,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 4

This 4 bedroom, 4.5 bath is a Victorian gem near Ocean park. The front porch offers much relaxation on evening nights, and leads into first floor with living & dining room, great kitchen with patio off kitchen and a nice family room for movie watching on a rainy day. Also off the family room, is the driveway and another patio that leads to outdoor enclosed shower. The second floor has all 4 bedrooms each with their own private bath. This floor’s layout offers a great setup for families. The master bedroom is at the front of the house with private deck, great for early morning coffee enjoyment. This home is walking distance to town, park, ferry and even beach, a perfect Oak Bluffs vacation home!

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$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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$1,500 to $2,675

Rental ID 121373

  • RTR Vacation Rental
  • Lease $1,500 to $2,675
  • Village Oak Bluffs
  • Bedrooms 3
  • Bathrooms 2

Sunny contemporary, newly furnished home located in a beautifully landscaped association. Providing tennis courts and a kayak landing on Sengenkentac. With a screened in porch and deck there is plenty of space for outdoor living. Centrally located only a short drive to downtown Oak Bluffs, Edgartown, Vineyard Haven and down island beaches.

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$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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 $5,400

Rental ID 119948

  • RTR Vacation Rental
  • Lease $3,500 to $5,400
  • 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: 3.73% last updated on Sep 19, 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$2,900 to $5,500

Rental ID 118274

  • RTR Vacation Rental
  • Lease $2,900 to $5,500
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 2

This five bedroom in-town Oak Bluffs home offers the perfect location to walk to town and beach. The living room opens out to the front wrap around porch which is great for people watching and family dinners. The first floor bedroom makes it easy for some family members and then upstairs includes four bedrooms that share a bathroom. The master bedroom looks out to street and distant ocean waterview from porch. Bring your coffee and newspaper and enjoy.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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$2,000 to $3,500

Rental ID 116945

  • RTR Vacation Rental
  • Lease $2,000 to $3,500
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 3

Located in serene Iron Hill Farm, this spacious contemporary Cape offers large rooms, extensive outdoor living space with multiple decks, beautiful gardens and a basketball hoop on the property s two acres. A large master suite located on the first floor offers a california king, full bath and private deck. A bonus sunroom on the first floor doubles as a playroom for kids or a bar with a refrigerator and sink for adults. Centrally located, and only minutes from the townships and beautiful beaches of Edgartown, Oak Bluffs and Vineyard Haven.

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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$1,600 to $2,300

Rental ID 116938

  • RTR Vacation Rental
  • Lease $1,600 to $2,300
  • Village Oak Bluffs
  • Bedrooms 2
  • Bathrooms 2

Great Vineyard location on Vineyard Avenue in Oak Bluffs. Built in 1920 and thoughtfully restored in 1999, this house is clean, neat and conveniently located a few hundred feet from the the Oak Bluffs Arts District. Within walking distance through the Campground (gingerbread cottages) to shops, restaurants, Flying Horses and the Oak Bluffs waterfront. Just a fifteen minute walk to East Chop beach and the ferry. Enjoy the outdoors on the covered farmers porch overlooking the herb garden in front or the semi-private deck in back. Detached bunkhouse in back yard is a great playhouse for kids or for storing bikes.

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$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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: 3.73% last updated on Sep 19, 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: 3.73% last updated on Sep 19, 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 116748

  • RTR Vacation Rental
  • Village Oak Bluffs
  • Bedrooms 1
  • Bathrooms 1

This charming guest house is steps from town and harbor. New and contemporary interior furnishings with attractive landscaping and common outside shower.

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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