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! Save your favorites when you register with us, and we can send you email updates when similar properties are posted. If you already have an account with us, log in here. Please feel free to contact us with any questions, for more information, or to schedule a showing for any property below!

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.

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

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Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Jun 22, 2017
* 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 2,200

Rental ID 135213

  • RTR Vacation Rental
  • Lease $1,600 to $2,200
  • Village Oak Bluffs
  • Bedrooms 2
  • Bathrooms 1

Completely renovated and updated 2 bedroom and 1 bathroom ranch home located in a quit neighborhood. The home is within walking distance to downtown Oak Bluffs, Circuit Ave, Ferry and Town beach

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Jun 22, 2017
* 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 and a 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.

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Jun 22, 2017
* 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 1,800

Rental ID 132907

  • RTR Vacation Rental
  • Lease $1,500 to $1,800
  • Village Oak Bluffs
  • Bedrooms 2
  • Bathrooms 1

This is a cozy Vineyard style perfect for a small family looking for a cute vacation home with lots of yard space for games and grilling. Downtown and Circuit Ave are minutes away on foot. Room a/c units, laundry, and more in this comfortable and charming home.

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Jun 22, 2017
* 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 132352

  • RTR Vacation Rental
  • Lease $4,000 to $5,500
  • Village Oak Bluffs
  • Bedrooms 3
  • Bathrooms 2

Tucked behind the trees this charming 10 sided home is a perfect getaway spot for families. A reverse set up, there are two bedrooms on the first floor, then the expansive living area is on the second with a deck encircling the front half of the house where water views are available. From up top you will enjoy the small deck offering stunning views of the sound, and a perfect retreat after a day of fun in the sun. Nearby East Chop Lighthouse, this is a terrific area from walking, jogging, or just enjoying East Chop at its best.

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Jun 22, 2017
* 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.

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Jun 22, 2017
* 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 5,000

Rental ID 132307

  • RTR Vacation Rental
  • Lease $4,000 to $5,000
  • 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.

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Jun 22, 2017
* 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$6,500 to 8,470

Rental ID 127428

  • RTR Vacation Rental
  • Lease $6,500 to $8,470
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 2

The Pratt House is what downtown Oak Bluffs is all about. Vintage charm and ocean views. Located on Waban park with views of the Inkwell. This five bedroom, 2 bathroom home is perfect for your next visit to the Vineyard!

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Jun 22, 2017
* 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

Rental Price$1,400 to 1,500

Rental ID 127278

  • RTR Vacation Rental
  • Lease $1,400 to $1,500
  • Village Oak Bluffs
  • Bedrooms 2
  • Bathrooms 1

New to the rental market this fall! this Charming two bedroom, two story home nestled within a beautifully landscaped English garden. We can not wait to see it all in bloom in the spring. You will feel like Hansel and Gretel on vacation!

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Jun 22, 2017
* 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

Rental Price$4,000 to 5,000

Rental ID 121877

  • RTR Vacation Rental
  • Lease $4,000 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.

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.90% last updated on Jun 22, 2017
* 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