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$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.

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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: 4.03% last updated on Jul 13, 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$5,000 to 5,500

Rental ID 134166

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

Brand New to the Rental Market for 2017! This four bedroom, two and a half bath home located in the heart East Chop is newly renovated. Beautiful kitchen, dining living space with french doors that lead to a large screened in porch for dining al fresco. Family room on the ground level for the kids to play and watch television. Four bedrooms, including master with newly renovated master bath. All of this and central air conditioning throughout!

{$agent->Name}

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: 4.03% last updated on Jul 13, 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$5,000 to 7,000

Rental ID 133995

  • RTR Vacation Rental
  • Lease $5,000 to $7,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 3

This brand new construction located just minutes from downtown Oak Bluffs is well appointed and comfortable. A first floor master outfitted with a king bed and is ADA compliant is perfect for grandparents or the nanny. Upstairs you will find three more bedrooms. A generous sized master with sitting area and en suite bath. Two additional bedrooms that share a lovely bath with double vanity and walk in shower. The living area is open concept with a 65 inch flat screen television and comfortable furnishings for movie night. The kitchen is well appointed with high end pots and pans as well as a kitchen-Aid mixer.

{$agent->Name}

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: 4.03% last updated on Jul 13, 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$1,500 to 3,000

Rental ID 132907

  • RTR Vacation Rental
  • Lease $1,500 to $3,000
  • 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.

{$agent->Name}

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: 4.03% last updated on Jul 13, 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 5,500

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.

{$agent->Name}

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: 4.03% last updated on Jul 13, 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$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.

{$agent->Name}

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: 4.03% last updated on Jul 13, 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 5,500

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.

{$agent->Name}

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: 4.03% last updated on Jul 13, 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$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!

{$agent->Name}

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: 4.03% last updated on Jul 13, 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$7,500 to 7,500

Rental ID 126949

  • RTR Vacation Rental
  • Lease $7,500 to $7,500
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2

Charming four bedroom Greek Revival farmhouse located on East Chop. Impeccably maintained home and yard, relax and enjoy the large wrap around farmers porch. Well appointed, comfortably furnished interior with fully equipped kitchen including a dual/Viking range and wall oven. Ideal open living area perfect for entertaining and enjoying family time. Master bedroom opens onto a screened in porch with rocking chairs. There is also a separate family room with ping pong table. Conveniently located to town, just a short walk to East Chop Lighthouse.

{$agent->Name}

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: 4.03% last updated on Jul 13, 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$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.

{$agent->Name}

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: 4.03% last updated on Jul 13, 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