Oak Bluffs Rentals

OAK BLUFFS is the island’s original summer resort, dating back to the late Victorian era. Its hallmarks include the colorful “gingerbread” aesthetic of its in-town neighborhoods, notably the historic Campground, where porch rocking and people watching are de rigeur. The young and young at heart revel in the lively scene of Circuit Avenue and the harbor front, day and night, while the outlying neighborhoods are a contrast in serenity. Town beaches front the calm and family-friendly waters of Nantucket Sound.

Learn more about Oak Bluffs.

Oak Bluffs real estate subareas:

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Rental Price$1,800 to $2,800

Rental ID 130923

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

“This vintage cottage in the heart of East Chop has been beautifully restored to bring modern amenities while retaining the old Vineyard charm. With beautifully restored floors, and whimsical coloring throughout this home, your family will enjoy this hidden gem for the perfect summer getaway. “

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Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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$4,140 to $7,500

Rental ID 130382

  • RTR Vacation Rental
  • Lease $4,140 to $7,500
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 3

This home walking distance to downtown Oak Bluffs has been lovingly restored. With five bedrooms and three and half baths and three floors of living space this home is big enough for the whole family. The king sized master is the entire second floor and has an en-suite bath and private deck. The first floor has four bedrooms with 2 shared baths. In the living room, kitchen and dining area you will enjoy open living concept with a beautiful brick fireplace as the centerpiece. The basement is finished beautifully with a 50 inch flat screen. Perfect for rainy day games.

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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$4,500 to $7,000

Rental ID 130298

  • RTR Vacation Rental
  • Lease $4,500 to $7,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 3

Gray s Oak offers in town living with ocean views out of every window and a beautiful front porch to watch the world go by on. The living room opens out on to the covered front porch for extended living space and warm ocean breezes. The king sized master with en-suite bath has its own private deck and fireplace.

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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$1,800 to $2,600

Rental ID 127339

  • RTR Vacation Rental
  • Lease $1,800 to $2,600
  • Village Oak Bluffs
  • Bedrooms 2
  • Bathrooms 1

Charming two bedroom home located in the heart of East Chop. Tastefully decorated one floor layout with a large family room on the lower level. Relax in the private backyard on the lovely deck area or stroll down the street to the East Chop Lighthouse with views of Vineyard Sound. Just a 15 minute walk to Circuit Avenue and beaches.

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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 $8,200

Rental ID 127105

  • RTR Vacation Rental
  • Lease $3,500 to $8,200
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 3

Beautifully appointed brand new four bedroom home. Steps to Niantic park, walk to Inkwell and downtown Oak Bluffs. Central air-conditioning and a lovely farmers porch to sit and watch the world go by.

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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$1,800 to $2,500

Rental ID 126491

  • RTR Vacation Rental
  • Lease $1,800 to $2,500
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 1

Cozy cottage in the right location with a porch and terrace. This home may just fit the bill with 4 bedrooms and 1.5 bathrooms along with an outside shower. A privet hedge affords privacy and there is a sweet playhouse at the end of the yard. Very compact, this home has nice gathering spaces though, along with good available parking for 3 or 4 cars. Suitable for some family bonding time. Dining room, little bar area off of kitchen and leading to the terrace. 2 small living rooms to relax in and catch up on people’s thoughts and day’s Vineyard activities. Bike to the Library via Pacific Ave or walk to the Arts District, restaurants and the fabled Tony’s market for sundries or Smoke n’ Bones (3 blocks) and beyond to the Campground Gingerbread Cottages, goings-on at the Tabernacle or the buzz of Circuit Ave.

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$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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 $6,750

Rental ID 126210

  • RTR Vacation Rental
  • Lease $4,000 to $6,750
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 3

Enjoy glorious sunrises and waterfront vistas from the expansive L-shaped open front porch. Claim a rocking chair and check out the goings on at the beach right across the street or see what’s up out on Nantucket Sound. This home is ship shape and hits just the right notes for a wonderful summertime vacation reunion of friends or family. New touches to this true Oak Bluffs Cottage include the traditional painted floor and fresh and cheery color coordinated decor in the bedrooms and sitting rooms.

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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 $4,000

Rental ID 125185

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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$4,400 to $5,000

Rental ID 122563

  • RTR Vacation Rental
  • Lease $4,400 to $5,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 3

View of Sunset Lake and distant views of Oak Bluffs harbor are at this 4 bedroom, 3.5 bath home. The first floor has a great, living, dining and kitchen area and den which offer a private staircase to the “Honeymoon” suite with private bath. Back in the living room you can enter a separate staircase which goes to second floor with 3 bedrooms. One with private bath, and distant water view and other bedroom sits in the back with shared bath with another front bedroom, also with distant water view. This home, with private driveway up to 4 cars also has a great front yard, front porch and outdoor shower. You are just a few blocks away from in town Oak Bluffs and all it shops & restaurants.

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$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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 $5,000

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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$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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$3,300 to $4,600

Rental ID 121539

  • RTR Vacation Rental
  • Lease $3,300 to $4,600
  • Village Oak Bluffs
  • Bedrooms 3
  • Bathrooms 2

This waterfront three bedroom two bath cottage offers spectacular views. Lounge on the lawn, watch the ferries come and go, and then the spectacular sunsets to follow.

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$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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 $2,500

Rental ID 121373

  • RTR Vacation Rental
  • Lease $1,500 to $2,500
  • 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.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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