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:

Please contact Coldwell Banker Landmarks Real Estate online or call 508-693-6866 with any questions about Martha’s Vineyard vacation rentals.

Rental Price$1,500 to $1,900

Rental ID 116748

  • RTR Vacation Rental
  • Lease $1,500 to $1,900
  • 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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Federal 30-year interest rate: 4.75% last updated on Dec 6, 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$5,900 to $8,100

Rental ID 116978

  • RTR Vacation Rental
  • Lease $5,900 to $8,100
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2

The Cinderella Cottage, a four bedroom Victorian home located in desirable Ocean Park is the perfect summer dream. Great location to downtown Oak Bluffs for shopping, restaurants, galleries and the ferry. Just two blocks from Inkwell beach and a short drive to State Beach. This vacation home has it all, charm and location.

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$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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$2,800 to $4,200

Rental ID 139295

  • RTR Vacation Rental
  • Lease $2,800 to $4,200
  • Village Oak Bluffs
  • Bedrooms 3
  • Bathrooms 2

Brand new spacious 3 bedroom, 2.5 bathroom home within a mile from Oak Bluffs Center and beach area. Every one will enjoy an attractive wraparound porch and comfortable screened in porch on a rainy day. This home has been tastefully furnished throughout and certainly would make you feel right at home on your Vineyard vacation.

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$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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 $7,500

Rental ID 116772

  • RTR Vacation Rental
  • Lease $3,500 to $7,500
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2

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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Federal 30-year interest rate: 4.75% last updated on Dec 6, 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$2,000 to $4,400

Rental ID 116856

  • RTR Vacation Rental
  • Lease $2,000 to $4,400
  • Village Oak Bluffs
  • Bedrooms 3
  • Bathrooms 2

Quaint family cottage on Vineyard Haven outer harbor with great ocean views. Private beach, dock and mooring. Adequate parking, including area for a boat trailer. Beautiful sunsets, ideal for a family vacation.

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%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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 $10,000

Rental ID 114888

  • RTR Vacation Rental
  • Lease $4,500 to $10,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 1

Victorian four bedroom farmhouse style home located on Waban Park in Oak Bluffs. Walking distance to beaches and town. Quiet neighborhood.

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Federal 30-year interest rate: 4.75% last updated on Dec 6, 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 $4,000

Rental ID 114883

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

Two story expanded cape style home, completely renovated. Tastefully decorated and comfortably furnished throughout. Includes an outdoor deck off of dining room great - for relaxing and dining outdoors. Enclosed outdoor shower. Waterview of Lagoon from side of house.

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$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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 $9,000

Rental ID 114965

  • RTR Vacation Rental
  • Lease $4,000 to $9,000
  • Village Oak Bluffs
  • Bedrooms 6
  • Bathrooms 4

Beautiful Vineyard home overlooking the ocean on Farm Neck Golf Course. Five bedroom, four baths, open living area with screened in porch, large wrap-around deck. Also small guest apartment over the garage with one bedroom, bath and living room. Tennis and golf on the grounds, public beach nearby. Private lawn and gardens, spectacular tree house.

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%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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$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.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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$1,300 to $1,950

Rental ID 116503

  • RTR Vacation Rental
  • Lease $1,300 to $1,950
  • Village Oak Bluffs
  • Bedrooms 2
  • Bathrooms 1

The Blue Canoe is a bright, welcoming vintage 1900 s cottage with enormous charm and style. Freshly renovated, and decorated with an eye to capturing the casual and colorful feel of an island retreat. Ideally located on a quiet street, within walking distance of the village, the beach and parks. A nice fenced-in side yard with large deck and outdoor furniture to relax and dine. A great getaway for year-round enjoyment, conveniently located with all the comforts you ll need for the perfect vacation.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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$6,000 to $9,000

Rental ID 137764

  • RTR Vacation Rental
  • Lease $6,000 to $9,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 4

Enjoy the perfect vacation in this updated gingerbread house, that offers gorgeous view from every angle. The home offers 4 en-suite bedrooms and plenty space for entrainment.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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 $5,500

Rental ID 135243

  • RTR Vacation Rental
  • Lease $3,300 to $5,500
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 5

Bright, open totally redesigned, restored and expanded summer cottage on a quiet street in an historic and lovely neighborhood. Less than 1/2 mile from town. Open space plan for maximum interaction for everyday or special gatherings. Private nooks for book reading. Numerous large windows throughout home for a light, airy feeling. Beautiful hardwood floors and ceramic tiles throughout. Top of the line appliances and granite countertops in the kitchen. Many extras. First floor master suite and laundry. Ceiling fans in each bedroom as well as central a/c. A newly finished basement with large flat screen TV, ping pong table, and an extra 1/2 bath to spread out and relax. Rocking chairs on wrap around porch.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 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