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.

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Rental Price$4,000 to $8,750

Rental ID 139449

  • RTR Vacation Rental
  • Lease $4,000 to $8,750
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2

Begin and end your Vineyard vacation search with this amazing home. If you are fit enough to climb a flight of stairs, it absolutely will not disappoint! Home boasts an upside-down design, specifically laid out to capture incredible WATER VIEWS from almost every room. It boasts 4 bedrooms (king, queen, queen, and two twins able to be kinged). Home also has two spacious living areas, many decks, both covered and uncovered, a four-person HOT TUB, and nice extras: use of beach chairs, beach towels, and brand new furnishings. Upscale appliances complete this open concept kitchen. Your only disappointment will be when you need to leave. Although this home is BRAND NEW to the rental market, we have been renting homes in Oak Bluffs for many years. We also build and sell them, and are experienced in providing vacationers with a wonderful experience. Walk to Eastville Beach and the Landbank Lagoon Beach (less than 1/8 mile), and bike to Vineyard Haven and Oak Bluffs from your vacation home. Or, if you prefer, step outside your door and hop on the Vineyard Transit Bus to anywhere....Farm Neck Golf, Aquinnah Cliffs and South Beach! Just bring your bathing suit and prepare to relax and enjoy!

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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$2,650 to $3,800

Rental ID 114932

  • RTR Vacation Rental
  • Lease $2,650 to $3,800
  • Village Oak Bluffs
  • Bedrooms 3
  • Bathrooms 3

Spacious three bedroom, three and half bath home, only one mile from downtown Oak Bluffs. Bright, airy comfortably furnished interior with hardwood floors throughout. Open living and dining area with fully equipped kitchen. Nice yard with outdoor deck for entertaining or relaxing after a day on the Vineyard.

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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 $4,500

Rental ID 139152

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

The light filled and very spacious 2 + bedroom home has just been renovated and all newly furnished. Located in well known Waterview Farms community of Oak Bluffs, the house is in a private setting, but just a short drive to multiple public beaches and village center of Oak Bluffs, Edgartown and Vineyard Haven. Enjoy the spacious and plenty light filled inside or gorgeous well maintained outside on your perfect family getaway on Martha s Vineyard.

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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$9,500 to $9,500

Rental ID 116602

  • RTR Vacation Rental
  • Lease $9,500 to $9,500
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 4

Spectacular waterfront home on Sengekontacket Pond located in Farm Neck. Immaculate, open airy home with beautiful interior providing views of water on all three sides - Chappy, Edgartown and Farm Neck golf course. Private, shared Association dock & mooring as well as small beach. One minute drive to State Beach, ten minute walk to Farm Neck (pay to play golf and tennis). A great vacation getaway.

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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$3,300 to $6,500

Rental ID 116299

  • RTR Vacation Rental
  • Lease $3,300 to $6,500
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 2

Large Victorian, beautifully furnished in wicker and mahogany with stone fireplace and large stained-glass window. Includes a gourmet kitchen and formal dining room. Enjoy outdoor relaxation time on the wraparound porch and large fenced in yard. This magnificent five bedroom home is bright and airy with lovely wood flooring throughout. Fantastic location surrounded by Oak Bluffs picturesque Victorians, and an easy stroll to town or beach.

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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$3,000 to $4,000

Rental ID 125185

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

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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$3,400 to $3,400

Rental ID 116438

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

Walk to town, beach and ferry from this up-to-date home with traditional stylings, including a deep farmer s porch. Barbecue on the patio of this quiet, treed lot. Three roomy bedrooms, loads of charm, lots of amenities throughout and central A/C, too! NOTE: Homeowner will accept one additional infant.

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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$8,825 to $10,600

Rental ID 132137

  • RTR Vacation Rental
  • Lease $8,825 to $10,600
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2

Waterfront custom Farmhouse overlooking Crystal Lake toward East Chop Drive. There is a large manicured lawn and garden with a path to the lake and a row boat for your enjoyment. Sit on the expansive deck and use the 8 x15 hot tub/ dip pool, outdoor shower and enjoy the view, or grill on your brick patio (ALL WITH INCREDIBLE VIEWS). A very peaceful location, yet a five minute drive to Circuit Ave, East Chop Light, and the beaches of Oak Bluffs. Vineyard Haven and Oak Bluffs ferries are also a five minute drive. A great area for the kids to play and FAMILIES to get around very easily. Also lovely walking paths nearby for birdwatchers. This well-maintained, well-equipped house offers linens and towels, bicycles, and is loaded with amenities. The first floor offers a large modern kitchen, breakfast bar open to the dining room and a large living room all with views of a lovely yard, Crystal Lake, and Vineyard Sound oceanfront beyond. There is also a sun room, 2 bedrooms, and 1.5 baths on this floor.

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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$2,900 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: 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 ID 116942

  • RTR Vacation Rental
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 2
  • Half Baths 1

Classic Victorian beach house with four bedrooms and Guest studio/office. Waterviews from porch, master bedroom and upstairs balcony. Private, fenced seating area, flower-filled garden with large picnic table. Great wrap around porch with rocking chairs and beach view. Also on the property is a newly remodeled garden guest cottage which includes a separate kitchen, washer, dryer, bathroom with shower, futon full bed and a garden table and chair. A perfect in-law or nanny suite. This property also has space for two cars in front of house & cottage.

$
$
%
$/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 $6,000

Rental ID 136665

  • RTR Vacation Rental
  • Lease $3,500 to $6,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 3

Oak Bluffs is the front entry way. The Inkwell Beach is the living room with a large flat screen TV with surround a sound and a dining area, the kitchen area with an island cooking surface it is where all the action happens this flat screen today. . The family room downstairs is named Chilmark where you can play cards, games, or read your favorite book when you want to just “chill”, of course the kids can take over the room for their indoor activities. The bedroom on the main level is named West Tisbury with queen bed and access to the outdoor deck. A full bath is located next to the room with a bath and shower. On the second level you will find the master bedroom named Edgartown, it has king bed and a daybed for watching television or window gazing has an en suite bathroom that includes a shower and tub. Menemsha is the second bedroom and has a double bed next to a beautiful Jack and Jill bathroom with shower. . The Vineyard is the second master and has two queen beds and other exquisite decor.

$
$
%
$/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$1,500 to $4,000

Rental ID 121100

  • RTR Vacation Rental
  • Lease $1,500 to $4,000
  • Village Oak Bluffs
  • Bedrooms 2
  • Bathrooms 2

This well appointed larger corner unit faces the Inkwell Beach and historic Waban Park. Spacious living with two bedroom, and two baths. A short walk to Circuit Ave, and the Oak Bluffs Harbor.

$
$
%
$/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