Oak Bluffs Rentals

Vacation Rentals in Oak Bluffs, Martha's VineyardFind Martha’s Vineyard vacation rentals in Oak Bluffs, the island’s original summer resort and a very popular family vacation area. Its hallmarks include the colorful “gingerbread” houses 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. View available Oak Bluffs rentals below. You may also be interested in viewing all vacation rentals on the Vineyard.

Oak Bluffs real estate subareas:

Oak Bluffs Vacation Rentals

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Oak Bluffs, MA

Rental Price$7,000 to $145,000

Rental ID 126030

  • RTR Vacation Rental
  • Lease $7,000 to $145,000
  • 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.

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Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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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Oak Bluffs, MA

Rental Price$6,000 to $13,500

Rental ID 139055

  • RTR Vacation Rental
  • Lease $6,000 to $13,500
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 4

Luxury home located in a parkland setting in Sengekontacket - peaceful and serene yet close to downtown Oak Bluffs and the rest of the Vineyard. This new construction home has a large gourmet kitchen and wide open space adjacent dining and living areas. It is perfect layout for families to gather and socialize. The first floor opens onto a stone patio and grassy landscaped yard - ideal for grilling and outdoor entertaining. There is a large en-suite master bedroom on the first floor. Sliding doors open to a private back deck - perfect for enjoying your morning coffee. Four additional bedrooms are located on the second floor. Queen sized bedroom with private bath. Full sized bedroom with private bath. Two bedrooms with two twin beds give your family multiple sleeping arrangements. There is an association boat launch that is available for your kayaks.

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$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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 137764

  • RTR Vacation Rental
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 4
  • Half Baths 1

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.

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$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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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Oak Bluffs, MA

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.

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$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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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Oak Bluffs, MA

Rental Price$7,500 to $9,500

Rental ID 116602

  • RTR Vacation Rental
  • Lease $7,500 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: 3.68% last updated on Dec 5, 2019
* 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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Oak Bluffs, MA

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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Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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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Oak Bluffs, MA

Rental Price$2,000 to $3,900

Rental ID 116856

  • RTR Vacation Rental
  • Lease $2,000 to $3,900
  • 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: 3.68% last updated on Dec 5, 2019
* 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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Oak Bluffs, MA

Rental Price$4,400 to $5,300

Rental ID 122563

  • RTR Vacation Rental
  • Lease $4,400 to $5,300
  • 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: 3.68% last updated on Dec 5, 2019
* 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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Oak Bluffs, MA

Rental Price$5,500 to $8,000

Rental ID 121796

  • RTR Vacation Rental
  • Lease $5,500 to $8,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 4

This 4 bedroom, 4.5 bath is a Victorian gem near Ocean park. The front porch offers much relaxation on evening nights, and leads into first floor with living & dining room, great kitchen with patio off kitchen and a nice family room for movie watching on a rainy day. Also off the family room, is the driveway and another patio that leads to outdoor enclosed shower. The second floor has all 4 bedrooms each with their own private bath. This floor’s layout offers a great setup for families. The master bedroom is at the front of the house with private deck, great for early morning coffee enjoyment. This home is walking distance to town, park, ferry and even beach, a perfect Oak Bluffs vacation home!

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%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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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Oak Bluffs, MA

Rental Price$950 to $1,800

Rental ID 113594

  • RTR Vacation Rental
  • Lease $950 to $1,800
  • Village Oak Bluffs
  • Bedrooms 2
  • Bathrooms 1

This home is all about convenience. Cute two bedroom cottage within walking distance to the center of Oak Bluffs. The exterior of this home includes a wrap around deck, screened in porch, gardens, one car driveway and an outdoor shower with hot and cold water. The interior of the home is a bit older but is perfectly adequate for a great vacation home and is priced accordingly. The first floor offers an older full bathroom with a claw foot tub, older kitchen with good sized dining area, and a living room with pine floors, flat screen tv and dvd player. The second floor includes two bedrooms.

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$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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

Oak Bluffs, MA

Rental Price$3,500 to $4,900

Rental ID 138827

  • RTR Vacation Rental
  • Lease $3,500 to $4,900
  • Village Oak Bluffs
  • Bedrooms 3
  • Bathrooms 2

Classic Cape style home, Serenity at its best. Open kitchen/dining and living room that flows easily onto a beautiful slate patio. Master bedroom suite on first floor with two additional bedrooms. Finished lower level, fun room, media and games. Close access to boating and a lagoon beach. Newly furnished, awesome backyard and amenities.

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$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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

Oak Bluffs, MA

Rental Price$2,000 to $3,500

Rental ID 116945

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

Located in serene Iron Hill Farm, this spacious contemporary Cape offers large rooms, extensive outdoor living space with multiple decks, beautiful gardens and a basketball hoop on the property s two acres. A large master suite located on the first floor offers a california king, full bath and private deck. A bonus sunroom on the first floor doubles as a playroom for kids or a bar with a refrigerator and sink for adults. Centrally located, and only minutes from the townships and beautiful beaches of Edgartown, Oak Bluffs and Vineyard Haven.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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