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$1,500 to $3,750

Rental ID 132471

  • RTR Vacation Rental
  • Lease $1,500 to $3,750
  • Village Oak Bluffs
  • Bedrooms 2
  • Bathrooms 2

A peaceful retreat! Renovated cottage with modern furnishings on a large 1.99 acre landscaped lot in Fresh Pond Estates, an exclusive private community. The home is a two bedroom, two bath residence with a private sleeping den with a deluxe queen sleeper sofa allowing guests to convert into a three bedroom home. Convenient location off County Road Bike Path, equidistant to all Down Island Towns and a short bike ride to Farm Neck Golf & Tennis Club! This is a perfect rental for the active family. Beautiful Pastoral setting and a wonderful Screened Porch with plenty of seating for lounging and dining. There is a deck that wraps around the home with plenty of seating for outdoor dining or a family BBQ. A short drive to beaches and downtown shopping in Oak Bluffs, Vineyard Haven and Edgartown. Walking and biking trails are just steps away! The home is on a quiet, well-maintained private road and a perfect location for those seeking peace and quiet in a beautiful home!

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Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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$7,000 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: 3.5% last updated on Mar 26, 2020
* 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: 3.5% last updated on Mar 26, 2020
* 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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Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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: 3.5% last updated on Mar 26, 2020
* 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 133995

  • RTR Vacation Rental
  • Lease $5,500 to $8,000
  • 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.

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$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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: 3.5% last updated on Mar 26, 2020
* 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 135213

  • RTR Vacation Rental
  • Village Oak Bluffs
  • Bedrooms 2
  • Bathrooms 1

Completely renovated and updated 2 bedroom and 1 bathroom ranch home located in a quit neighborhood. The home is within walking distance to downtown Oak Bluffs, Circuit Ave, Ferry and Town beach

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$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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$4,000 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.

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$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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$2,500 to $6,500

Rental ID 144438

  • RTR Vacation Rental
  • Lease $2,500 to $6,500
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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 $4,400

Rental ID 139295

  • RTR Vacation Rental
  • Lease $3,500 to $4,400
  • 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: 3.5% last updated on Mar 26, 2020
* 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$4,700 to $7,070

Rental ID 130382

  • RTR Vacation Rental
  • Lease $4,700 to $7,070
  • 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.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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