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$6,000 to $11,000

Rental ID 137764

  • RTR Vacation Rental
  • Lease $6,000 to $11,000
  • 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.

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Federal 30-year interest rate: 3.18% last updated on Jun 4, 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 $6,000

Rental ID 135243

  • RTR Vacation Rental
  • Lease $3,300 to $6,000
  • 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: 3.18% last updated on Jun 4, 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$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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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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$3,500 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: 3.18% last updated on Jun 4, 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: 3.18% last updated on Jun 4, 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 $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.

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$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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 TourAsk A QuestionMore Details

Oak Bluffs, MA

Rental Price$5,250 to $15,750

Rental ID 141578

  • RTR Vacation Rental
  • Lease $5,250 to $15,750
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 3

Endless views of the ocean, directly across from the water, and steps away from a sandy beach excellent for swimming. Gorgeously remodeled last summer (2018) and designed with a sophisticated California-meets-MV feel inside, our welcoming, centrally-air-conditioned, 4 bedroom house sleeps 10 and is a rarity in this area. Blonde wood wide plank flooring, new kitchen, new doors & windows, mattresses, and appliances including dishwasher, gas range, French door refrigerator with ice maker and a king size bed in a larger than usual (for OB) master BR. The house is airy and uncluttered, with a wide 3-sided wraparound porch, perfect for watching the annual fireworks, dining outside or watching the world go by. 4 well appointed bedrooms -- one downstairs and three upstairs (including a larger bedroom with a queen & 2 twins which is perfect for sharing). Second-story deck off the master bedroom offers views of the ocean, as well as Farm Pond. A second porch off the second & third upstairs bedrooms also has ocean views. Two sets of French doors from the kitchen and dining area open out to a larger portion of the deck and stunning ocean views. Updated bathrooms (glass-door subway tile walk-in shower downstairs, a deep soaking tub upstairs), wide porches to relax and dine on, and an open and connected feeling downstairs (a wood topped bar/island connects guests to the dining area and the kitchen, open french doors connect it all to the deck and the outdoor seating/dining). The house is set back from the road by a generous lawn, and is a very short distance (a few houses) to the bike path that runs along the island s edge & State Beach and into Edgartown, and within easy walking distance of both the Oak Bluffs ferry docking and the shops and restaurants in town and along the harbor, so you ll never have to search for a parking space to dine in-town in the high season. There s a large dining table inside & barbecue and additional outdoor seating/dining table on the porch, TV (televisions in the living room and the master BR). 1 king bed, 2 queen beds, 1 full sized bed, and 2 twin beds. Additionally, upon request/discussion, there is a back guest cottage aka "The Nest". The Nest has a good size upstairs bedroom (offering what is then a 5th BR); queen bed and a twin bed (sharing the same room), a deck off the bedroom that has water views (ocean and Farm Pond), The guest house is air conditioned with mini split.

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%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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 TourAsk A QuestionMore Details

Oak Bluffs, MA

Rental Price$6,000 to $14,000

Rental ID 139055

  • RTR Vacation Rental
  • Lease $6,000 to $14,000
  • 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.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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 TourAsk A QuestionMore Details

Oak Bluffs, MA

Rental Price$3,000 to $7,000

Rental ID 136204

  • RTR Vacation Rental
  • Lease $3,000 to $7,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2

Beautiful home in a perfect location in Oak Bluffs. Fully renovated in 2015 including central A/C and huge deck with pergola! This home is very well kept and lovingly furnished for both style and comfort with a spacious layout for vacations with families and friends. Large two-story, classic Cape Cod style home with 4 Bedrooms and 2 Full Baths, includes large deck, screened porch, outdoor stone patio and furnished basement. Located close enough to the action of Curcuit Avenue in downtown Oak Bluffs, yet tucked away in a quit neighborhood, with easy access to key routes along County and Barnes Roads, this home is secluded by the surrounding forests of the school yards and Trade Winds Field and Trails. The expansive first floor includes a newly remodeled, open-concept kitchen, which opens up to a large great room with dining room and sitting areas and a separate family room with 55 TV. French doors and sliders open up to several, large outdoor areas, including a deck, a screened porch and a stone patio. The doors also allow wonderful island breezes throughout the home. A private bedroom is also located on the first floor, along with a renovated full bathroom. Oak hardwood floors are featured throughout the entire interior of the home. The second floor has 3 bedrooms and a full bath. The basement is furnished as a game room and home theater with a 65 TV and real 10 shuffle board table, as well as DVDs, games, cards and more. Families with children can also enjoy the benefits of Oak Bluffs school playground and tennis courts located adjacent to the property as well. The many beautiful outdoor spaces of the home seem endless. They include a large deck covered with cedar pergola and outdoor dining

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%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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$3,000 to $6,000

Rental ID 135069

  • RTR Vacation Rental
  • Lease $3,000 to $6,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 1

Leave your worries and your car behind - this picture perfect Vineyard beach house is steps from downtown Oak Bluffs, the sandy beach and a few short blocks from the ferry. Recently renovated and restored, four bedrooms and one full and two half baths, offering the perfect juxtaposition of cottage charm and modern beach chic; the style is incredibly livable, comfortable, colorful and relaxed - all vital ingredients to the perfect vacation.

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$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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 TourAsk A QuestionMore Details

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: 3.18% last updated on Jun 4, 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 TourAsk A QuestionMore Details

Oak Bluffs, MA

Rental Price$5,500 to $5,500

Rental ID 132307

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

We welcome you to enjoy our spacious and comfortable home. It s a beautiful 5 BR, 4.5 bath Oak Bluffs home with modern conveniences and nestled in an idyllic, secluded location. Perfect for large family gatherings. The amenities include AC, granite kitchen counter tops, breakfast bar, W/D, WiFi, five flat screen cable TVs, DVD & VHS players, gas grill, outdoor shower, hardwood floors and wood-burning fireplace for ambiance or a chilly evening. Large dining room table (comfortably seats 8) and fully equipped kitchen includes dishwasher and stock pots for steaming your crabs, clams & lobsters for that ultimate Vineyard experience. The house is located on a quiet street, has a private back yard and 2 large decks for casual dining and relaxing. Close to everything - town (5 minute drive/15 min walk) , harbor, ferry, shops, and restaurants.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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 TourAsk A QuestionMore Details