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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246 Newton Avenue

Oak Bluffs, MA246 Newton Avenue

Price$1,750,000

Est. Mortgage: $/month

MLS ID 36905

  • Residential
  • Square Feet 1408
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 0.2899

Four bedroom family home OVERLOOKING and FRONTING Lagoon Pond. Commanding views up and down the Pond, across to VH harbor, Vineyard Sound & beyond to Falmouth. A picture perfect setting with active views and outstanding sunsets. Plus your own DEEPWATER DOCK, extending 115ft for boating and swimming pleasure. The first floor of this residence has a dining area, galley kitchen, 2 bedrooms, bath & utility room. 2nd floor has two add'l bedrooms, bath, entry den & large, open living room with sliders to a spacious deck. The grounds and embankment are lush green providing privacy yet yielding to the vast view. 2 car garage to rear with lots of storage space. This homes comes mostly furnished.

Listed by Towne & Country Realty

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$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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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4 Quail Run

Oak Bluffs, MA4 Quail Run

Price$585,000

Est. Mortgage: $/month

MLS ID 37276

  • Condominium
  • Village Sengy
  • Square Feet 1208
  • Bedrooms 2
  • Bathrooms 1

Located in beautiful Sengekontacket, offering access to Community Tennis, Clubhouse, and Boat Ramp. This two-bedroom townhouse is an end unit with a private deck. Many updates including wood floors on the first floor, new sliders, and windows on the side and rear. The bathrooms have been fully renovated with new tile floors, new vanities, and fixtures. The second floor fully renovated bathroom has new vanity, tub/shower with subway tile surround. New carpet in the bedrooms. Condominium dues for 2020 were $3,994. Sengekontacket Community dues are an additional $900. Community Fees include Association Tennis, Clubhouse, Water Access & Boat ramp. Condo Fees include Maintenance of common areas including the common decks, walkways, landscaping, parking, hazard insurance, and snow removal.

Listed by Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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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23 Hidden Cove Road

Oak Bluffs, MA23 Hidden Cove Road

Price$1,450,000

Est. Mortgage: $/month

MLS ID 37233

  • Residential
  • Village Sengy
  • Square Feet 2133
  • Bedrooms 3
  • Bathrooms 2

This well designed home in prestigious Hidden Cove flows beautifully from bright, open interior spaces to a private, lush yard. It is offered fully furnished and appointed, move-in ready to enjoy fall on the island. A huge wraparound deck and three season sunroom spill onto a bluestone patio, which overlooks a sweet lily pond. The custom kitchen is a chef's delight and has an amazing amount of storage space. The master suite comprises the whole second floor, with a cathedral ceiling, double closets and large bath with double vanities and a soaking tub. Adjacent to the master bedroom is a loft office offering plenty of space for remote working. There are two large bedrooms and a den on the lower level that share a luxurious bath, all overlooking the back yard. The association benefits include two tennis courts, pickleball, kayak and boat storage on Sengekontacket Pond, including a small dock. There are lovely walking trails in the neighborhood and it abuts acres of Felix Neck wildlife sanctuary.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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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One Cottage Park

Oak Bluffs, MAOne Cottage Park

Price$609,000

Est. Mortgage: $/month

MLS ID 37090

  • Residential
  • Square Feet 987
  • Bedrooms 3
  • Bathrooms 1
  • Half Bath 1

The epitome of vintage cottage charm! A short walk to beaches, ferries, harbor and Oak Bluffs town activities. From the first steps onto the perfect sitting porch and through scrolled double screened doors, this well-loved cottage is loaded with surprises and delights. Vintage windows and shutters intact, classic built-ins and a generous parlor set the welcoming tone. Unexpected front to back space offers comfortable seasonal living - first floor laundry room, pantry and updated bathrooms. Creative storage inside and low maintenance outside. Freshly painted and beautifully sited on a traffic free lane - You've found Gingerbread Cottage Perfection!

Listed by RE/MAX on Island

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$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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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38 Clinton Avenue

Oak Bluffs, MA38 Clinton Avenue

Price$649,000

Est. Mortgage: $/month

MLS ID 37158

  • Residential
  • Village Downtown
  • Square Feet 1447
  • Bedrooms 3
  • Bathrooms 2

Charming year round campground cottage. 3 bedrooms and 2 bathrooms with TWO parking spaces! This is an insulated 4 season home. Walk to beaches, town, restaurants, Tabernacle and everything Oak Bluffs has to offer. Fantastic location on corner lot, wonderful covered porch with historic detail, and a small shed for storage. The home has a first floor bedroom and bathroom, in addition to two upstairs bedrooms and bath; it also has an additional loft space at the top of stairs. Great year-round or vacation home at the right price!

Listed by Martha's Vineyard Island-Wide Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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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6 Laurel Avenue

Oak Bluffs, MA6 Laurel Avenue

Price$899,900

Est. Mortgage: $/month

MLS ID 37191

  • Residential
  • Village East Chop
  • Square Feet 755
  • Bedrooms 1
  • Bathrooms 1

COASTAL CONTEMPORARY CUSTOM DESIGN! Built in 2013 this 1 bedroom 1.5 bathroom home features a bright open living/kitchen/dining area on the first floor. The second floor has a spacious en suite master and cozy exterior balcony. Located less than 1/10th of a mile away from Oak Bluffs harbor, ferries, beaches and downtown shopping this home is a must see! FEATURES include Antique Nail Grade Hard Southern Yellow Pine from 300 year old beams in a Cataumet Saw Mill, Quartz counters in kitchen and bath White shaker cabinets in kitchen. Closed Cell Spray Foam Insulation & Ceilings on first floor have sound board insulation. A series and 400 Anderson doors and windows Interior trim is Harborside Molding! MUST SEE to APPRECIATE THE FINE CRAFTSMANSHIP!

Listed by Ocean Park Realty Inc

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$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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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11 Lawrence Avenue

Oak Bluffs, MA11 Lawrence Avenue

Price$719,000

Est. Mortgage: $/month

MLS ID 37035

  • Multi-Family
  • Bedrooms 3
  • Bathrooms 2

Walk to town Oak Bluffs from this unique two-family home. The main level offers an open floor plan with inviting farmer's porch to enjoy your morning coffee. A spacious kitchen is open to the living area. The light-filled bedroom with cathedral ceilings has sliding glass doors which lead out to the back deck and the small private, fenced-in “courtyard”. The second bedroom resides in the charming, detached “cottage”. Dine al fresco on the back deck or just relax with family and friends. The inviting outdoor shower is tucked on one end of the courtyard for maximum privacy and enjoyment. An exterior stairway on the side of the property brings you up to the second floor and entrance to the “Treetop apartment” which is a fully independent, cozy one-bedroom, one bath apartment with small private deck for relaxing. There is a drop-down ladder in the living room to access to the spacious attic; great for storage or awaiting someone's imagination. New Title V septic system installed in 2019 Located in a quiet, established neighborhood and walking distance to all the excitement that is downtown Oak Bluffs. Enjoy the Harbor, shops, restaurants, Ocean Park, Gingerbread Cottages and wonderful beaches just a short stroll away. A wonderful property with a multitude of uses. Come take a look.

Listed by Martha's Vineyard Island-Wide Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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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67 Dukes County Avenue

MLS ID 37117

  • Land
  • Village Downtown
  • Acreage 0.12

IN-TOWN OPPORTUNITY for a home and/or business just waiting for the right investor. Walk to the Harbor, Circuit Ave, the Tabernacle and Beaches. Currently there is a 4 bedroom "home" on the property. Potential to hook up to town sewer based on capacity. Property is sold "As-Is." Sellers do not make any representations or provide warranties regarding the potential use of the property. Buyers are responsible to perform their own due diligence.

Listed by Martha's Vineyard Seacoast Properties

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$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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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67 Dukes County Avenue

MLS ID 37116

  • Commercial
  • Village Downtown
  • Bedrooms 4

IN-TOWN OPPORTUNITY for a home and/or business just waiting for the right investor. Walk to the Harbor, Circuit Ave, the Tabernacle and Beaches. Currently there is a 4 bedroom "home" on the property. Potential to hook up to town sewer based on capacity. Property is sold "As-Is." Sellers do not make any representations or provide warranties regarding the potential use of the property. Buyers are responsible to perform their own due diligence.

Listed by Norbury, Alysha of Martha's Vineyard Seacoast Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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

67 Dukes County Avenue

MLS ID 37112

  • Residential
  • Village Downtown
  • Square Feet 974
  • Bedrooms 4
  • Acreage 0.12

IN-TOWN OPPORTUNITY for a home and/or business just waiting for the right investor. Walk to the Harbor, Circuit Ave, the Tabernacle and Beaches. Currently there is a 4 bedroom "home" on the property. Potential to hook up to town sewer based on capacity. Property is sold "As-Is." Sellers do not make any representations or provide warranties regarding the potential use of the property. Buyers are responsible to perform their own due diligence.

Listed by Martha's Vineyard Seacoast Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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

7 Old Harbor Lane

Oak Bluffs, MA7 Old Harbor Lane

Price$1,850,000

Est. Mortgage: $/month

MLS ID 37152

  • Residential
  • Village Sengy
  • Bedrooms 4
  • Bathrooms 2
  • Half Bath 1

Ocean Views and Neighborhood Beach access! This wonderful summer vacation retreat offers amazing view of Sengy Pond, State Beach, Nantucket Sound, & natural preserve open space. This home boasts inviting, spacious, vaulted ceilings, light and bright bedrooms that each look to the water. Take this house and turn it into your dream home! Bask in the rising sun from one deck and the setting sun from the other deck! This parcel adjoins conservation land offering peace and quiet while just an easy drive to the airport or two ferries. Waterview Farms is centrally located between three towns; Oak Bluffs, Vineyard Haven & Edgartown yet still very private being an exclusive community adjacent to Farm Neck Golf Course. This neighborhood provides beach access with boat storage and docking available. This spacious parcel is great for events & parties, or flying kites & out door games. Explore quaint nearby walking trails to Pecoy Point, or use your paddle board or kayak to enjoy Felix Neck & State beach! The MV biking trails access is at entrance to the community with an easy ride to town! Two adjoining build-able lots may be available for purchase, please inquire. Inquire about owner financing Please do not attempt to gain access to the house without being approved by listing agent. Additional photos of interior available upon request, houses are being rented. Thanks!

Listed by Sierra Properties & Investments

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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

18 Old Harbor Lane

Oak Bluffs, MA18 Old Harbor Lane

Price$889,000

Est. Mortgage: $/month

MLS ID 37142

  • Residential
  • Village Sengy
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 0.46

Nestled in the quiet neighborhood of Waterview Farms, this inviting home is the ideal location with pleasant meadow views and an opportunity to remodel a home to your specifications. This location is close to the bike path, tennis courts, and relished for its inviting feel and wonderful water experiences. You can enjoy boating and kayaking on Sengekontacket Pond, private access to the Waterview Farms beach and the association dock, boat storage and launch. This quaint home is light and bright with so much potential. A master bedroom with 3/4 shower, secondary bedroom and loft provide ample sleeping space. There is even a loft play area or reading nook! Come and envision what you would do with this wonderful location! Please note: this house is currently rented. Please do not attempt to gain access to the house without being approved by listing agent.

Listed by Sierra Properties & Investments

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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