Oak Bluffs Vacation Rentals

Discover our latest vacation rentals in the Martha's Vineyard town of Oak Bluffs. Look through a variety of listings including beautiful oceanfront homes, luxury estates, cottages, and more! Save your favorites when you register with us, and we can send you email updates when similar properties are posted. If you already have an account with us, log in here. Please feel free to contact us with any questions, for more information, or to schedule a showing for any property below!

Rental Price$2,500 to $4,500

Rental ID 133793

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

This well appointed home centrally located is only 1.5 miles to downtown Oak Bluffs. The 4 BEDROOMS 2.5 BATHS house is in an established & desirable community with association tennis courts. Plenty of space for the whole family to spread out with both a more formal sitting room for reading and conversation and television room just off the kitchen. On the second floor; master bedroom with en suite bath allows for privacy and three more bedrooms share a bathroom on the second floor. Lovely deck for grilling and dining al fresco!

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Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

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Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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$4,000 to $9,000

Rental ID 114965

  • RTR Vacation Rental
  • Lease $4,000 to $9,000
  • Village Oak Bluffs
  • Bedrooms 6
  • Bathrooms 4

Beautiful Vineyard home overlooking the ocean on Farm Neck Golf Course. Five bedroom, four baths, open living area with screened in porch, large wrap-around deck. Also small guest apartment over the garage with one bedroom, bath and living room. Tennis and golf on the grounds, public beach nearby. Private lawn and gardens, spectacular tree house.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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$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.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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$1,300 to $1,950

Rental ID 116503

  • RTR Vacation Rental
  • Lease $1,300 to $1,950
  • Village Oak Bluffs
  • Bedrooms 2
  • Bathrooms 1

The Blue Canoe is a bright, welcoming vintage 1900 s cottage with enormous charm and style. Freshly renovated, and decorated with an eye to capturing the casual and colorful feel of an island retreat. Ideally located on a quiet street, within walking distance of the village, the beach and parks. A nice fenced-in side yard with large deck and outdoor furniture to relax and dine. A great getaway for year-round enjoyment, conveniently located with all the comforts you ll need for the perfect vacation.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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$1,800 to $2,600

Rental ID 127339

  • RTR Vacation Rental
  • Lease $1,800 to $2,600
  • Village Oak Bluffs
  • Bedrooms 2
  • Bathrooms 1

Charming two bedroom home located in the heart of East Chop. Tastefully decorated one floor layout with a large family room on the lower level. Relax in the private backyard on the lovely deck area or stroll down the street to the East Chop Lighthouse with views of Vineyard Sound. Just a 15 minute walk to Circuit Avenue and beaches.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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

Rental Price$3,000 to $5,005

Rental ID 135246

  • RTR Vacation Rental
  • Lease $3,000 to $5,005
  • Village Oak Bluffs
  • Bedrooms 3

Spacious, air conditioned 3BR home in private Sengekontacket Association with benefits of community docks, tennis courts and walking trails. Open and awash with natural light, pine flooring, delightful wood trim and beamed ceilings. Master suite and loft/study on 2nd floor has jetted tub, soaring ceilings and skylights. Fully equipped kitchen with granite counters, center island with additional bar seating, gas range and stainless appliances flows to dining room and inviting living room. Guest powder room adjacent to entry foyer. Sliding doors lead to upper deck with retractable awning. Finished lower level has 2 bedrooms each with sliding doors leading to lower deck. A shared full bathroom, game space, laundry room and unique curved outdoor shower also on lower level. Close to town and beaches - located on bike path and bus route.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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

Rental Price$4,000 to $6,750

Rental ID 126210

  • RTR Vacation Rental
  • Lease $4,000 to $6,750
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 3

Enjoy glorious sunrises and waterfront vistas from the expansive L-shaped open front porch. Claim a rocking chair and check out the goings on at the beach right across the street or see what’s up out on Nantucket Sound. This home is ship shape and hits just the right notes for a wonderful summertime vacation reunion of friends or family. New touches to this true Oak Bluffs Cottage include the traditional painted floor and fresh and cheery color coordinated decor in the bedrooms and sitting rooms.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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

Rental Price$3,000 to $3,200

Rental ID 116762

  • RTR Vacation Rental
  • Lease $3,000 to $3,200
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2

This charming, recently renovated waterfront two-story cape situated atop the lagoon bluffs boasts spectacular sunsets and panoramic views of Lagoon, outer Vineyard Haven harbor and Cape Cod from the patios, living room, dining room and two upstairs bedrooms. Stairs down to private beach.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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

Rental Price$1,900 to $2,550

Rental ID 116387

  • RTR Vacation Rental
  • Lease $1,900 to $2,550
  • Village Oak Bluffs
  • Bedrooms 3
  • Bathrooms 2

Bright, spacious home located in a quiet neighborhood. Approx 0.5 mile from Oak Bluffs down town area. Walk or ride out of driveway directly onto the bike path. Professionally decorated throughout. Open space plan for maximum enjoyment. Large dining room for everyday or special gatherings. Abundant large windows throughout home for a light/airy feeling. Stone fireplace (gas powered) in the great room. Beautiful hardwood floors throughout living level. Master suite includes large private bathroom with ceramic floors and granite countertop. Ceiling fans in each bedroom as well as central air. The perfect home away from home.

{$agent->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* 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