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$4,000 to $5,500

Rental ID 132307

  • RTR Vacation Rental
  • Lease $4,000 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.

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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: 4.32% last updated on Feb 8, 2018
* 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 $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: 4.32% last updated on Feb 8, 2018
* 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: 4.32% last updated on Feb 8, 2018
* 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$3,300 to $5,000

Rental ID 135243

  • RTR Vacation Rental
  • Lease $3,300 to $5,000
  • 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.

{$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: 4.32% last updated on Feb 8, 2018
* 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: 4.32% last updated on Feb 8, 2018
* 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$1,500 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!

{$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: 4.32% last updated on Feb 8, 2018
* 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 $6,000

Rental ID 136204

  • RTR Vacation Rental
  • Lease $3,000 to $6,000
  • 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

{$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: 4.32% last updated on Feb 8, 2018
* 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$3,500 to $8,000

Rental ID 116772

  • RTR Vacation Rental
  • Lease $3,500 to $8,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 2

Marvelous vintage cottage remodeled to perfection in 1985. Waterfront location with private beach in front along with a 120 foot dock. Professionally decorated interior. Magical setting.

{$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: 4.32% last updated on Feb 8, 2018
* 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$1,600 to $2,300

Rental ID 135213

  • RTR Vacation Rental
  • Lease $1,600 to $2,300
  • 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

{$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: 4.32% last updated on Feb 8, 2018
* 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$6,500 to $9,500

Rental ID 127428

  • RTR Vacation Rental
  • Lease $6,500 to $9,500
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 2

The Pratt House is what downtown Oak Bluffs is all about. Vintage charm and ocean views. Located on Waban park with views of the Inkwell. This five bedroom, 2 bathroom home is perfect for your next visit to the Vineyard!

{$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: 4.32% last updated on Feb 8, 2018
* 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