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$6,000 to $10,000

Rental ID 137764

  • RTR Vacation Rental
  • Lease $6,000 to $10,000
  • 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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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: 4.57% last updated on Jun 21, 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 $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.

{$office->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: 4.57% last updated on Jun 21, 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.

{$office->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: 4.57% last updated on Jun 21, 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$1,300 to $2,300

Rental ID 116503

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

{$office->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: 4.57% last updated on Jun 21, 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$2,800 to $4,950

Rental ID 116762

  • RTR Vacation Rental
  • Lease $2,800 to $4,950
  • 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.

{$office->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: 4.57% last updated on Jun 21, 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 $7,500

Rental ID 136665

  • RTR Vacation Rental
  • Lease $3,500 to $7,500
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 3

Oak Bluffs is the front entry way. The Inkwell Beach is the living room with a large flat screen TV with surround a sound and a dining area, the kitchen area with an island cooking surface it is where all the action happens this flat screen today. . The family room downstairs is named Chilmark where you can play cards, games, or read your favorite book when you want to just “chill”, of course the kids can take over the room for their indoor activities. The bedroom on the main level is named West Tisbury with queen bed and access to the outdoor deck. A full bath is located next to the room with a bath and shower. On the second level you will find the master bedroom named Edgartown, it has king bed and a daybed for watching television or window gazing has an en suite bathroom that includes a shower and tub. Menemsha is the second bedroom and has a double bed next to a beautiful Jack and Jill bathroom with shower. . The Vineyard is the second master and has two queen beds and other exquisite decor.

{$office->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: 4.57% last updated on Jun 21, 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 $4,000

Rental ID 125185

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

{$office->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: 4.57% last updated on Jun 21, 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 $8,500

Rental ID 127105

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

Beautifully appointed brand new four bedroom home. Steps to Niantic park, walk to Inkwell and downtown Oak Bluffs. Central air-conditioning and a lovely farmers porch to sit and watch the world go by.

{$office->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: 4.57% last updated on Jun 21, 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 $4,500

Rental ID 137752

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

In Town 3 Bedroom and 2 Full bath home. Located next to Niantic park and Basketball court, short walk to all Oak Bluffs has to offer - great restaurants, shops and of course the Inkwell beach.

{$office->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: 4.57% last updated on Jun 21, 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!

{$office->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: 4.57% last updated on Jun 21, 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