Oak Bluffs Vacation Rentals

Oak Bluffs is a beautiful peninsula on the north eastern coast of Martha’s Vineyard that is bordered by Nantucket Sound. Renting a vacation home in Oak Bluffs gives you so many options. Our list of vacations rentals include luxury waterfront properties with exceptional views of the sound and quaint Victorian homes that allow you to glimpse deeply into Martha’s Vineyard’s historic past. Vacationing in Oak Bluffs is like taking a trip back in time. Ocean air and private beaches make you feel as though you have Martha’s Vineyard all to yourself.

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Bayes Hill Beauty - Stunning Landscaping, Privately Situated Deck & Patio Association Tennis, Bose Soundock II
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$5,000 - $6,000
June 2025
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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ALLER

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Oak Bluffs 4 Bedroom Home, Walk to Town & Beach!

10-minute walk to Oak Bluffs center and beach area from this lovely modern vacation home.  Enjoy all that the summer community of Oak Bluffs has to offer with quaint shops,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$540 - $6,000
June 2025
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Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
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DAWKN

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Exquisite Designer Home, 10 minute Walk to Oak Bluffs Town Center, Screened Porch, Patio Dining Area, Landscaped Yard, Professionally Decorated, AC

Quietly nestled on a quiet street just on the outskirts of town, this brightly lit home features a mix of coastal details and traditionally styled upscale furnishings for your comfort. The...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$4,400 - $6,000
June 2025
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Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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BOOND

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Wonderful Vacation Home, East Chop Area of Oak Bluffs, Private Yard, Screened Porch, 4 bedrooms, 2 baths.

Nestled on a quiet street in the idyllic East Chop area of Oak Bluffs, this classic New England summer home offers vacationing families and friends a special place to gather...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,600 - $6,000
June 2025
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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DHANM

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Property Details
Adorable Oak Bluffs Cottage Just Over a Mile to the Village Center and Town Beaches, Porch, Deck, 4 Bedrooms, 2 Baths

Nestled on a quiet street, this recently updated residence boasts delightful indoor and outdoor living areas. The entrance porch offers cozy seating with wicker chairs and a small dining table that...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$2,300 - $5,700
June 2025
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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BARNJ

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Property Details
Chic, Meticulously Maintained Cape Style Home. Walk to Oak Bluffs Town Center and Beaches, Tucked on a Large Beautifully Landscaped Lot

Nestled in a beautifully landscaped lot in a serene and private neighborhood, this meticulously maintained cottage in Oak Bluffs, Martha's Vineyard, offers a perfect retreat for rental guests. With chic...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
3
Price Range:
$3,750 - $5,600
June 2025
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Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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HAZAM

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Property Details
The Retreat at Towanticut Where Coastal Elegance Meets Island Serenity, 3 Bedrooms, 2 Baths, Landscaped Yard, Deck Dining Area

Welcome to The Retreat at Towanticut— a chic coastal escape where upscale comfort meets effortless Vineyard charm. Nestled in the heart of Oak Bluffs and just a 15-minute stroll to Circuit Avenue...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$3,000 - $5,600
June 2025
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Clean Fee: 
$350
Tax: State & Local: 
11.7
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WESTW

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Property Details
Tri Level Oak Bluffs Home, Central A/C, Set in Private Community of Sengekontacket, Multiple Living Spaces, Large Deck, Patio Area, Association Tennis

Privately situated on a hilltop in Sengekontacket, -spacious tri-level, 4000 sq ft contemporary home. Set in a wonderful, family friendly community, offering association tennis courts, and an association dock on Sengekontacket Pond...Read more

Location: 
Oak Bluffs
Sleeps: 
14
Bedrooms: 
5
Baths: 
2
Price Range:
$4,400 - $5,500
June 2025
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Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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ARMSA

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Property Details
Cozy Newly updated Seashore Cottage, East Chop Highlands Area, Farmers Porch and Deck

If you are looking for an immaculate, charming, cottage-style, yet modern home close to Oak Bluffs center, look no further. This recently updated 3 bedroom, 2 bath home features sunny open...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,500 - $5,500
June 2025
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Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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ROS22

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Property Details

Set in the heart of Oak Bluffs and on a quiet residential street, this newly updated tastefully decorated vacation home offers rental guests all the comforts of home inside and out....Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
1
Price Range:
$3,000 - $5,500
June 2025
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Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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PEOTA

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Property Details
Pristine Water view Home, Located in the Community of Homes known as Water View Farms, Walk to Private Association Waterfront, Great Play Beach, Launch Kayaks

This charming updated home is set in idyllic Water View Farms overlooking Sengekontacket pond.  This well-thought-out home offers a beautifully landscaped yard and cottage-style living with indoor spaces that transition...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,000 - $5,250
June 2025
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Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
tothg13-03-exterior.jpg
 
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TOTHG

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Property Details
Adorable Updated Vineyard Cottage, Lovely Landscaped Yard, Central A/C, Flat Screen TV, Bike Paths at end of Drive, One Mile to Oak Bluffs Center

Bright and classic summer cottage. Conveniently located just one mile from Oak Bluffs town center, Inkwell Beach, shops, fine and family dining, historic Flying Horses Carousel, public tennis courts, Ocean...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$4,950 - $4,950
June 2025
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Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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TAYLJ

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Property Details
SPACIOUS LIGHTFILLED 3 BEDROOM, 3 BATH HOME, PRIVATE DECK WITH PATIO DINING, LOCATED IN QUIET COMMUNITY OF HOMES

Enjoy the best of the Island—the serenity of a secluded wooded sanctuary, the convenience, fun and shopping of the 3 Down Island towns (Oak Bluffs, Edgartown and Vineyard Haven), and easy access...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$4,000 - $4,900
June 2025
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September 2025
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

 

 

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GLOVL

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Property Details
Lovely Contemporary Home, Quiet Location in Pond View, Private Back Yard, Porch & Deck

Beautifully maintained, family-friendly home.

Lovely 3 Bedroom, 2.5 bath home situated in a quiet enclave of homes known as Pond View and just 2.5 miles to the center of Oak Bluffs....Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$4,700 - $4,900
June 2025
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July 2025
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August 2025
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September 2025
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Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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ST203

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Property Details
Seaview Condominium, Waterview, Walk to Town and Beach

Beachfront Condominium with breathtaking views of Nantucket Sound. Just steps to the beach.Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
2
Price Range:
$2,900 - $4,800
June 2025
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July 2025
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August 2025
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September 2025
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Clean Fee: 
$275 per week
Tax: State & Local: 
11.7

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