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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Seaview Condo Unit, Gorgeous Water Views, In Town Location, Modern updated Interior!

Note: Seavies Condos is a 3-minute walk from the Steamship Authority dock in Oak Bluffs and two blocks from the Island Queen ferry dock. Perfect location if you cannot or...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$14 - $5,103
June 2025
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Clean Fee: 
$230 per week
Tax: State & Local: 
11.7

5 minute walk from Steamship Authority Oak Bluffs dock to the Seaview Condos.  2 blocks from the Island Queen ferry dock.  

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WILCM

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Hidden Cove, Association Tennis Courts, 3 Bedrooms, 2.5 Baths, Screened Porch and Deck

Nestled in the charming Hidden Cove community, this adorable contemporary home resides on a tranquil street within walking distance of the association's tennis courts. Its central location places it just...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$14 - $5,005
June 2025
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Clean Fee: 
$325 per week
Tax: State & Local: 
11.7
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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:
$14 - $4,956
June 2025
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Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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GLOVL

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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:
$14 - $4,900
June 2025
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Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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GRATD

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Property Details
Located in the Heart of Oak Bluffs, 5 Minute Walk to OB Center and 2 Blocks to the Beach
Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
2
Price Range:
$14 - $4,704
June 2025
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Clean Fee: 
$260 per week
Tax: State & Local: 
11.7
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KEANM

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Property Details
Lovely Oak Bluffs Home, 3 Bedrooms, 2.5 Baths, Sleeps 7. Set just on the Outskirts of Oak Bluffs Center

Lovely 3 bedroom, 2.5 bath home that sleeps 7. This sweet home is bordered by a large yard and is located just on the outskirts of Oak Bluffs. The patio...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$14 - $4,704
June 2025
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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DONOP

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Property Details
Hidden Cove, Centrally Located to Beaches and Towns, Association Tennis Courts, A/C, WiFi

Centrally located in the Hidden Cove community of homes on the outskirts of Oak Bluffs. Lovely area to bike, walk, or play tennis at the association courts. 

The main level features an...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$14 - $4,501
June 2025
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Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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KOEOB

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Property Details
Adorable Updated 2 Bedroom 1.5 Bath Cottage, Walk to Town, Harbor and Beach

If you are looking for an adorable cottage-style home in the center of Oak Bluffs this newly updated, tastefully decorated 2 bedroom, with one full bath and a half bath, is sure to...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
1
Price Range:
$14 - $4,501
June 2025
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Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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SACHE

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Property Details
Waterview Farms, Water view

Lovely contemporary home in one of the island's premier community settings, Waterview Farms. Close to Farm Neck Golf Course and tennis and a short distance to town and beaches....Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$14 - $4,165
June 2025
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Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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PETEV

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Property Details
Lovely Waterfront Home, Oak Bluffs, Gorgeous Water Views, Association Tennis Courts, AC, Wi-fi, Bike Paths Nearby

Note: Pricing for this waterfront home takes into account that this is an older-style home. Please note that baths and kitchen have not been updated

MVVR Exclusive! Spacious, traditional waterfront Cape Cod style home...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
4
Baths: 
2
Price Range:
$14 - $4,102
June 2025
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Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
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KLEIB

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Property Details
Lagoon Waterfront & Beachfront, Spectacular Water views, Room A/C, WIFI

Adorable waterfront & beachfront cottage.   Immaculately maintained, lots of summer charm, fantastic views of the Vineyard Sound and Lagoon from the large patio area. Stairs lead directly to a...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$14 - $4,102
June 2025
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Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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MAHAB

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Property Details
Sweet Updated 3 Bedroom Home, Nicely Tucked in Lightly Wooded Area, Central Location, Beaches and Towns just a short Drive!

Lovely reverse contemporary home with a large deck, outdoor dining, and grill area. The upper level of this home features an open kitchen, living, and dining area stylishly furnished.  Nicely equipped kitchen...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
1
Price Range:
$14 - $4,004
June 2025
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Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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CAH48

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Property Details
Classic Lovely Vineyard Cottage, Pristine Condition, Approximately 1.5 Miles to Town and Beaches. Mature Landscaped Yard, Spacious Deck

The Perfect Cozy Cottage, is pristinely maintained and situated in a quiet neighborhood just on the outskirts of Oak Bluffs.  This spacious 2 bedroom, 2 bath home sleeps 4. The...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$14 - $4,004
June 2025
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Clean Fee: 
$300, additional may apply multiple week rentals
Tax: State & Local: 
11.7
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FRANL

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Property Details
Modern, Light filled Home, Located at end of Quiet Street, 1.5 Miles to Oak Bluffs center, Harbor Area and one of many Public Beaches

Perfect Oak Bluffs vacation home.  Located just 1.5 miles to the village center, town beach, and centrally located to the towns of Vineyard Haven, Edgartown, and multiple public beaches.  This...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$14 - $3,605
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: 
$400 per week
Tax: State & Local: 
11.7
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GOLLB

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Property Details
Waterfront, Private Beach, Gorgeous Water Views, Room AC, Wifi

MVVR EXCLUSIVE:  Classic, beach cottage with spectacular views across the sound, calm water swimming, and a great area for kayaking. The open kitchen, dining, and living areas are enhanced by the wall of windows...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
3
Baths: 
1
Price Range:
$14 - $3,304
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: 
$325 per week
Tax: State & Local: 
11.7

Cottage books Tuesday to Tuesday July & August weeks

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