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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Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$5,250 - $5,250
June 2027
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Clean Fee: 
$500 per week
Tax: State & Local: 
14.45
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TAYLJ~

Inquire
Property Details
SPACIOUS LIGHTFILLED 3 BEDROOM, 3 BATH HOME, PRIVATE DECK WITH PATIO DINING, 7 MINUTE DRIVE TO THE CENTER OF OAK BLUFFS AND INKWELL BEACH

Experience the best of Island living—peaceful residential surroundings, the vibrant shops and attractions of the three Down Island towns (Oak Bluffs, Edgartown, and Vineyard Haven), and quick access to public...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$2,700 - $5,200
June 2027
SuMoTuWeThFrSaWeek
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2
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$3,900
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$3,900
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$3,900
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$4,300
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 $4,500
July 2027
SuMoTuWeThFrSaWeek
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$4,500
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$4,500
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$4,500
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$4,500
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$4,500
August 2027
SuMoTuWeThFrSaWeek
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$5,500
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$5,500
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$5,500
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$5,500
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 $5,200
September 2027
SuMoTuWeThFrSaWeek
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$5,200
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$3,700
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$3,200
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$3,200
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30
 $3,200
Clean Fee: 
$450 per week
Tax: State & Local: 
14.45

 

 

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DENAL~

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Property Details

Charming, 4-bedroom Oak Bluffs Home, pristinely maintained!  The large wraparound porch and backyard patio areas provide the perfect venue for relaxing when not at the beach or out and about...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,000 - $5,000
June 2027
SuMoTuWeThFrSaWeek
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$3,000
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$3,000
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$3,000
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$3,000
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 $5,000
July 2027
SuMoTuWeThFrSaWeek
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$5,000
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$5,000
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$5,000
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$5,000
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$5,000
August 2027
SuMoTuWeThFrSaWeek
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$5,000
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$5,000
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$5,000
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$5,000
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 $4,000
September 2027
SuMoTuWeThFrSaWeek
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$4,000
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$2,000
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$2,000
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$2,000
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 $2,000
Clean Fee: 
$400 per week
Tax: State & Local: 
14.45

Parking for two cars only, no on-street parking!

 

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TOTHG

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Property Details

Note: Older style TVs seen in photos have been replaced. 

This bright and classic summer cottage is ideally located just one mile from Oak Bluffs town center and all the...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$4,000 - $4,950
June 2027
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July 2027
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$4,950
August 2027
SuMoTuWeThFrSaWeek
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$4,950
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$4,950
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$4,950
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$4,950
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 $4,000
September 2027
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$4,000
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$4,000
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 $4,000
Clean Fee: 
$250 per week
Tax: State & Local: 
14.45
Add Favorite
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GRATD~

Inquire
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:
$3,400 - $4,800
June 2027
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$4,100
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$4,400
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 $4,800
July 2027
SuMoTuWeThFrSaWeek
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$4,800
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$4,800
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$4,800
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$4,800
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$4,800
August 2027
SuMoTuWeThFrSaWeek
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$4,800
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$4,800
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$4,800
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$4,800
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 $4,800
September 2027
SuMoTuWeThFrSaWeek
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$4,800
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$4,200
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$4,000
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$3,400
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29
30
 
Clean Fee: 
$270 per week
Tax: State & Local: 
14.45
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KEANM~

Inquire
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:
$2,000 - $4,800
June 2027
SuMoTuWeThFrSaWeek
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$2,500
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$2,500
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$3,000
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$3,000
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 $4,800
July 2027
SuMoTuWeThFrSaWeek
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$4,800
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$4,800
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$4,800
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$4,800
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August 2027
SuMoTuWeThFrSaWeek
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$5,000
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$5,000
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$5,000
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$5,000
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 $4,500
September 2027
SuMoTuWeThFrSaWeek
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$4,500
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30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
14.45
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COWAC~

Inquire
Property Details
Lovely Cape, 7 minute walk to town and harbor area, 4 bedrooms, 3 baths, sleeps 7

Lovely 4 bedroom, 3 bath home, pristinely maintained and ideally located just on the outskirts of Oak Bluffs on a quiet street. Short walk to town center and Oak Bluffs town...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
3
Price Range:
$3,000 - $4,700
June 2027
SuMoTuWeThFrSaWeek
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$3,000
6
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$3,000
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$3,000
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$3,800
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 $4,700
July 2027
SuMoTuWeThFrSaWeek
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$4,700
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$4,700
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$4,700
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$4,700
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$5,350
August 2027
SuMoTuWeThFrSaWeek
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$5,400
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$5,600
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$5,400
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$4,400
29
30
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 $3,200
September 2027
SuMoTuWeThFrSaWeek
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$3,200
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$3,200
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$3,000
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$3,000
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29
30
 $3,000
Clean Fee: 
$450 per week
Tax: State & Local: 
14.45
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KOEOB~

Inquire
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:
$1,900 - $4,600
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,600
6
7
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12
$2,600
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$2,800
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$2,800
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 $3,900
July 2027
SuMoTuWeThFrSaWeek
 1
2
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$3,900
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$3,900
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$3,900
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$3,900
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$3,900
August 2027
SuMoTuWeThFrSaWeek
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$4,600
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$4,600
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 $3,100
September 2027
SuMoTuWeThFrSaWeek
 1
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$3,100
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 $2,600
Clean Fee: 
$275 per week
Tax: State & Local: 
14.45
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THORB~

Inquire
Property Details
Contemporary 4 Bedroom, 4 Bath, Multiple Living Spaces, Walk to Oak Bluffs Center and Inkwell Beach-10 minutes

Perfect for extended families and friends, this spacious tri-level contemporary home offers multiple gathering spaces, comfortable accommodations, and an ideal location just a short stroll from the heart of Oak Bluffs....Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$4,000 - $4,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
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5
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9
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12
$4,000
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$4,000
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$4,500
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30
 $5,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
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$5,500
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$6,500
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$6,500
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$6,500
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$6,500
August 2027
SuMoTuWeThFrSaWeek
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$7,500
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$8,800
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$8,800
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$7,500
29
30
31
 $5,500
September 2027
SuMoTuWeThFrSaWeek
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$5,500
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$4,000
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$4,000
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$4,000
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29
30
 $4,000
Clean Fee: 
$600 per week
Tax: State & Local: 
14.45
Add Favorite
 
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WILCM~

Inquire
Property Details
Hidden Cove Retreat, Walk to Association Tennis/Pickleball 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/pickleball courts. Its central location places it just a...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$4,000 - $4,500
June 2027
SuMoTuWeThFrSaWeek
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 $4,500
July 2027
SuMoTuWeThFrSaWeek
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$4,500
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$4,500
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$4,500
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$4,500
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$4,500
August 2027
SuMoTuWeThFrSaWeek
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$6,500
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$6,500
15
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$5,000
22
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$5,000
29
30
31
 $4,000
September 2027
SuMoTuWeThFrSaWeek
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$4,000
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29
30
 
Clean Fee: 
$350 per week
Tax: State & Local: 
14.45
Add Favorite
 
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BEG21

Inquire
Property Details
Ideally located just 1 mile to OB Center, Many Updates, Enclosed Private Back Yard, Deck Nicely outfitted with Dining and new Living Area Grouping., Central AC

This cozy recently updated vacation home is tucked on a quiet street just on the outskirts of Oak Bluffs Center. Bike or walk to the town center, Inkwell Beach, and the picturesque Harbor...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$4,500 - $4,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,500
6
7
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9
10
11
12
$4,500
13
14
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$4,500
20
21
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23
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25
26
$4,500
27
28
29
30
 $6,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$6,500
4
5
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$7,000
11
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$7,000
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$7,000
25
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30
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$7,000
August 2027
SuMoTuWeThFrSaWeek
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$8,000
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$8,000
15
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$8,000
22
23
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25
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28
$8,000
29
30
31
 $3,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,500
5
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$3,500
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$3,500
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25
$3,500
26
27
28
29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
14.45

Note: Owner maintains security camera on front of house

Add Favorite
 
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DONOP~

Inquire
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:
$2,400 - $4,300
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,400
6
7
8
9
10
11
12
$3,050
13
14
15
16
17
18
19
$3,050
20
21
22
23
24
25
26
$3,200
27
28
29
30
 $4,100
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,100
4
5
6
7
8
9
10
$4,100
11
12
13
14
15
16
17
$4,300
18
19
20
21
22
23
24
$4,300
25
26
27
28
29
30
31
$4,600
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,720
8
9
10
11
12
13
14
$4,720
15
16
17
18
19
20
21
$4,720
22
23
24
25
26
27
28
$3,570
29
30
31
 $4,100
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,100
5
6
7
8
9
10
11
$4,100
12
13
14
15
16
17
18
$4,100
19
20
21
22
23
24
25
$4,100
26
27
28
29
30
 $4,100
Clean Fee: 
$375 per week
Tax: State & Local: 
14.45
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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:
$2,800 - $4,160
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,100
6
7
8
9
10
11
12
$3,100
13
14
15
16
17
18
19
$3,100
20
21
22
23
24
25
26
$3,100
27
28
29
30
 $3,850
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,850
4
5
6
7
8
9
10
$3,850
11
12
13
14
15
16
17
$3,850
18
19
20
21
22
23
24
$3,850
25
26
27
28
29
30
31
$3,850
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,160
8
9
10
11
12
13
14
$4,160
15
16
17
18
19
20
21
$4,160
22
23
24
25
26
27
28
$4,160
29
30
31
 $4,160
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,160
5
6
7
8
9
10
11
$3,800
12
13
14
15
16
17
18
$3,800
19
20
21
22
23
24
25
$3,800
26
27
28
29
30
 $3,800
Clean Fee: 
$250 per week
Tax: State & Local: 
14.45
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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

MVVR Exclusive! Spacious, traditional waterfront Cape Cod style home tucked away on the shores of Sengekontacket Lagoon in a community of homes - featuring gorgeous views, mini-split AC units in main living areas,...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
4
Baths: 
2
Price Range:
$2,700 - $4,100
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,700
6
7
8
9
10
11
12
$2,700
13
14
15
16
17
18
19
$3,000
20
21
22
23
24
25
26
$3,000
27
28
29
30
 $3,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,500
4
5
6
7
8
9
10
$4,100
11
12
13
14
15
16
17
$3,900
18
19
20
21
22
23
24
$3,900
25
26
27
28
29
30
31
$4,100
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,100
8
9
10
11
12
13
14
$4,100
15
16
17
18
19
20
21
$4,100
22
23
24
25
26
27
28
$4,100
29
30
31
 $3,400
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,400
5
6
7
8
9
10
11
$2,800
12
13
14
15
16
17
18
$2,800
19
20
21
22
23
24
25
$2,800
26
27
28
29
30
 $2,800
Clean Fee: 
$475 per week
Tax: State & Local: 
14.45
Add Favorite
rolaj13-01-patio.jpg
 
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ROLAJ

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Property Details
Waterfront, Water View, Lagoon Beach

This charming, recently renovated, waterfront home atop the lagoon bluffs, boasts spectacular sunsets and panoramic waterfront views of the Lagoon, outer Vineyard Haven Harbor, and Cape Cod from patios, living...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,000 - $4,000
June 2027
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
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22
23
24
25
26
27
28
29
30
 
July 2027
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
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21
22
23
24
25
26
27
28
29
30
31
August 2027
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
September 2027
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$250 per week
Tax: State & Local: 
14.45

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