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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Outstanding Oak Bluffs Summer Home with Heated Pool and Patio Surround, Screened Porch with Living and Dining Area, Association Tennis Courts.

MVVR Exclusive Listing:  Set in a quiet community of homes just on the outskirts of OB, this outstanding home provides a peaceful getaway yet is just a short drive to the...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
5
Baths: 
3
Price Range:
$9,000 - $9,000
June 2027
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July 2027
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$12,000
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$12,000
August 2027
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$14,000
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$14,000
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$14,000
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$12,000
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 $9,000
September 2027
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$9,000
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Clean Fee: 
$600 per week
Tax: State & Local: 
14.45

Pool Heated to 80 July & August and the 1st week in September included in the rental rate!

 

Pool Heated to 80  May, June & September weeks at additional cost ($400). 

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PRIAN~

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Property Details
Beautiful Upscale Contemporary Home, Designer Details Throughout, 4 Bedrooms, 4.5 Baths, Muliple Living Areas

Discover this stunning tri-level vacation home nestled in a peaceful community just on the outskirts of Oak Bluffs and minutes away from Oak Bluffs center, Edgartown Village, downtown Vineyard Haven, and several...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
4
Price Range:
$8,300 - $8,750
June 2027
SuMoTuWeThFrSaWeek
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 $8,300
July 2027
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$8,300
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$8,500
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$8,500
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$8,750
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August 2027
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$9,900
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$9,900
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$8,750
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September 2027
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Clean Fee: 
$750 per week
Tax: State & Local: 
14.45
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WHARG~

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Property Details
Lovely Home in a quiet Neighborhood. Walk to Town Center and Inkwell Beach, Large Private Deck, Room AC

Spacious sun-filled contemporary home located on a quiet private street, a 10-minute walk to town center, Inkwell Beach, and the harborfront.

The first level features a spacious kitchen with stainless steel...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$7,200 - $8,500
June 2027
SuMoTuWeThFrSaWeek
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$7,200
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$7,200
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$7,200
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$7,200
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 $7,200
July 2027
SuMoTuWeThFrSaWeek
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$7,200
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$7,500
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$7,500
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$7,500
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$7,500
August 2027
SuMoTuWeThFrSaWeek
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$8,500
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$8,500
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$8,500
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$8,500
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 $8,500
September 2027
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$8,500
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Clean Fee: 
$375 per week
Tax: State & Local: 
14.45
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MILTD

Inquire
Property Details
Perfect in Town Location. Just 1 to 2 blocks to Beach, Town Center & Harbor Area, Walk to and from the Ferry

Centrally located in the heart of Oak Bluffs, walk 1-2 blocks to the beach, public tennis courts, and town & harbor areas. This wonderful large home has a large wrap-around porch for relaxing, 7...Read more

Location: 
Oak Bluffs
Sleeps: 
14
Bedrooms: 
7
Baths: 
3
Price Range:
$8,500 - $8,500
June 2027
SuMoTuWeThFrSaWeek
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$9,500
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$9,500
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$9,500
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$9,500
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 $13,500
July 2027
SuMoTuWeThFrSaWeek
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$13,500
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$13,500
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$13,500
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$13,500
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$13,500
August 2027
SuMoTuWeThFrSaWeek
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$13,500
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$13,500
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$13,500
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$13,500
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 $12,500
September 2027
SuMoTuWeThFrSaWeek
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$12,500
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$12,500
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$12,500
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$12,500
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30
 $12,500
Clean Fee: 
$500 per week
Tax: State & Local: 
14.45
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BOWDL~

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Property Details
Lovely Custom Contemporary Home, Tucked in the Community of Bayes Hill, 4 Bedrooms, 4 Bath, Landscaped, Deck, Patio Dining Area

Designed with a sophisticated contemporary aesthetic, this chic vacation retreat showcases an open floor plan, expansive windows, and beautifully curated interiors. Offering four bedrooms and 3.5 baths, the home is...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$7,000 - $8,050
June 2027
SuMoTuWeThFrSaWeek
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$7,500
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$7,500
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$7,500
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$7,500
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 $7,750
July 2027
SuMoTuWeThFrSaWeek
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$7,750
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$7,750
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$7,750
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$7,750
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$8,050
August 2027
SuMoTuWeThFrSaWeek
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$8,050
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$8,050
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$8,050
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$8,050
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 $8,050
September 2027
SuMoTuWeThFrSaWeek
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$8,050
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$7,500
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$7,500
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$7,500
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30
 $7,500
Clean Fee: 
$500 per week
Tax: State & Local: 
14.45
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WESTC~

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Property Details
Summer Wind in the Heart of Oak Bluffs, Water views. 2 minute Walk to Inkwell Beach & 5 minute walk to town, All Newly Remodeled 5 Bedroom, 3 Bath Home With Deluxe Amenities

Set in the heart of Oak Bluffs center, this newly renovated home features water views, walk to Inkwell Beach and Pay Beach and walk to the town center all within...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$7,000 - $8,000
June 2027
SuMoTuWeThFrSaWeek
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$8,000
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$8,000
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$9,000
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$10,000
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 $12,000
July 2027
SuMoTuWeThFrSaWeek
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$12,000
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$13,000
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$14,000
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$14,000
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$15,000
August 2027
SuMoTuWeThFrSaWeek
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$22,000
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$22,000
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$22,000
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$14,000
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 $9,500
September 2027
SuMoTuWeThFrSaWeek
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$9,500
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$8,000
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$8,500
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$8,500
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 $7,000
Clean Fee: 
$550
Tax: State & Local: 
14.45
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JOHNL~

Inquire
Property Details
"Endless Summer Vacation" Stylish, Newly Updated 3 + Bedroom, Sleeps 8, East Chop Area of Oak Bluffs, Deck Living & Dining Area, Screened Porch
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$3,500 - $8,000
June 2027
SuMoTuWeThFrSaWeek
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$3,500
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$3,500
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$4,000
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$4,000
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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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$5,500
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$6,000
August 2027
SuMoTuWeThFrSaWeek
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$8,000
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$8,000
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$8,200
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$6,500
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 $5,500
September 2027
SuMoTuWeThFrSaWeek
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$5,500
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$5,500
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$5,000
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$5,000
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 $5,000
Clean Fee: 
$450 per week
Tax: State & Local: 
14.45
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BURBR

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Property Details
Perfect Retreat for Large Families, 1.5 miles to Oak Bluffs Town Center & Beach, Bike Path at end of Street

Spacious and perfect for extended families, featuring multiple attractively furnished living areas, and sleeps 13 comfortably. The lower level of the house features a queen bed, kitchenette, den area with...Read more

Location: 
Oak Bluffs
Sleeps: 
11
Bedrooms: 
5
Baths: 
3
Price Range:
$7,950 - $7,950
June 2027
SuMoTuWeThFrSa
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July 2027
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$7,950
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$7,950
August 2027
SuMoTuWeThFrSaWeek
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$7,950
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$7,950
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$7,950
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$7,950
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 $7,950
September 2027
SuMoTuWeThFrSaWeek
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$7,950
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$7,950
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$7,950
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$7,950
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30
 $7,950
Clean Fee: 
$450 per week
Tax: State & Local: 
14.45
Add Favorite
 
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CASHK

Inquire
Property Details
Lovely Home, Centrally Located, Bike Paths, AC all Rooms

This lovely 3 bedroom home features an open floor plan on the living level, colorful decor, window AC in all rooms, and a well-equipped modern kitchen. The home is nicely situated...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
2
Price Range:
$7,500 - $7,800
June 2027
SuMoTuWeThFrSaWeek
 1
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 $7,500
July 2027
SuMoTuWeThFrSaWeek
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$7,500
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$7,500
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$7,500
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$7,500
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$7,500
August 2027
SuMoTuWeThFrSaWeek
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$7,800
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$7,800
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$7,800
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$7,800
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31
 
September 2027
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Clean Fee: 
$325 per week
Tax: State & Local: 
14.45
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VANAL

Inquire
Property Details
Classic Updated Gingerbread Cottage, 5 Minute Stroll Along Harbor to Beach and Town Center,

Classic Vineyard Oak Bluffs Cottage, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. The main living level features a lovely kitchen, very well stocked with...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,500 - $7,500
June 2027
SuMoTuWeThFrSaWeek
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5
$3,500
6
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$3,500
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$3,500
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$3,500
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 $4,000
July 2027
SuMoTuWeThFrSaWeek
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$4,000
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$5,000
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$4,500
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$4,500
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$5,000
August 2027
SuMoTuWeThFrSaWeek
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$7,500
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$7,500
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$7,500
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$7,500
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30
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 $4,500
September 2027
SuMoTuWeThFrSaWeek
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$4,500
5
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$4,500
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$3,500
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$3,500
26
27
28
29
30
 $3,500
Clean Fee: 
$350 ($275 for interim cleaning on multiple week rentals)
Tax: State & Local: 
14.45
Add Favorite
 
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PETEO~

Inquire
Property Details
Beautiful Custom Built Home Overlooking Little Duarte Pond, Beautifully Landscaped

Outstanding vacation home, centrally located to all three down-island town centers and multiple public beaches. This lovely home in a serene setting overlooks the picturesque Little Duarte Pond in the Iron Hill...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
5
Price Range:
$7,500 - $7,500
June 2027
SuMoTuWeThFrSaWeek
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2
3
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5
6
7
8
9
10
11
12
13
14
15
16
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21
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25
26
$5,000
27
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29
30
 $6,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$6,000
4
5
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$7,500
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$8,500
August 2027
SuMoTuWeThFrSaWeek
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$12,000
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$12,000
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$9,900
29
30
31
 
September 2027
SuMoTuWeThFrSa
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29
30
 
Clean Fee: 
$575 per week
Tax: State & Local: 
14.45
Add Favorite
 
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VANA2~

Inquire
Property Details
Charming , Modern In-Town Oak Bluffs Vacation Home. Walk to Town, Parks, Beach. 4 Bedrooms, Sleeps 8, 3 Baths

This charming Oak Bluffs home is tucked away in a peaceful neighborhood, yet conveniently located just a 10-minute walk to the heart of town, the harbor, and the beach. Meticulously...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$5,000 - $7,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
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$5,000
20
21
22
23
24
25
26
$5,000
27
28
29
30
 $5,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,000
4
5
6
7
8
9
10
$6,500
11
12
13
14
15
16
17
$6,000
18
19
20
21
22
23
24
$6,500
25
26
27
28
29
30
31
$7,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,500
8
9
10
11
12
13
14
$9,500
15
16
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20
21
$9,500
22
23
24
25
26
27
28
$6,500
29
30
31
 $5,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
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$5,000
5
6
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$5,000
12
13
14
15
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17
18
19
20
21
22
23
24
25
26
27
28
29
30
 $4,500
Clean Fee: 
$450 per week
Tax: State & Local: 
14.45
Add Favorite
 
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BARNJ~

Inquire
Property Details
Chic, Meticulously Maintained Cape Style Home, 3 bedrooms, 3 Baths, Sleeps 6, Walk to Oak Bluffs Town Center and Beaches, Tucked on a Large Beautifully Landscaped Lot

Nestled on a beautifully landscaped lot in a serene and private neighborhood, this meticulously maintained home in Oak Bluffs offers a perfect retreat for rental guests, with chic luxury amenities, and mulitiple...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$3,220 - $7,350
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,220
6
7
8
9
10
11
12
$3,220
13
14
15
16
17
18
19
$5,510
20
21
22
23
24
25
26
$5,510
27
28
29
30
 $6,610
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$6,610
4
5
6
7
8
9
10
$6,610
11
12
13
14
15
16
17
$7,350
18
19
20
21
22
23
24
$7,350
25
26
27
28
29
30
31
$7,350
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$7,350
8
9
10
11
12
13
14
$7,350
15
16
17
18
19
20
21
$7,350
22
23
24
25
26
27
28
$6,610
29
30
31
 $6,610
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,610
5
6
7
8
9
10
11
$6,610
12
13
14
15
16
17
18
$3,220
19
20
21
22
23
24
25
$3,220
26
27
28
29
30
 $3,220
Clean Fee: 
$425 per week
Tax: State & Local: 
14.45
Add Favorite
 
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LONGK

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Property Details
Bayes Hill Beauty - Stunning Landscaping, Privately Situated Deck & Patio Association Tennis

Note: Caretaker lives in apartment above the garage. Renter's privacy respected.  Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,600 - $7,200
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,100
6
7
8
9
10
11
12
$5,200
13
14
15
16
17
18
19
$5,400
20
21
22
23
24
25
26
$5,400
27
28
29
30
 $7,200
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$7,200
4
5
6
7
8
9
10
$7,200
11
12
13
14
15
16
17
$7,200
18
19
20
21
22
23
24
$7,200
25
26
27
28
29
30
31
$7,200
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$7,200
8
9
10
11
12
13
14
$7,200
15
16
17
18
19
20
21
$7,200
22
23
24
25
26
27
28
$7,200
29
30
31
 $7,200
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,200
5
6
7
8
9
10
11
$6,000
12
13
14
15
16
17
18
$6,000
19
20
21
22
23
24
25
$6,000
26
27
28
29
30
 $6,000
Clean Fee: 
$450 per week
Tax: State & Local: 
14.45
Add Favorite
 
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BICKE

Inquire
Property Details
East Chop Area, Tri-Level Home with Distant Water views, Located just 1.5 Mi to Oak Bluffs Center

East Chop Escape with lovely Distant Water Views
Light-Filled Tri-Level Home, 4 Bedrooms, & 3 baths, 1.5 Miles to Oak Bluffs Center

Set in the highly sought-after East Chop neighborhood,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,500 - $7,150
June 2027
SuMoTuWeThFrSaWeek
 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
 $7,150
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$7,150
4
5
6
7
8
9
10
$7,150
11
12
13
14
15
16
17
$7,150
18
19
20
21
22
23
24
$7,150
25
26
27
28
29
30
31
$7,150
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$7,150
8
9
10
11
12
13
14
$7,150
15
16
17
18
19
20
21
$7,150
22
23
24
25
26
27
28
$7,150
29
30
31
 $7,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,000
5
6
7
8
9
10
11
$6,500
12
13
14
15
16
17
18
$6,500
19
20
21
22
23
24
25
$6,500
26
27
28
29
30
 $6,500
Clean Fee: 
$600 per week
Tax: State & Local: 
14.45

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