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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New Modern Farmhouse Design, Great Location!, Wraparound Farmers Porch, Deck Area.

Beautiful new 4 bedroom home, 3.5 bath sleeps 8.  Ideally located just 2 miles from the center of Oak Bluffs and just minutes by car to the towns of Vineyard Haven and...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,100 - $6,900
June 2027
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Clean Fee: 
$500 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:
$3,600 - $6,700
June 2027
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 $6,700
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August 2027
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 $5,600
Clean Fee: 
$350 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:
$4,950 - $6,700
June 2027
SuMoTuWeThFrSaWeek
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$4,950
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$4,950
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 $5,300
July 2027
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$5,500
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$5,500
August 2027
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$6,200
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 $6,700
September 2027
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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THORB

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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:
$6,500 - $6,500
June 2027
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Clean Fee: 
$575 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 - $6,500
June 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
July 2027
SuMoTuWeThFrSaWeek
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August 2027
SuMoTuWeThFrSaWeek
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$6,500
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 $5,000
September 2027
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 $5,000
Clean Fee: 
$380 per week
Tax: State & Local: 
11.7
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LONGK

Inquire
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:
$6,000 - $6,000
June 2027
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September 2027
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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CENCP

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Property Details
East Chop Waterfront, Extraordinary Sunsets &Views Across the Sound , Deck directly on the Beach, Casual Interior

Classic, casual beachfront home combines cottage styling with modern amenities. spectacular views, quietly lapping waves right outside your windows, and breathtaking sunsets. Ideally located in the East Chop Area of Oak Bluffs just a short distance...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$6,000 - $6,000
June 2027
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September 2027
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Clean Fee: 
$480 per week
Tax: State & Local: 
11.7

 

 

 

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DAWKN

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Property Details
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:
$5,050 - $6,000
June 2027
SuMoTuWeThFrSaWeek
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$5,300
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$5,300
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$5,300
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$5,400
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 $6,000
July 2027
SuMoTuWeThFrSaWeek
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$6,000
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$6,000
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$6,000
August 2027
SuMoTuWeThFrSaWeek
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$6,000
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$6,000
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 $6,000
September 2027
SuMoTuWeThFrSaWeek
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$6,000
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$5,100
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$5,100
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$5,100
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 $5,100
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
Add Favorite
 
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ROBIH

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

Note: Seaview 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 do...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,100 - $6,000
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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$5,800
August 2027
SuMoTuWeThFrSaWeek
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$6,000
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$7,200
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$7,200
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$5,000
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 $2,950
September 2027
SuMoTuWeThFrSaWeek
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$2,950
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$2,950
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$2,950
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$2,950
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 $2,950
Clean Fee: 
$300 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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SAUNJ

Inquire
Property Details
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$2,500 - $6,000
June 2027
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$4,000
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 $5,000
July 2027
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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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$8,000
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$6,000
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 $6,000
September 2027
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$3,000
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$3,000
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 $3,000
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
Add Favorite
 
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CLARO

Inquire
Property Details
Contemporary Farmhouse Design, Multiple Living Areas, Screened Porch & Farmers Porch, Deck, Lovely Yard Area, Bike or Walk to Oak Bluffs Center.

Contemporary Farmhouse Design | Multiple Living Areas | Screened Porch, Farmer’s Porch & Deck | Walk or Bike to Oak Bluffs Center

Located just on the outskirts of Oak Bluffs,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,100 - $5,900
June 2027
SuMoTuWeThFrSaWeek
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3
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$3,300
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$3,300
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$3,600
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$4,300
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 $5,300
July 2027
SuMoTuWeThFrSaWeek
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$5,300
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$5,300
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$5,300
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$5,300
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$5,900
August 2027
SuMoTuWeThFrSaWeek
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$6,100
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$6,100
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$5,900
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$5,000
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 $3,600
September 2027
SuMoTuWeThFrSaWeek
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$3,600
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$3,600
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$3,100
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$3,100
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30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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HAZAM

Inquire
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:
$4,350 - $5,850
June 2027
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September 2027
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Clean Fee: 
$500
Tax: State & Local: 
11.7
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FRIEM

Inquire
Property Details
Beautiful East Chop Home , Walk to Town & Beach, Outdoor Patio Area with Patio Dining

 Lovely Spacious East Chop Area home features elegant custom craftsmanship throughout, a light-filled open kitchen, living and dining areas, and a family/TV room. 3 bedrooms on the 2nd level and 2...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$5,750 - $5,750
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSaWeek
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$5,750
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$5,750
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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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September 2027
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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GOLDF

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Property Details
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:
$5,500 - $5,500
June 2027
SuMoTuWeThFrSaWeek
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$8,300
27
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29
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 $10,500
July 2027
SuMoTuWeThFrSaWeek
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2
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$10,500
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$10,500
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$11,000
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$11,000
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$11,500
August 2027
SuMoTuWeThFrSaWeek
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$11,500
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$11,500
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$11,500
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$9,500
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 $9,000
September 2027
SuMoTuWeThFrSaWeek
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$9,000
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$5,500
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$5,500
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$5,500
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 $5,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

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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FISHJ

Inquire
Property Details
Stylish Contemporary Vacation Home situated in Meadow View Farms, Open Light Filled Design, Expansive Private Deck

Come and enjoy this light-filled, beautifully maintained, three-level contemporary home complete with gardens, landscaped yard, and a children’s backyard playground.  

The main level features an open kitchen, dining, and TV/living...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$3,500 - $5,500
June 2027
SuMoTuWeThFrSaWeek
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2
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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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 $6,900
July 2027
SuMoTuWeThFrSaWeek
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2
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$6,900
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$6,900
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$6,900
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$6,900
25
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$6,900
August 2027
SuMoTuWeThFrSaWeek
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2
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$6,900
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$6,900
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$6,900
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$6,900
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 $6,900
September 2027
SuMoTuWeThFrSaWeek
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$6,900
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$5,500
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$5,200
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$5,200
26
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 $5,200
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

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