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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Set Just on the ouskirts of Oak Bluffs. Central AC, Screened Porch

Lovely spacious 3+ bedroom, 3.5 bedroom home within a mile from Oak Bluffs center and beach area.  Fully furnished screen porch and shady porch.  This lovely home sleeps families of 8 comfortably.

The main...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$10 - $6,000
June 2025
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 $6,000
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Clean Fee: 
$425 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:
$10 - $6,000
June 2025
SuMoTuWeThFrSaWeek
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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 2025
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 $6,000
September 2025
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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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BOOND

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Property Details
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:
$10 - $6,000
June 2025
SuMoTuWeThFrSaWeek
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$4,200
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$4,200
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$4,200
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$4,200
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 $5,200
July 2025
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$5,200
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$5,200
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$5,500
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$5,500
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 $6,000
August 2025
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$6,000
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 $6,000
September 2025
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$5,000
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 $5,000
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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THOMS

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Property Details
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:
$10 - $5,820
June 2025
SuMoTuWeThFrSaWeek
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$3,800
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$3,800
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$3,800
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$5,500
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 $6,300
July 2025
SuMoTuWeThFrSaWeek
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$6,300
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$6,300
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 $6,800
August 2025
SuMoTuWeThFrSaWeek
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$6,800
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$6,800
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$6,800
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$6,800
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 $5,820
September 2025
SuMoTuWeThFrSaWeek
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$3,800
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$3,800
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$3,800
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 $3,800
Clean Fee: 
$425 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:
$10 - $5,500
June 2025
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$5,500
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$5,500
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July 2025
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September 2025
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$5,500
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 $3,500
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:
$10 - $5,500
June 2025
SuMoTuWeThFrSaWeek
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$4,000
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 $5,000
July 2025
SuMoTuWeThFrSaWeek
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 $5,500
August 2025
SuMoTuWeThFrSaWeek
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$5,500
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$5,500
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 $4,000
September 2025
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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 $3,000
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
Add Favorite
 
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COWAC

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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:
$10 - $5,250
June 2025
SuMoTuWeThFrSaWeek
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$3,000
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$3,000
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$3,000
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$3,800
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 $4,600
July 2025
SuMoTuWeThFrSaWeek
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$4,600
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$4,600
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$4,600
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$4,600
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 $5,250
August 2025
SuMoTuWeThFrSaWeek
 1
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$5,250
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$5,300
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$5,500
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$5,300
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$4,300
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 $3,200
September 2025
SuMoTuWeThFrSaWeek
 1
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$3,200
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$3,200
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$3,000
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$3,000
28
29
30
 $3,000
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
Add Favorite
 
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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:
$10 - $5,250
June 2025
SuMoTuWeThFrSaWeek
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$3,500
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$3,500
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$4,000
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$4,720
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 $5,250
July 2025
SuMoTuWeThFrSaWeek
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$5,250
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$5,250
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$5,250
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$5,250
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 $5,770
August 2025
SuMoTuWeThFrSaWeek
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$5,770
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$5,770
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$5,770
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$5,770
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$4,720
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 $3,500
September 2025
SuMoTuWeThFrSaWeek
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$3,500
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$3,000
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$3,000
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$2,500
28
29
30
 $2,000
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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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:
$10 - $5,250
June 2025
SuMoTuWeThFrSaWeek
1
2
3
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7
$2,500
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$2,500
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$2,500
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$2,500
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 $3,500
July 2025
SuMoTuWeThFrSaWeek
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$3,500
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$3,000
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$3,000
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$3,000
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 $3,000
August 2025
SuMoTuWeThFrSaWeek
 1
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$3,000
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$5,000
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$5,750
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$5,750
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30
$5,250
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 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
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$4,000
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$2,000
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$2,000
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$2,000
28
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 $2,000
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

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

 

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TRAVM

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Property Details
Updated East Chop Area Summer Retreat, Great Proximity to Town Center and Beaches, Cottage Styling with All the Modern Amenities, Central A/C. Covered Porch and Open Patio Areas.

Visitors will enjoy this delightful &  comfortable 4 bedroom, 3 bath home in the desirable East Chop area of Oak Bluffs. 

Relax in the breeze with your morning coffee on the front...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$10 - $5,200
June 2025
SuMoTuWeThFrSaWeek
1
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 $5,200
July 2025
SuMoTuWeThFrSaWeek
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$5,200
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$5,200
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$5,200
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$5,200
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 $6,800
August 2025
SuMoTuWeThFrSaWeek
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$6,800
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$7,000
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$7,250
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September 2025
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29
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Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
Add Favorite
 
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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:
$10 - $5,100
June 2025
SuMoTuWeThFrSaWeek
1
2
3
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$4,000
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$4,000
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$4,000
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$4,000
29
30
 $4,500
July 2025
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
27
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30
31
 $4,900
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,900
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$5,100
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$5,100
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$5,100
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25
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29
30
$4,900
31
 $4,500
September 2025
SuMoTuWeThFrSaWeek
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2
3
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$4,500
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$4,500
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16
17
18
19
20
$4,000
21
22
23
24
25
26
27
$4,000
28
29
30
 $4,000
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:
$10 - $5,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,000
8
9
10
11
12
13
14
$3,000
15
16
17
18
19
20
21
$3,000
22
23
24
25
26
27
28
$3,600
29
30
 $4,200
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,200
6
7
8
9
10
11
12
$4,200
13
14
15
16
17
18
19
$4,200
20
21
22
23
24
25
26
$4,200
27
28
29
30
31
 $4,200
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,200
3
4
5
6
7
8
9
$5,000
10
11
12
13
14
15
16
$5,700
17
18
19
20
21
22
23
$5,000
24
25
26
27
28
29
30
$5,000
31
 $4,900
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,900
7
8
9
10
11
12
13
$3,000
14
15
16
17
18
19
20
$3,000
21
22
23
24
25
26
27
$3,000
28
29
30
 $2,300
Clean Fee: 
$450 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:
$10 - $4,950
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,700
8
9
10
11
12
13
14
$3,000
15
16
17
18
19
20
21
$4,950
22
23
24
25
26
27
28
$4,950
29
30
 $4,950
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,950
6
7
8
9
10
11
12
$4,950
13
14
15
16
17
18
19
$4,950
20
21
22
23
24
25
26
$4,950
27
28
29
30
31
 $4,950
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,950
3
4
5
6
7
8
9
$4,950
10
11
12
13
14
15
16
$4,950
17
18
19
20
21
22
23
$4,950
24
25
26
27
28
29
30
$4,950
31
 $4,950
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,950
7
8
9
10
11
12
13
$4,950
14
15
16
17
18
19
20
$4,950
21
22
23
24
25
26
27
$4,950
28
29
30
 $4,950
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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ROBIH

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Property Details
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:
$10 - $4,900
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$1,950
8
9
10
11
12
13
14
$1,950
15
16
17
18
19
20
21
$2,050
22
23
24
25
26
27
28
$3,350
29
30
 $4,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
6
7
8
9
10
11
12
$4,500
13
14
15
16
17
18
19
$4,500
20
21
22
23
24
25
26
$4,500
27
28
29
30
31
 $4,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,500
3
4
5
6
7
8
9
$5,100
10
11
12
13
14
15
16
$5,100
17
18
19
20
21
22
23
$5,100
24
25
26
27
28
29
30
$4,900
31
 $2,550
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,550
7
8
9
10
11
12
13
$2,550
14
15
16
17
18
19
20
$1,950
21
22
23
24
25
26
27
$1,950
28
29
30
 $1,950
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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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:
$10 - $4,900
June 2025
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
 $4,700
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,700
6
7
8
9
10
11
12
$4,700
13
14
15
16
17
18
19
$4,700
20
21
22
23
24
25
26
$4,700
27
28
29
30
31
 $4,900
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,900
3
4
5
6
7
8
9
$4,900
10
11
12
13
14
15
16
$4,900
17
18
19
20
21
22
23
$4,900
24
25
26
27
28
29
30
$4,900
31
 
September 2025
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: 
$325 per week
Tax: State & Local: 
11.7

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