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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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:
$4,600 - $6,000
June 2025
SuMoTuWeThFrSaWeek
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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
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$6,500
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$6,500
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$6,000
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 $6,000
September 2025
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$6,000
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$5,000
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$5,000
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$5,000
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30
 $5,000
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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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:
$2,300 - $5,700
June 2025
SuMoTuWeThFrSaWeek
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 $4,200
July 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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 $4,200
August 2025
SuMoTuWeThFrSaWeek
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$4,200
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$5,000
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$5,700
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$5,000
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$5,000
31
 $4,900
September 2025
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$4,900
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$3,000
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$3,000
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$3,000
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29
30
 $2,300
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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BARNJ

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Property Details
Chic, Meticulously Maintained Cape Style Home. Walk to Oak Bluffs Town Center and Beaches, Tucked on a Large Beautifully Landscaped Lot

Nestled in a beautifully landscaped lot in a serene and private neighborhood, this meticulously maintained cottage in Oak Bluffs, Martha's Vineyard, offers a perfect retreat for rental guests. With chic...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
3
Price Range:
$3,750 - $5,600
June 2025
SuMoTuWeThFrSaWeek
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 $5,000
July 2025
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$5,000
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$5,000
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$5,600
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$5,600
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 $5,600
August 2025
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$5,600
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$6,350
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$6,350
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$6,350
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$6,350
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 $3,750
September 2025
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$3,750
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$3,750
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$3,750
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$3,750
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30
 $3,750
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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HAZAM

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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:
$3,000 - $5,600
June 2025
SuMoTuWeThFrSaWeek
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 $5,000
July 2025
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$5,000
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$5,000
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$5,600
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$5,600
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 $5,600
August 2025
SuMoTuWeThFrSaWeek
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$5,600
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$6,400
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$6,400
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$6,400
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$6,000
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 $4,000
September 2025
SuMoTuWeThFrSaWeek
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$4,000
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$3,750
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$3,750
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$3,750
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29
30
 $3,000
Clean Fee: 
$350
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:
$3,500 - $5,500
June 2025
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July 2025
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$5,500
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August 2025
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 $5,500
September 2025
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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30
 $3,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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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:
$2,500 - $5,500
June 2025
SuMoTuWeThFrSaWeek
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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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31
 $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
31
 $3,200
September 2025
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
28
29
30
 $3,000
Clean Fee: 
$400 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 - $5,500
June 2025
SuMoTuWeThFrSaWeek
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 $5,000
July 2025
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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 $5,500
August 2025
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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$5,500
31
 $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
28
29
30
 $3,000
Clean Fee: 
$350 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:
$2,000 - $5,500
June 2025
SuMoTuWeThFrSaWeek
1
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 $3,500
July 2025
SuMoTuWeThFrSaWeek
 1
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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
2
$3,000
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$5,000
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$5,750
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$5,750
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$5,250
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 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
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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
29
30
 $2,000
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

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

 

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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:
$2,000 - $5,250
June 2025
SuMoTuWeThFrSaWeek
1
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 $5,250
July 2025
SuMoTuWeThFrSaWeek
 1
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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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30
$4,720
31
 $3,500
September 2025
SuMoTuWeThFrSaWeek
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3
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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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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:
$3,500 - $5,200
June 2025
SuMoTuWeThFrSaWeek
1
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 $4,100
July 2025
SuMoTuWeThFrSaWeek
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$4,100
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$4,100
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$4,100
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$4,100
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 $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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30
$4,900
31
 $4,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
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$4,500
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$4,500
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$4,000
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$4,000
28
29
30
 $4,000
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

 

 

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WILCM

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Property Details
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:
$3,800 - $5,000
June 2025
SuMoTuWeThFrSaWeek
1
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 $4,500
July 2025
SuMoTuWeThFrSaWeek
 1
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3
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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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31
 $5,000
August 2025
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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25
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27
28
29
30
$4,500
31
 $3,800
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,800
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8
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13
$3,800
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
Add Favorite
 
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NEWMJ

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Property Details

Newly update mid-century modern beach house set in the private community of homes surrounding Sengekontacket pond. The cozy summer cottage offers indoor and outdoor living at its best with a...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,850 - $4,960
June 2025
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 $6,090
July 2025
SuMoTuWeThFrSaWeek
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$6,090
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$6,090
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$6,090
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$6,090
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 $6,090
August 2025
SuMoTuWeThFrSaWeek
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$6,090
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$6,090
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$6,090
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$6,090
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$6,090
31
 $6,090
September 2025
SuMoTuWeThFrSaWeek
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$6,090
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$4,960
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$3,850
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$3,850
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 $3,850
Clean Fee: 
$400 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:
$3,900 - $4,950
June 2025
SuMoTuWeThFrSaWeek
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 $4,950
July 2025
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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 $4,950
August 2025
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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$4,950
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
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$4,000
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$3,900
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$3,900
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$3,900
28
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30
 
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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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:
$4,700 - $4,900
June 2025
SuMoTuWeThFrSaWeek
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 $4,700
July 2025
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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 $4,900
August 2025
SuMoTuWeThFrSaWeek
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$4,900
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$4,900
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$4,900
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$4,900
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$4,900
31
 
September 2025
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Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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ST203

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Property Details
Seaview Condominium, Waterview, Walk to Town and Beach

Beachfront Condominium with breathtaking views of Nantucket Sound. Just steps to the beach.Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
2
Price Range:
$2,900 - $4,800
June 2025
SuMoTuWeThFrSaWeek
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 $4,600
July 2025
SuMoTuWeThFrSaWeek
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$4,600
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$4,800
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$4,800
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$4,800
27
28
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31
 $5,200
August 2025
SuMoTuWeThFrSaWeek
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2
$5,200
3
4
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$5,300
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$5,300
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$5,600
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$5,300
31
 $3,600
September 2025
SuMoTuWeThFrSaWeek
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$3,600
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$3,300
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$2,900
21
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$2,900
28
29
30
 $2,900
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7

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