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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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 2026
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 $4,500
July 2026
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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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 $5,000
August 2026
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
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 $4,000
September 2026
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$4,000
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Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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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 2026
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Clean Fee: 
$400 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 2026
SuMoTuWeThFrSaWeek
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 $4,700
July 2026
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$4,700
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$4,700
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 $4,900
August 2026
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
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September 2026
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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:
$2,300 - $4,900
June 2026
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$3,000
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$3,600
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$4,200
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 $4,200
July 2026
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$4,200
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 $4,200
August 2026
SuMoTuWeThFrSaWeek
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$4,200
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$5,000
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$5,500
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$5,700
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$4,000
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 $4,200
September 2026
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$3,000
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 $2,300
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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GRATD

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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:
$2,000 - $4,700
June 2026
SuMoTuWeThFrSaWeek
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$3,900
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$3,900
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$4,000
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$4,300
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 $4,700
July 2026
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$4,700
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$4,700
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 $4,700
August 2026
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
September 2026
SuMoTuWeThFrSaWeek
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$4,700
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$4,100
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$3,900
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$3,300
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 $2,700
Clean Fee: 
$260 per week
Tax: State & Local: 
11.7
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KEANM

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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:
$2,500 - $4,700
June 2026
SuMoTuWeThFrSaWeek
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$3,000
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 $4,600
July 2026
SuMoTuWeThFrSaWeek
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$4,600
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$4,600
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 $4,600
August 2026
SuMoTuWeThFrSaWeek
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$4,600
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$4,700
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$4,700
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$4,700
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 $4,700
September 2026
SuMoTuWeThFrSaWeek
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$4,700
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$3,000
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$3,000
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30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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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 - $4,500
June 2026
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$4,000
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$3,800
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 $3,800
July 2026
SuMoTuWeThFrSaWeek
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$3,800
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$3,800
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$4,100
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$4,100
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 $4,500
August 2026
SuMoTuWeThFrSaWeek
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$4,500
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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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 $4,500
September 2026
SuMoTuWeThFrSaWeek
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$4,500
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$3,900
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$3,900
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$3,900
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 $3,900
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

 

 

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DONOP

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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 - $4,200
June 2026
SuMoTuWeThFrSaWeek
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$2,400
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$3,050
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$3,050
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$3,200
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 $4,000
July 2026
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$4,200
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$4,200
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 $4,500
August 2026
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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$3,400
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 $2,600
September 2026
SuMoTuWeThFrSaWeek
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$2,600
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$2,600
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$2,600
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$2,600
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29
30
 $2,600
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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ALLER

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Property Details
Oak Bluffs 4 Bedroom Home, Walk to Town & Beach!

10-minute walk to Oak Bluffs center and beach area from this lovely modern vacation home.  Enjoy all that the summer community of Oak Bluffs has to offer with quaint shops,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,200 - $4,200
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$3,700
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$3,700
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$3,700
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$3,900
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29
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 $5,250
July 2026
SuMoTuWeThFrSaWeek
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2
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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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 $5,250
August 2026
SuMoTuWeThFrSaWeek
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$5,250
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$6,000
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$6,000
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$6,000
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$5,750
30
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 $4,500
September 2026
SuMoTuWeThFrSaWeek
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$4,500
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$4,200
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$4,200
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$4,200
27
28
29
30
 $4,200
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
Add Favorite
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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 - $4,200
June 2026
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Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
Add Favorite
 
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SACHE

(0)Inquire/Share
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:
$3,000 - $4,160
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
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5
6
$3,460
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$3,460
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$3,460
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$3,460
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29
30
 $4,160
July 2026
SuMoTuWeThFrSaWeek
 1
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$4,160
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$4,160
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$4,160
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$4,160
26
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30
31
 $4,160
August 2026
SuMoTuWeThFrSaWeek
 1
$4,160
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$4,160
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$4,160
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$4,160
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$4,160
30
31
 $4,160
September 2026
SuMoTuWeThFrSaWeek
 1
2
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5
$4,160
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$4,160
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$4,160
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25
26
$4,160
27
28
29
30
 $4,160
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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PETEV

(0)Inquire/Share
Property Details
Lovely Waterfront Home, Oak Bluffs, Gorgeous Water Views, Association Tennis Courts, AC, Wi-fi, Bike Paths Nearby

Note: Pricing for this waterfront home takes into account that this is an older-style home. Please note that baths and kitchen have not been updated

MVVR Exclusive! Spacious, traditional waterfront Cape Cod style home...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
4
Baths: 
2
Price Range:
$2,460 - $4,100
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,600
7
8
9
10
11
12
13
$3,600
14
15
16
17
18
19
20
$3,600
21
22
23
24
25
26
27
28
29
30
 
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
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
31
 $4,100
August 2026
SuMoTuWeThFrSaWeek
 1
$4,100
2
3
4
5
6
7
8
$4,100
9
10
11
12
13
14
15
$4,100
16
17
18
19
20
21
22
$4,100
23
24
25
26
27
28
29
$3,910
30
31
 $3,660
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,660
6
7
8
9
10
11
12
$3,660
13
14
15
16
17
18
19
$3,660
20
21
22
23
24
25
26
$2,460
27
28
29
30
 $2,460
Clean Fee: 
$475 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 - $4,000
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSa
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August 2026
SuMoTuWeThFrSa
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September 2026
SuMoTuWeThFrSa
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12
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14
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22
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24
25
26
27
28
29
30
 
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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MAHAB

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Property Details
Sweet Updated 3 Bedroom Home, Nicely Tucked in Lightly Wooded Area, Central Location, Beaches and Towns just a short Drive!

Lovely reverse contemporary home with a large deck, outdoor dining, and grill area. The upper level of this home features an open kitchen, living, and dining area stylishly furnished.  Nicely equipped kitchen...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
1
Price Range:
$3,500 - $4,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,500
7
8
9
10
11
12
13
$3,500
14
15
16
17
18
19
20
$3,500
21
22
23
24
25
26
27
$4,000
28
29
30
 $4,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,000
5
6
7
8
9
10
11
$4,000
12
13
14
15
16
17
18
$4,000
19
20
21
22
23
24
25
$4,000
26
27
28
29
30
31
 $4,000
August 2026
SuMoTuWeThFrSaWeek
 1
$4,000
2
3
4
5
6
7
8
$4,000
9
10
11
12
13
14
15
$4,000
16
17
18
19
20
21
22
$4,000
23
24
25
26
27
28
29
$4,000
30
31
 $4,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
6
7
8
9
10
11
12
$4,000
13
14
15
16
17
18
19
$3,500
20
21
22
23
24
25
26
$3,500
27
28
29
30
 $3,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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CAH48

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Property Details
Classic Lovely Vineyard Cottage, Pristine Condition, Approximately 1.5 Miles to Town and Beaches. Mature Landscaped Yard, Spacious Deck

The Perfect Cozy Cottage, is pristinely maintained and situated in a quiet neighborhood just on the outskirts of Oak Bluffs.  This spacious 2 bedroom, 2 bath home sleeps 4. The...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,700 - $4,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,700
7
8
9
10
11
12
13
$2,700
14
15
16
17
18
19
20
$2,700
21
22
23
24
25
26
27
$2,700
28
29
30
 $3,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,500
5
6
7
8
9
10
11
$3,500
12
13
14
15
16
17
18
$3,500
19
20
21
22
23
24
25
$3,500
26
27
28
29
30
31
 $4,000
August 2026
SuMoTuWeThFrSaWeek
 1
$4,000
2
3
4
5
6
7
8
$4,000
9
10
11
12
13
14
15
$4,000
16
17
18
19
20
21
22
$4,000
23
24
25
26
27
28
29
$4,000
30
31
 $2,700
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,700
6
7
8
9
10
11
12
$2,700
13
14
15
16
17
18
19
$2,700
20
21
22
23
24
25
26
$2,700
27
28
29
30
 
Clean Fee: 
$300, additional may apply multiple week rentals
Tax: State & Local: 
11.7

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