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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"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 - $5,000
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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$4,000
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 $5,000
July 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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 $5,500
August 2026
SuMoTuWeThFrSaWeek
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$5,500
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$7,500
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$7,500
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$7,500
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$7,500
30
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 $5,000
September 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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29
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 $5,000
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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DUREJ

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Property Details

This luxuriously updated tri-level condo retreat at Quail Run in the community of homes known as Sengekontacket, has been transformed, bringing a fresh, coastal feel to every corner. The end...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
1
Price Range:
$70 - $5,000
June 2026
SuMoTuWeThFrSaWeek
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$3,500
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$3,500
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$3,500
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$4,000
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 $5,500
July 2026
SuMoTuWeThFrSaWeek
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$5,500
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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 2026
SuMoTuWeThFrSaWeek
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$5,500
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$6,000
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$6,000
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$5,750
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$5,000
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 $4,000
September 2026
SuMoTuWeThFrSaWeek
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$4,000
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$3,500
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$3,500
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 $3,500
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
Add Favorite
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TOTHG

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Property Details

Note: Older style TVs seen in photos have been replaced. 

This bright and classic summer cottage is ideally located just one mile from Oak Bluffs town center and all the...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$4,000 - $4,950
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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$4,000
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July 2026
SuMoTuWeThFrSaWeek
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 $4,950
August 2026
SuMoTuWeThFrSaWeek
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$4,950
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$4,950
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$4,950
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 $4,000
September 2026
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$4,000
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$4,000
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$4,000
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 $4,000
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
Add Favorite
 
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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
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 2026
SuMoTuWeThFrSaWeek
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$4,900
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Clean Fee: 
$350 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
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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 $4,700
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
 1
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$4,700
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$4,100
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$3,900
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$3,300
27
28
29
30
 $2,700
Clean Fee: 
$260 per week
Tax: State & Local: 
11.7
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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 - $4,600
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,300
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$4,600
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30
 
July 2026
SuMoTuWeThFrSa
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August 2026
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September 2026
SuMoTuWeThFrSaWeek
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$4,500
27
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29
30
 $4,000
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
Add Favorite
 
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ST304

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Property Details
Sea View Condominium, Water View, Walk to Town & Beach-Across the Street

Sea View Condominium with a breathtaking view of Nantucket Sound from almost every room. Just steps from the beach.Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$70 - $4,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,200
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$4,200
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$4,550
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27
$4,720
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29
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 $4,900
July 2026
SuMoTuWeThFrSaWeek
 1
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$4,900
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$5,000
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$5,000
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$5,000
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 $5,100
August 2026
SuMoTuWeThFrSaWeek
 1
$5,100
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$5,100
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$5,100
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$5,100
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$5,100
30
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 $4,500
September 2026
SuMoTuWeThFrSaWeek
 1
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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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29
30
 $4,500
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
Add Favorite
 
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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:
$2,600 - $4,200
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,400
7
8
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13
$3,050
14
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$3,050
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22
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27
$3,200
28
29
30
 $4,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,000
5
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$4,000
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$4,200
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$4,200
26
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 $4,500
August 2026
SuMoTuWeThFrSaWeek
 1
$4,500
2
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$4,500
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$4,500
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$4,500
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$3,400
30
31
 $2,600
September 2026
SuMoTuWeThFrSaWeek
 1
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$2,600
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$2,600
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$2,600
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$2,600
27
28
29
30
 $2,600
Clean Fee: 
$375 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:
$3,000 - $4,200
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,000
7
8
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13
$3,000
14
15
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$3,600
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27
$4,200
28
29
30
 
July 2026
SuMoTuWeThFrSa
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August 2026
SuMoTuWeThFrSaWeek
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$5,000
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$5,500
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$5,700
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$4,000
30
31
 $4,200
September 2026
SuMoTuWeThFrSaWeek
 1
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$4,200
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$3,000
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$3,000
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$3,000
27
28
29
30
 $2,300
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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SACHE

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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:
$3,460 - $4,160
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$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
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 $4,160
July 2026
SuMoTuWeThFrSaWeek
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$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
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
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 $4,160
September 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
27
28
29
30
 $4,160
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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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: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$4,100 - $4,100
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,300
7
8
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10
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13
$4,300
14
15
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20
$4,300
21
22
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27
$4,300
28
29
30
 $4,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,500
5
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$4,700
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$4,700
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25
$4,700
26
27
28
29
30
31
 $5,000
August 2026
SuMoTuWeThFrSaWeek
 1
$5,000
2
3
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$5,200
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$5,200
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$5,200
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$5,200
30
31
 $5,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
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12
$4,500
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$4,100
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21
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25
26
$4,100
27
28
29
30
 $4,100
Clean Fee: 
$275 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, 7 MINUTE DRIVE TO THE CENTER OF OAK BLUFFS AND INKWELL BEACH

Experience the best of Island living—peaceful residential surroundings, the vibrant shops and attractions of the three Down Island towns (Oak Bluffs, Edgartown, and Vineyard Haven), and quick access to public...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$3,500 - $4,100
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
$3,500
28
29
30
 $4,100
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,100
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
$5,200
9
10
11
12
13
14
15
$5,200
16
17
18
19
20
21
22
$5,200
23
24
25
26
27
28
29
$5,200
30
31
 $3,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
6
7
8
9
10
11
12
$3,500
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: 
$450 per week
Tax: State & Local: 
11.7

 

 

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CAH48

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Property Details
Classic Lovely Vineyard Cottage, Approximately 1.5 Miles to Oak Bluffs Center 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
 $3,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,000
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

Owner will rent off weekend dates, with a 7-night minimum, to accommodate the need for auto ticket reservations.  

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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:
$3,000 - $3,800
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,000
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
$3,800
28
29
30
 $4,600
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,600
5
6
7
8
9
10
11
$4,600
12
13
14
15
16
17
18
$4,600
19
20
21
22
23
24
25
$4,600
26
27
28
29
30
31
 $5,250
August 2026
SuMoTuWeThFrSaWeek
 1
$5,250
2
3
4
5
6
7
8
$5,300
9
10
11
12
13
14
15
$5,500
16
17
18
19
20
21
22
$5,300
23
24
25
26
27
28
29
$4,300
30
31
 $3,200
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,200
6
7
8
9
10
11
12
$3,200
13
14
15
16
17
18
19
$3,000
20
21
22
23
24
25
26
$3,000
27
28
29
30
 $3,000
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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PETEV

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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:
$3,600 - $3,700
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
 $3,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,700
5
6
7
8
9
10
11
$4,100
12
13
14
15
16
17
18
$3,700
19
20
21
22
23
24
25
$3,700
26
27
28
29
30
31
 $3,700
August 2026
SuMoTuWeThFrSaWeek
 1
$3,700
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

Owner just reduced rates for available weeks in July - see calendar for adjusted rates

 

Owner will rent weekday to weekday the middle two weeks of July with a 7 night minimum to accommodate the need for auto ferry tickets if none available the weekend dates. 

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