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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 $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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30
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 $5,500
August 2026
SuMoTuWeThFrSaWeek
 1
$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
27
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29
30
 $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:
$3,500 - $5,000
June 2026
SuMoTuWeThFrSaWeek
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$4,000
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29
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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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27
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30
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 $5,500
August 2026
SuMoTuWeThFrSaWeek
 1
$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
30
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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
27
28
29
30
 $3,500
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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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
28
29
30
 
July 2026
SuMoTuWeThFrSaWeek
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 $4,950
August 2026
SuMoTuWeThFrSaWeek
 1
$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
30
31
 $4,000
September 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
27
28
29
30
 $4,000
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 2026
SuMoTuWeThFrSaWeek
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27
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29
30
 $4,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
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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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27
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30
31
 $4,900
August 2026
SuMoTuWeThFrSaWeek
 1
$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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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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$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
 1
$4,700
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$4,700
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$4,700
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 $4,700
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$4,700
6
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$4,100
13
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$3,900
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26
$3,300
27
28
29
30
 $2,700
Clean Fee: 
$260 per week
Tax: State & Local: 
11.7
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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:
$4,500 - $4,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
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7
8
9
10
11
12
13
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20
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$4,720
28
29
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 $4,900
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$4,900
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$5,000
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$5,000
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$5,000
26
27
28
29
30
31
 $5,100
August 2026
SuMoTuWeThFrSaWeek
 1
$5,100
2
3
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$5,100
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$5,100
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$5,100
23
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28
29
$5,100
30
31
 $4,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$4,500
6
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$4,500
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$4,500
20
21
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$4,500
27
28
29
30
 $4,500
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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KNOXA

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Property Details
Modern Cottage, Recently Updated! Walk to Oak Bluffs Harbor and Town Center, 15 min walk

Walk to Oak Bluffs town center, ferry, or Inkwell Beach from this beach-chic recently renovated, adorable cottage! 

Upon entering you are greeted with an open floor plan in the living, kitchen,...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$3,600 - $4,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
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7
8
9
10
11
12
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20
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$3,600
28
29
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 $4,200
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,200
5
6
7
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11
$4,100
12
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$4,200
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$4,100
26
27
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30
31
 $4,500
August 2026
SuMoTuWeThFrSaWeek
 1
$4,500
2
3
4
5
6
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$6,000
9
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$9,950
16
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$9,950
23
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$4,500
30
31
 $4,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,500
6
7
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10
11
12
$3,850
13
14
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$3,600
20
21
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23
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25
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$3,600
27
28
29
30
 $3,600
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7

Ferry Ticket available for purchase  8/15 -8/22  Please inquire for times of travel!

 

 

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CURRM

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Property Details
Outstanding Designer Home, 15 Min Walk to Oak Bluffs Center, 4 Bedrooms each en suite with TV, Occupancy Limit 9

Stylish Dreamy Home on Dreamer's Way, less than a mile from the town center and beach area! The owners have left nothing out in the way of design and comfort in...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
4
Baths: 
4
Price Range:
$3,500 - $4,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
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7
8
9
10
11
12
13
14
15
16
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20
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25
26
27
$7,900
28
29
30
 $8,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,700
5
6
7
8
9
10
11
$8,700
12
13
14
15
16
17
18
$8,900
19
20
21
22
23
24
25
$9,200
26
27
28
29
30
31
 $9,400
August 2026
SuMoTuWeThFrSaWeek
 1
$9,400
2
3
4
5
6
7
8
$10,700
9
10
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12
13
14
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$11,200
16
17
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22
$10,700
23
24
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28
29
$9,500
30
31
 $8,200
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,200
6
7
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9
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11
12
$6,600
13
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$5,600
20
21
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25
26
$4,600
27
28
29
30
 $4,300
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Owner ACCEPTS 3 NIGHT MINIMUM STAYS, MEMORIAL DAY WEEKEND TO JUNE 16TH, AND SEPT 7TH TO THE END OF OCTOBER.

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HANRJ

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Property Details
Spacious Oak Bluffs Contemporary Home, 4 Bedrooms & 4 Baths, Quiet Private Location in Bayes Hill Community of Homes

Privately situated on the outskirts of Oak Bluffs, yet centrally located to towns and beaches. The home features a large patio area with outdoor dining and grill area and a spacious...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$3,500 - $4,500
June 2026
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
$3,800
28
29
30
 $4,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,500
5
6
7
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10
11
$4,500
12
13
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$4,500
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25
$4,500
26
27
28
29
30
31
 $6,000
August 2026
SuMoTuWeThFrSaWeek
 1
$6,000
2
3
4
5
6
7
8
$7,000
9
10
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13
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$7,000
16
17
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21
22
$7,000
23
24
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27
28
29
$5,500
30
31
 $4,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
6
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12
$4,000
13
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$4,000
20
21
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23
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25
26
$4,000
27
28
29
30
 $3,500
Clean Fee: 
$575
Tax: State & Local: 
11.7

Rates reduced for available weeks June - September - see calendar for adjusted rates

 

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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
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7
8
9
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11
12
13
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20
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27
$3,460
28
29
30
 $4,160
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,160
5
6
7
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9
10
11
$4,160
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$4,160
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25
$4,160
26
27
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30
31
 $4,160
August 2026
SuMoTuWeThFrSaWeek
 1
$4,160
2
3
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$4,160
9
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$4,160
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$4,160
23
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28
29
$4,160
30
31
 $4,160
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,160
6
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12
$4,160
13
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19
$4,160
20
21
22
23
24
25
26
$4,160
27
28
29
30
 $4,160
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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ST203

Inquire
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
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
$4,300
28
29
30
 $4,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,500
5
6
7
8
9
10
11
$4,700
12
13
14
15
16
17
18
$4,700
19
20
21
22
23
24
25
$4,700
26
27
28
29
30
31
 $5,000
August 2026
SuMoTuWeThFrSaWeek
 1
$5,000
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
 $5,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
8
9
10
11
12
$4,500
13
14
15
16
17
18
19
$4,100
20
21
22
23
24
25
26
$4,100
27
28
29
30
 $4,100
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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ROLAJ

Inquire
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 - $4,000
June 2026
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July 2026
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August 2026
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September 2026
SuMoTuWeThFrSaWeek
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$4,500
27
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 $4,000
Clean Fee: 
$250 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
7
8
9
10
11
12
13
14
15
16
17
18
19
20
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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PETEV

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

MVVR Exclusive! Spacious, traditional waterfront Cape Cod style home tucked away on the shores of Sengekontacket Lagoon in a community of homes - featuring gorgeous views, mini-split AC units in main living areas,...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
4
Baths: 
2
Price Range:
$2,460 - $3,900
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
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12
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19
20
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
 
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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KLEIB

Inquire
Property Details
Lagoon Waterfront & Beachfront, Spectacular Water views, Room A/C, WIFI

Adorable waterfront & beachfront cottage.   Immaculately maintained, lots of summer charm, fantastic views of the Vineyard Sound and Lagoon from the large patio area. Stairs lead directly to a...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$3,640 - $3,640
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
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12
13
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20
21
22
23
24
25
26
27
$3,640
28
29
30
 $3,980
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,980
5
6
7
8
9
10
11
$4,070
12
13
14
15
16
17
18
$4,090
19
20
21
22
23
24
25
$4,200
26
27
28
29
30
31
 $4,300
August 2026
SuMoTuWeThFrSaWeek
 1
$4,300
2
3
4
5
6
7
8
$4,390
9
10
11
12
13
14
15
$4,390
16
17
18
19
20
21
22
$4,200
23
24
25
26
27
28
29
$3,850
30
31
 $3,300
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,300
6
7
8
9
10
11
12
$2,820
13
14
15
16
17
18
19
$2,560
20
21
22
23
24
25
26
$2,460
27
28
29
30
 $2,350
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7

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