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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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 - $7,000
June 2026
SuMoTuWeThFrSaWeek
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$4,300
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$4,300
14
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$4,300
21
22
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$4,500
28
29
30
 $5,000
July 2026
SuMoTuWeThFrSaWeek
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2
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$5,000
5
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$5,000
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$6,000
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$6,000
26
27
28
29
30
31
 $6,000
August 2026
SuMoTuWeThFrSaWeek
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$6,000
2
3
4
5
6
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$7,000
9
10
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$7,000
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$7,000
23
24
25
26
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28
29
$5,500
30
31
 $5,000
September 2026
SuMoTuWeThFrSaWeek
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2
3
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$5,000
6
7
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$4,000
13
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$4,000
20
21
22
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24
25
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$4,000
27
28
29
30
 $3,500
Clean Fee: 
$575
Tax: State & Local: 
11.7

Owner reduced rates for available weeks in June, July & August - see calendar for adjusted rates

 

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HOL14

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Property Details
Gorgeous Waterfront Home on the Lagoon Oak Bluffs, Kayak, Swim, Enjoy the Sunsets, 4 bedrooms 4.5 Baths

Stunning Waterfront home nestled just in the outskirts of Oak Bluffs, 1 mile from town center and Oak Bluffs beaches. This home offers 150 feet of private lagoon beach perfect...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$5,000 - $7,000
June 2026
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July 2026
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August 2026
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September 2026
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Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
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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:
$3,100 - $6,800
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,800
7
8
9
10
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13
$3,800
14
15
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18
19
20
$3,800
21
22
23
24
25
26
27
$5,500
28
29
30
 $6,300
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,300
5
6
7
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10
11
$6,300
12
13
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18
$6,300
19
20
21
22
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24
25
$6,300
26
27
28
29
30
31
 $6,800
August 2026
SuMoTuWeThFrSaWeek
 1
$6,800
2
3
4
5
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$6,800
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$6,800
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$6,800
23
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25
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29
$6,800
30
31
 $5,820
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,820
6
7
8
9
10
11
12
$3,800
13
14
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19
$3,800
20
21
22
23
24
25
26
$3,800
27
28
29
30
 $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:
$3,500 - $6,600
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,500
7
8
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$5,500
14
15
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19
20
$5,500
21
22
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25
26
27
$5,500
28
29
30
 $6,600
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,600
5
6
7
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$6,600
12
13
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$6,600
19
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21
22
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24
25
$6,600
26
27
28
29
30
31
 $6,600
August 2026
SuMoTuWeThFrSaWeek
 1
$6,600
2
3
4
5
6
7
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$6,600
9
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$6,600
16
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21
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$6,600
23
24
25
26
27
28
29
$6,600
30
31
 $5,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500
6
7
8
9
10
11
12
$5,500
13
14
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18
19
$5,500
20
21
22
23
24
25
26
$5,500
27
28
29
30
 $3,500
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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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:
$4,000 - $6,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
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12
13
$4,200
14
15
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18
19
20
$4,200
21
22
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26
27
$4,200
28
29
30
 $5,200
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,200
5
6
7
8
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10
11
$5,200
12
13
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$5,500
19
20
21
22
23
24
25
$5,500
26
27
28
29
30
31
 $6,000
August 2026
SuMoTuWeThFrSaWeek
 1
$6,000
2
3
4
5
6
7
8
$6,500
9
10
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12
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14
15
$6,500
16
17
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21
22
$6,500
23
24
25
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28
29
$6,000
30
31
 $5,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
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$5,000
6
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$5,000
13
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$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
 $4,000
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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VANA2

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Property Details
Charming , Modern In-Town Oak Bluffs Vacation Home. Walk to Town, Parks, Beach. 4 Bedrooms, Sleeps 8, 3 Baths

This charming Oak Bluffs home is tucked away in a peaceful neighborhood, yet conveniently located just a 10-minute walk to the heart of town, the harbor, and the beach. Meticulously...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,500 - $6,500
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSa
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August 2026
SuMoTuWeThFrSaWeek
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$8,500
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$8,500
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$8,500
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$6,500
30
31
 
September 2026
SuMoTuWeThFrSa
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27
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29
30
 
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, 3 bedrooms, 3 Baths, Sleeps, 6 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: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$3,750 - $6,350
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,750
7
8
9
10
11
12
13
$3,750
14
15
16
17
18
19
20
$4,350
21
22
23
24
25
26
27
$4,600
28
29
30
 $5,400
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,400
5
6
7
8
9
10
11
$5,400
12
13
14
15
16
17
18
$5,600
19
20
21
22
23
24
25
$5,600
26
27
28
29
30
31
 $5,600
August 2026
SuMoTuWeThFrSaWeek
 1
$5,600
2
3
4
5
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7
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$6,850
9
10
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12
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14
15
$6,850
16
17
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19
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21
22
$6,850
23
24
25
26
27
28
29
$6,350
30
31
 $3,750
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,750
6
7
8
9
10
11
12
$3,750
13
14
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18
19
$3,750
20
21
22
23
24
25
26
$3,750
27
28
29
30
 $3,750
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:
$5,050 - $6,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,300
7
8
9
10
11
12
13
$5,300
14
15
16
17
18
19
20
$5,300
21
22
23
24
25
26
27
$5,400
28
29
30
 $6,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,000
5
6
7
8
9
10
11
$6,000
12
13
14
15
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17
18
$6,000
19
20
21
22
23
24
25
$6,000
26
27
28
29
30
31
 $6,000
August 2026
SuMoTuWeThFrSaWeek
 1
$6,000
2
3
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5
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7
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$6,000
9
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$6,000
16
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$6,000
23
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29
$6,000
30
31
 $6,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,000
6
7
8
9
10
11
12
$5,100
13
14
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$5,100
20
21
22
23
24
25
26
$5,100
27
28
29
30
 $5,100
Clean Fee: 
$350 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 - $6,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$4,000
14
15
16
17
18
19
20
$4,000
21
22
23
24
25
26
27
$4,000
28
29
30
 $5,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,000
5
6
7
8
9
10
11
$5,000
12
13
14
15
16
17
18
$5,000
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
31
 $5,500
August 2026
SuMoTuWeThFrSaWeek
 1
$5,500
2
3
4
5
6
7
8
$6,000
9
10
11
12
13
14
15
$5,500
16
17
18
19
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21
22
$6,000
23
24
25
26
27
28
29
$6,000
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
$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
 $3,000
Clean Fee: 
$380 per week
Tax: State & Local: 
11.7
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CLARO

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Property Details
Contemporary Farmhouse Design, Multiple Living Areas, Screened Porch & Farmers Porch, Deck, Lovely Yard Area, Bike or Walk to Oak Bluffs Center.

Situated just on the outskirts of Oak Bluffs, this lovely vacation home offers renters modern styling with multiple living spaces and all the conveniences renters look for in a vacation home....Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$2,800 - $5,900
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,300
7
8
9
10
11
12
13
$3,300
14
15
16
17
18
19
20
$3,600
21
22
23
24
25
26
27
$4,300
28
29
30
 $5,300
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,300
5
6
7
8
9
10
11
$5,300
12
13
14
15
16
17
18
$5,300
19
20
21
22
23
24
25
$5,300
26
27
28
29
30
31
 $5,900
August 2026
SuMoTuWeThFrSaWeek
 1
$5,900
2
3
4
5
6
7
8
$6,100
9
10
11
12
13
14
15
$6,100
16
17
18
19
20
21
22
$5,900
23
24
25
26
27
28
29
$5,900
30
31
 $3,600
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,600
6
7
8
9
10
11
12
$3,600
13
14
15
16
17
18
19
$3,100
20
21
22
23
24
25
26
$3,100
27
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

New Bedrooms 3 & 4, in the lower level, and bath are not available in 2025 for the weeks 7/5 & 8/23 and September.  Occupancy limit is 6, 2 Bedrooms 1st and 2nd Level. Sleep sofa and a day bed in the 2nd level family room. Rates listed reflect this arrangement for 2025.  Inquire with Agent for details. 

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ROBIH

(0)Inquire/Share
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:
$2,100 - $5,600
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,150
7
8
9
10
11
12
13
$2,150
14
15
16
17
18
19
20
$2,550
21
22
23
24
25
26
27
$3,500
28
29
30
 $3,800
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,800
5
6
7
8
9
10
11
$3,900
12
13
14
15
16
17
18
$4,600
19
20
21
22
23
24
25
$4,600
26
27
28
29
30
31
 $5,600
August 2026
SuMoTuWeThFrSaWeek
 1
$5,600
2
3
4
5
6
7
8
$5,600
9
10
11
12
13
14
15
$5,600
16
17
18
19
20
21
22
$5,600
23
24
25
26
27
28
29
$3,900
30
31
 $2,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,500
6
7
8
9
10
11
12
$2,500
13
14
15
16
17
18
19
$2,100
20
21
22
23
24
25
26
$2,100
27
28
29
30
 $2,100
Clean Fee: 
$240 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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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 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,500
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
 $5,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,500
5
6
7
8
9
10
11
$5,500
12
13
14
15
16
17
18
$5,000
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
31
 $5,000
August 2026
SuMoTuWeThFrSaWeek
 1
$5,000
2
3
4
5
6
7
8
$7,500
9
10
11
12
13
14
15
$7,500
16
17
18
19
20
21
22
$7,500
23
24
25
26
27
28
29
$5,500
30
31
 $5,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
8
9
10
11
12
$3,000
13
14
15
16
17
18
19
$3,000
20
21
22
23
24
25
26
$2,000
27
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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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 - $5,300
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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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 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
$4,000
21
22
23
24
25
26
27
$4,720
28
29
30
 $5,250
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,250
5
6
7
8
9
10
11
$5,250
12
13
14
15
16
17
18
$5,250
19
20
21
22
23
24
25
$5,250
26
27
28
29
30
31
 $5,770
August 2026
SuMoTuWeThFrSaWeek
 1
$5,770
2
3
4
5
6
7
8
$5,770
9
10
11
12
13
14
15
$5,770
16
17
18
19
20
21
22
$5,770
23
24
25
26
27
28
29
$4,720
30
31
 $3,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
6
7
8
9
10
11
12
$3,000
13
14
15
16
17
18
19
$3,000
20
21
22
23
24
25
26
$2,500
27
28
29
30
 $2,000
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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ROCHA

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Property Details
Bridle Path House, Quiet Lovely Neighborhood, Porch and Deck Areas, Large Yard, Central Location to all 3 Down Island Towns and Beaches

Lovely 3 bedroom 3 bath home sleeps 8, bordered by a large landscaped yard. The exterior features a shady wrap-around porch with rockers, a perfect place to relax, read a book,  and enjoy...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$5,100 - $5,100
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
$5,100
14
15
16
17
18
19
20
21
22
23
24
25
26
27
$5,900
28
29
30
 $5,900
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,900
5
6
7
8
9
10
11
$5,900
12
13
14
15
16
17
18
$5,900
19
20
21
22
23
24
25
$5,900
26
27
28
29
30
31
 $5,900
August 2026
SuMoTuWeThFrSaWeek
 1
$5,900
2
3
4
5
6
7
8
$6,500
9
10
11
12
13
14
15
$6,500
16
17
18
19
20
21
22
$6,500
23
24
25
26
27
28
29
$6,500
30
31
 
September 2026
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: 
$300 per week
Tax: State & Local: 
11.7

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