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Your connection to all Martha's Vineyard Real Estate and Vacation Rentals
508-693-7832
Karen M. Overtoom Logo
508-693-7832


Martha's Vineyard Vacation Rentals in Oak Bluffs








Oak Bluffs Victorian


"Three plus bedroom close to town and East Chop Jetty beach!"

1900 Oak Bluffs Victorian. A very short distance to Nancy’s restaurant/downtown OB and to Jetty beach. The house was purchased empty in 2018 so all furnishings are new and the house is freshly painted. On the second floor, there are 3 bedrooms and a full bathroom, which connects to hall and prima...Read the full description.

JUNE 2025
S M T W T F S Cost
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7
CALL
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CALL
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CALL
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CALL
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          CALL
               
JULY 2025
S M T W T F S Cost
   
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5
CALL
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CALL
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CALL
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CALL
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31
    CALL
               
AUGUST 2025
S M T W T F S Cost
         
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2
CALL
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4
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7
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9
CALL
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16
$5,000.
17
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22
23
$5,000.
24
25
26
27
28
29
30
CALL
31
            CALL
SEPTEMBER 2025
S M T W T F S Cost
 
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CALL
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CALL
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        CALL
               

Wonderful Oak Bluffs Condo With Pool


"Stunning 3 Bedroom condo with pool"

Welcome to "Shangrila" A beautiful townhouse condominium end unit with magnificent views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great livin...Read the full description.

JUNE 2025
S M T W T F S Cost
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5
6
7
$4,395.
8
9
10
11
12
13
14
$4,675.
15
16
17
18
19
20
21
$4,950.
22
23
24
25
26
27
28
$5,225.
29
30
          $5,995.
               
JULY 2025
S M T W T F S Cost
   
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2
3
4
5
$5,995.
6
7
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10
11
12
$5,495.
13
14
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18
19
$5,745.
20
21
22
23
24
25
26
$5,745.
27
28
29
30
31
    $5,995.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$5,995.
3
4
5
6
7
8
9
$5,995.
10
11
12
13
14
15
16
$5,745.
17
18
19
20
21
22
23
$5,495.
24
25
26
27
28
29
30
$5,245.
31
            $5,245.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
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5
6
$5,245.
7
8
9
10
11
12
13
$4,895.
14
15
16
17
18
19
20
$4,125.
21
22
23
24
25
26
27
$4,125.
28
29
30
        $3,855.
               

Victorian Cottage Overlooking Nantucket Sound


"Victorian Cottage in the Heart of Oak Bluffs"

Victorian Cottage located on Ocean Park in the heart of Oak Bluffs with fully equipped and updated kitchen, five bedrooms and three baths, cozy living spaces and multiple amenities will accommodate your family and friends. Smell the sea air and watch the waves break from your front porch. This char...Read the full description.

JUNE 2025
S M T W T F S Cost
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5
6
7
CALL
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9
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CALL
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CALL
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23
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27
28
CALL
29
30
          CALL
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
CALL
6
7
8
9
10
11
12
CALL
13
14
15
16
17
18
19
CALL
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21
22
23
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CALL
27
28
29
30
31
    $7,300.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$7,300.
3
4
5
6
7
8
9
$7,300.
10
11
12
13
14
15
16
$7,300.
17
18
19
20
21
22
23
$7,300.
24
25
26
27
28
29
30
$7,300.
31
            CALL
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
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5
6
CALL
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8
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CALL
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CALL
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        CALL
               

Central Location for Your Vacation


"Nicely Furnished Two Bedroom in Peaceful Neighborhood"

This bright contemporary home is in the perfect central location to downtown of Vineyard Haven, Oak Bluffs and Edgartown. Explore and enjoy the vibrant and colorful life of towns, nature trails, beaches and peace of indoors. Two bedroom raised ranch with plenty of deck space at the end of a woode...Read the full description.

JUNE 2025
S M T W T F S Cost
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7
$2,500.
8
9
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13
14
$2,500.
15
16
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18
19
20
21
$2,500.
22
23
24
25
26
27
28
$2,800.
29
30
          $2,800.
               
JULY 2025
S M T W T F S Cost
   
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2
3
4
5
$2,800.
6
7
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9
10
11
12
$2,800.
13
14
15
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18
19
$2,800.
20
21
22
23
24
25
26
$2,800.
27
28
29
30
31
    $2,800.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$2,800.
3
4
5
6
7
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9
$2,800.
10
11
12
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14
15
16
$2,800.
17
18
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20
21
22
23
$2,800.
24
25
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27
28
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30
$2,700.
31
            $2,700.
SEPTEMBER 2025
S M T W T F S Cost
 
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$2,700.
7
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13
$2,700.
14
15
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19
20
$2,100.
21
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27
$2,100.
28
29
30
        $2,100.