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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








Waterview Farms, Prime Bike Trails, Martha's Vineyard!


"Oak Bluffs Rental, Fabulous Waterview Farms Contemporary, Association Beach And Dock."

Located in Waterview Farms, this four bedroom home features a private beach on Sengekontacket Pond, private dock access to Land Bank boat launch and several beautiful trails. The association water front beach is about 1/3 of a mile from the house as the the bird flies. You can also drive your car do...Read the full description.

JUNE 2026
S M T W T F S Cost
 
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
S M T W T F S Cost
     
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
S M T W T F S Cost
           
1
$5,500.
2
3
4
5
6
7
8
$5,500.
9
10
11
12
13
14
15
$5,500.
16
17
18
19
20
21
22
$5,500.
23
24
25
26
27
28
29
$5,500.
30
31
          $5,500.
SEPTEMBER 2026
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
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Call
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Call
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      Call
               

Downtown Oak Bluffs!


"Quintessential Cottage Charm Close to Circuit Ave and Inkwell Beach!"

Newly renovated, Great for Family Gatherings, Corporate Retreats, Central Air & Heat, very close to Circuit Ave and Beach, 5 Bedrooms, 3 full baths, galley kitchen, new appliances, dining room, family room, Flat Screen TV, FREE Wifi, washer & dryer, bay window breakfast nook, Oak and Pine wood floor...Read the full description.

JUNE 2026
S M T W T F S Cost
 
1
2
3
4
5
6
$13,000.
7
8
9
10
11
12
13
$13,000.
14
15
16
17
18
19
20
$13,000.
21
22
23
24
25
26
27
$13,000.
28
29
30
        $13,000.
               
JULY 2026
S M T W T F S Cost
     
1
2
3
4
$13,000.
5
6
7
8
9
10
11
$13,000.
12
13
14
15
16
17
18
$13,000.
19
20
21
22
23
24
25
$13,000.
26
27
28
29
30
31
  $13,000.
               
AUGUST 2026
S M T W T F S Cost
           
1
$13,000.
2
3
4
5
6
7
8
$15,400.
9
10
11
12
13
14
15
$21,000.
16
17
18
19
20
21
22
$21,000.
23
24
25
26
27
28
29
$17,500.
30
31
          $13,000.
SEPTEMBER 2026
S M T W T F S Cost
   
1
2
3
4
5
$13,000.
6
7
8
9
10
11
12
$13,000.
13
14
15
16
17
18
19
$10,500.
20
21
22
23
24
25
26
$10,500.
27
28
29
30
      $10,500.
               

Serene Oak Bluffs Vacation


"Beautifully Appointed Home"

Discover the charm of this classic three-bedroom Cape, perfectly designed for relaxation and island living. The home features a comfortable living room, a cozy den, and a fully equipped kitchen that serves as the heart of the space. Whether you’re preparing a family meal or a quick snack, the kitche...Read the full description.

JUNE 2026
S M T W T F S Cost
 
1
2
3
4
5
6
Call
7
8
9
10
11
12
13
Call
14
15
16
17
18
19
20
Call
21
22
23
24
25
26
27
Call
28
29
30
        Call
               
JULY 2026
S M T W T F S Cost
     
1
2
3
4
Call
5
6
7
8
9
10
11
Call
12
13
14
15
16
17
18
Call
19
20
21
22
23
24
25
Call
26
27
28
29
30
31
  Call
               
AUGUST 2026
S M T W T F S Cost
           
1
Call
2
3
4
5
6
7
8
Call
9
10
11
12
13
14
15
Call
16
17
18
19
20
21
22
Call
23
24
25
26
27
28
29
Call
30
31
          Call
SEPTEMBER 2026
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
20
21
22
23
24
25
26
Call
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28
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30
      Call
               

East Chop Waterfront


"The Boat House"

Located on majestic East Chop and only a mile and a half from both Vineyard Haven and Oak Bluffs, this rustic ocean front cottage offers a unique Martha's Vineyard experience. Whether you relax on the the private beach and watch mesmerizing sunsets, visit the East Chop Lighthouse, or head only a ...Read the full description.

JUNE 2026
S M T W T F S Cost
 
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
        $4,000.
               
JULY 2026
S M T W T F S Cost
     
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
  $4,200.
               
AUGUST 2026
S M T W T F S Cost
           
1
$4,200.
2
3
4
5
6
7
8
$4,500.
9
10
11
12
13
14
15
$4,500.
16
17
18
19
20
21
22
$4,500.
23
24
25
26
27
28
29
$4,500.
30
31
          $4,000.
SEPTEMBER 2026
S M T W T F S Cost
   
1
2
3
4
5
$4,000.
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.