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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








Charming Beach House - The Perfect Vacation Escape!


"Just Minutes To A Private Sandy Lagoon Beach."

This irresistible home is a very short distance from a deeded, sandy, sheltered beach and only a few minutes drive to the town of Vineyard Haven and the center of Oak Bluffs and all the fun activities that Circuit Avenue has to offer. The casual getaway has wonderful ambiance enhanced by its soarin...Read the full description.

JUNE 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$3,000.
8
9
10
11
12
13
14
$3,000.
15
16
17
18
19
20
21
$3,000.
22
23
24
25
26
27
28
$3,000.
29
30
          $3,200.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$3,200.
6
7
8
9
10
11
12
$3,200.
13
14
15
16
17
18
19
$3,400.
20
21
22
23
24
25
26
$3,400.
27
28
29
30
31
    $3,400.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$3,400.
3
4
5
6
7
8
9
$3,500.
10
11
12
13
14
15
16
$3,500.
17
18
19
20
21
22
23
$3,500.
24
25
26
27
28
29
30
$3,200.
31
            $3,200.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$3,200.
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
        $3,000.
               

Spectacular Waterfront With Deep-Water Dock!


"Brand New Oak Bluffs Rental, Luxury, Waterfront With Deep Water Dock, Mooring, And Private Beach."

This home offers a spacious open floor plan providing a comfortable yet elegant retreat, truly an upscale surprise, perfect for relaxing or entertaining. With an expansive mahogany wraparound deck, sweeping views and a screened-in porch, enjoying the evening sunsets while grilling and dining al fre...Read the full description.

JUNE 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$7,000.
8
9
10
11
12
13
14
$7,000.
15
16
17
18
19
20
21
$7,000.
22
23
24
25
26
27
28
$8,500.
29
30
          $11,000.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$11,000.
6
7
8
9
10
11
12
$11,000.
13
14
15
16
17
18
19
$12,000.
20
21
22
23
24
25
26
$14,600.
27
28
29
30
31
    $14,000.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$14,000.
3
4
5
6
7
8
9
$15,000.
10
11
12
13
14
15
16
$15,000.
17
18
19
20
21
22
23
$16,500.
24
25
26
27
28
29
30
$12,500.
31
            $7,500.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$7,500.
7
8
9
10
11
12
13
$7,500.
14
15
16
17
18
19
20
$7,000.
21
22
23
24
25
26
27
$7,000.
28
29
30
        $7,000.
               

Beautiful Cottage Close to Town


"Renovated and Spacious East Chop Home Close to Everything"

Wonderful, fully redecorated Gingerbread house on East Chop, just minutes from the excitement of Oak Bluffs. There are three bedrooms and two full baths. The interior is clean and crisp, with beach cottage décor and beautiful bamboo floors. Entertainment options include high-speed wifi, Sonos, cable...Read the full description.

JUNE 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$4,200.
8
9
10
11
12
13
14
$4,200.
15
16
17
18
19
20
21
$4,200.
22
23
24
25
26
27
28
$5,500.
29
30
          $5,500.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$5,500.
6
7
8
9
10
11
12
$5,500.
13
14
15
16
17
18
19
$5,500.
20
21
22
23
24
25
26
$5,500.
27
28
29
30
31
    $6,400.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$6,400.
3
4
5
6
7
8
9
$6,400.
10
11
12
13
14
15
16
$6,400.
17
18
19
20
21
22
23
$6,400.
24
25
26
27
28
29
30
$6,250.
31
            $5,250.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$5,250.
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
        $3,500.
               

Beautiful Oak Bluffs Home on Lagoon


"Waterfront with Private Heated Pool"

This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with waterviews over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in dining overlooking the pool. The fi...Read the full description.

JUNE 2025
S M T W T F S Cost
1
2
3
4
5
6
7
CALL
8
9
10
11
12
13
14
CALL
15
16
17
18
19
20
21
CALL
22
23
24
25
26
27
28
CALL
29
30
          $22,000.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$22,000.
6
7
8
9
10
11
12
$22,000.
13
14
15
16
17
18
19
$22,000.
20
21
22
23
24
25
26
$22,000.
27
28
29
30
31
    $22,000.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$22,000.
3
4
5
6
7
8
9
$22,000.
10
11
12
13
14
15
16
$22,000.
17
18
19
20
21
22
23
$22,000.
24
25
26
27
28
29
30
$22,000.
31
            $22,000.
SEPTEMBER 2025
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