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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








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 2026
S M T W T F S Cost
 
1
2
3
4
5
6
$7,000.
7
8
9
10
11
12
13
$7,000.
14
15
16
17
18
19
20
$7,000.
21
22
23
24
25
26
27
$8,500.
28
29
30
        $11,000.
               
JULY 2026
S M T W T F S Cost
     
1
2
3
4
$11,000.
5
6
7
8
9
10
11
$11,000.
12
13
14
15
16
17
18
$12,000.
19
20
21
22
23
24
25
$14,000.
26
27
28
29
30
31
  $14,000.
               
AUGUST 2026
S M T W T F S Cost
           
1
$14,000.
2
3
4
5
6
7
8
$15,000.
9
10
11
12
13
14
15
$15,000.
16
17
18
19
20
21
22
$16,500.
23
24
25
26
27
28
29
$12,500.
30
31
          $7,500.
SEPTEMBER 2026
S M T W T F S Cost
   
1
2
3
4
5
$7,500.
6
7
8
9
10
11
12
$7,500.
13
14
15
16
17
18
19
$7,000.
20
21
22
23
24
25
26
$7,000.
27
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 2026
S M T W T F S Cost
 
1
2
3
4
5
6
$4,200.
7
8
9
10
11
12
13
$4,200.
14
15
16
17
18
19
20
$4,200.
21
22
23
24
25
26
27
$5,500.
28
29
30
        $5,500.
               
JULY 2026
S M T W T F S Cost
     
1
2
3
4
$5,500.
5
6
7
8
9
10
11
$5,500.
12
13
14
15
16
17
18
$5,500.
19
20
21
22
23
24
25
$5,500.
26
27
28
29
30
31
  $6,400.
               
AUGUST 2026
S M T W T F S Cost
           
1
$6,400.
2
3
4
5
6
7
8
$6,400.
9
10
11
12
13
14
15
$6,400.
16
17
18
19
20
21
22
$6,400.
23
24
25
26
27
28
29
$6,250.
30
31
          $5,250.
SEPTEMBER 2026
S M T W T F S Cost
   
1
2
3
4
5
$5,250.
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.
               

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 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
        $22,000.
               
JULY 2026
S M T W T F S Cost
     
1
2
3
4
$22,000.
5
6
7
8
9
10
11
$22,000.
12
13
14
15
16
17
18
$22,000.
19
20
21
22
23
24
25
$22,000.
26
27
28
29
30
31
  $22,000.
               
AUGUST 2026
S M T W T F S Cost
           
1
$22,000.
2
3
4
5
6
7
8
$22,000.
9
10
11
12
13
14
15
$22,000.
16
17
18
19
20
21
22
$22,000.
23
24
25
26
27
28
29
$22,000.
30
31
          $22,000.
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
27
28
29
30
      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 2026
S M T W T F S Cost
 
1
2
3
4
5
6
$4,395.
7
8
9
10
11
12
13
$4,675..
14
15
16
17
18
19
20
$4,950.
21
22
23
24
25
26
27
$5,225.
28
29
30
        $5,995.
               
JULY 2026
S M T W T F S Cost
     
1
2
3
4
$5,995.
5
6
7
8
9
10
11
$5,495.
12
13
14
15
16
17
18
$5,745.
19
20
21
22
23
24
25
$5,745.
26
27
28
29
30
31
  $5,995.
               
AUGUST 2026
S M T W T F S Cost
           
1
$5,995.
2
3
4
5
6
7
8
$5,995.
9
10
11
12
13
14
15
$5,745.
16
17
18
19
20
21
22
$5,495.
23
24
25
26
27
28
29
$5,245.
30
31
          $5,245.
SEPTEMBER 2026
S M T W T F S Cost
   
1
2
3
4
5
$5,245.
6
7
8
9
10
11
12
$4,895.
13
14
15
16
17
18
19
$4,125.
20
21
22
23
24
25
26
$4,125.
27
28
29
30
      $3,855.