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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The Boathouse, East Chop Location, Gorgeous Water and Sunset Views, Architect Designed Gem

Designed by a renowned island architect and custom-crafted,  The Boathouse underwent construction and total renovation in 2016 and is now a terrific year-round home.  The exterior of the house maintains...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
3
Baths: 
2
Price Range:
$4,500 - $8,000
June 2024
SuMoTuWeThFrSaWeek
 1
$6,000
2
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$6,500
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$6,500
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$6,500
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$6,500
30
 $8,000
July 2024
SuMoTuWeThFrSaWeek
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$8,000
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$8,000
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$8,000
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$8,000
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 $8,000
August 2024
SuMoTuWeThFrSaWeek
 1
2
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$8,000
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$8,000
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$8,000
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$8,000
25
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$8,000
September 2024
SuMoTuWeThFrSaWeek
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$8,000
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$6,500
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$6,500
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$6,500
29
30
 $4,500
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Two-week minimum stay per owner! 

 

 

 
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DAVI5

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Lovely Oak Bluffs Cape, Centrally Located, Newly Updated, 4 Bedrooms, Sleeps 8-9, Large Landscaped Yard
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$3,000 - $7,900
June 2024
SuMoTuWeThFrSaWeek
 1
$3,500
2
3
4
5
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14
15
$3,500
16
17
18
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21
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$3,500
23
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25
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28
29
$4,500
30
 $5,800
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,800
7
8
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$5,800
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$5,800
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22
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25
26
27
$7,000
28
29
30
31
 $7,800
August 2024
SuMoTuWeThFrSaWeek
 1
2
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$7,800
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5
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$7,900
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$4,900
September 2024
SuMoTuWeThFrSaWeek
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$4,500
8
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$4,000
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$4,000
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$4,000
29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
 
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CASHK

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Lovely Home, Centrally Located, Bike Paths, AC all Rooms

This lovely 3 bedroom home features an open floor plan on the living level, colorful decor, window AC in all rooms, and a well-equipped modern kitchen. The home is nicely situated...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
2
Price Range:
$7,800 - $7,800
June 2024
SuMoTuWeThFrSaWeek
 1
$6,500
2
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$4,500
9
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$6,500
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$6,500
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27
28
29
$6,500
30
 $7,800
July 2024
SuMoTuWeThFrSaWeek
 1
2
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5
6
$7,800
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$7,800
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$7,800
21
22
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$7,800
28
29
30
31
 $7,800
August 2024
SuMoTuWeThFrSaWeek
 1
2
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$7,800
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$7,800
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$7,800
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$7,800
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$7,800
September 2024
SuMoTuWeThFrSa
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26
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29
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Clean Fee: 
$200 per week
Tax: State & Local: 
11.7
 
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PRIAN

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Beautiful Contemporary Home, Designer Details Throughout.

Gorgeous light-filled vacation home tucked away in a private community centrally located just minutes from Oak Bluffs, Edgartown, and several beautiful beaches. Privately situated, this home features multiple living areas,...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$6,700 - $7,300
June 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
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15
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$6,300
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$6,700
30
 $7,300
July 2024
SuMoTuWeThFrSaWeek
 1
2
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$7,300
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$7,000
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$7,000
21
22
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25
26
27
$7,300
28
29
30
31
 $7,300
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$7,300
4
5
6
7
8
9
10
$7,800
11
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$7,800
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19
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$7,800
25
26
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30
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$7,300
September 2024
SuMoTuWeThFrSa
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29
30
 
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
 
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BICKE

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East Chop Area, Tri-Level Home with Distant Water views, Located just 1.5 Mi to Oak Bluffs Center

Beautiful summer home with distant water views, located in the desirable East Chop neighborhood.  This 4 bedroom, 3 bath home is located just 1.5 miles from Oak Bluffs Center & Beach. 

The...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$5,550 - $7,150
June 2024
SuMoTuWeThFrSaWeek
 1
$6,000
2
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$5,550
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$6,000
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$6,500
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$6,500
30
 $7,150
July 2024
SuMoTuWeThFrSaWeek
 1
2
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$7,150
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$7,150
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$7,150
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$7,000
28
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30
31
 $7,000
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$7,000
4
5
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$7,150
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$7,150
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$7,150
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30
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$7,150
September 2024
SuMoTuWeThFrSaWeek
1
2
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$7,000
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$6,500
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$6,500
22
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25
26
27
28
$6,500
29
30
 $6,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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BURBR

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Perfect Retreat for Large Families, 1.5 miles to Oak Bluffs Town Center & Beach, Bike Path at end of Street

Spacious and perfect for extended families, featuring multiple attractively furnished living areas, and sleeps 13 comfortably. The lower level of the house features a queen bed, kitchenette, den area with...Read more

Location: 
Oak Bluffs
Sleeps: 
11
Bedrooms: 
5
Baths: 
3
Price Range:
$7,000 - $7,000
June 2024
SuMoTuWeThFrSaWeek
 1
$6,500
2
3
4
5
6
7
8
$7,000
9
10
11
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13
14
15
$7,000
16
17
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21
22
$7,000
23
24
25
26
27
28
29
$7,000
30
 $7,000
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,000
7
8
9
10
11
12
13
$7,000
14
15
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$7,000
21
22
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25
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27
$7,000
28
29
30
31
 $7,000
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$7,000
4
5
6
7
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9
10
$7,000
11
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$7,000
18
19
20
21
22
23
24
$7,000
25
26
27
28
29
30
31
$7,000
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$7,000
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: 
$450 per week
Tax: State & Local: 
11.7
 
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TRAVM

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Updated East Chop Area Summer Retreat, Great Proximity to Town Center and Beaches, Cottage Styling with All the Modern Amenities, Central A/C. Covered Porch and Open Patio Areas.

Visitors will enjoy this delightful &  comfortable 4 bedroom, 3 bath home in the desirable East Chop area of Oak Bluffs. 

Relax in the breeze with your morning coffee on the front...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$5,200 - $7,000
June 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
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7
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10
11
12
13
14
15
16
17
18
19
20
21
22
23
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25
26
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28
29
30
 $5,200
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,200
7
8
9
10
11
12
13
$5,200
14
15
16
17
18
19
20
$5,200
21
22
23
24
25
26
27
28
29
30
31
 $6,800
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$6,800
4
5
6
7
8
9
10
$7,000
11
12
13
14
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17
$7,000
18
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28
29
30
31
September 2024
SuMoTuWeThFrSa
1
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25
26
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29
30
 
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
 
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HANRJ

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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 2024
SuMoTuWeThFrSaWeek
 1
$4,300
2
3
4
5
6
7
8
$4,300
9
10
11
12
13
14
15
$4,300
16
17
18
19
20
21
22
$4,300
23
24
25
26
27
28
29
$5,200
30
 $6,000
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,000
7
8
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13
$6,000
14
15
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$6,000
21
22
23
24
25
26
27
$6,000
28
29
30
31
 $7,000
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$7,000
4
5
6
7
8
9
10
$7,000
11
12
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15
16
17
$7,000
18
19
20
21
22
23
24
$7,000
25
26
27
28
29
30
31
$5,900
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,000
8
9
10
11
12
13
14
$4,000
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,000
29
30
 $3,500
Clean Fee: 
$575
Tax: State & Local: 
11.7

 

 

 
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THOMS

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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:
$2,500 - $6,800
June 2024
SuMoTuWeThFrSaWeek
 1
$3,100
2
3
4
5
6
7
8
$3,800
9
10
11
12
13
14
15
$3,800
16
17
18
19
20
21
22
$3,800
23
24
25
26
27
28
29
$5,500
30
 $6,300
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,300
7
8
9
10
11
12
13
$6,300
14
15
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17
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19
20
$6,300
21
22
23
24
25
26
27
$6,300
28
29
30
31
 $6,800
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$6,800
4
5
6
7
8
9
10
$6,800
11
12
13
14
15
16
17
$6,800
18
19
20
21
22
23
24
$6,800
25
26
27
28
29
30
31
$6,800
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,500
8
9
10
11
12
13
14
$3,800
15
16
17
18
19
20
21
$3,800
22
23
24
25
26
27
28
$3,800
29
30
 $3,800
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
 
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FISHJ

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Stylish Contemporary Vacation Home situated in Meadow View Farms, Open Light Filled Design, Expansive Private Deck

Come and enjoy this light-filled, beautifully maintained, three-level contemporary home complete with gardens, landscaped yard, and a children’s backyard playground.  

The main level features an open kitchen, dining, and TV/living...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$3,500 - $6,800
June 2024
SuMoTuWeThFrSaWeek
 1
$4,500
2
3
4
5
6
7
8
$4,000
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
 $6,800
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,800
7
8
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10
11
12
13
$6,800
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$6,800
21
22
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25
26
27
$6,800
28
29
30
31
 $6,800
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$6,800
4
5
6
7
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9
10
$6,800
11
12
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$6,800
18
19
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21
22
23
24
$6,800
25
26
27
28
29
30
31
$6,800
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,900
8
9
10
11
12
13
14
$3,900
15
16
17
18
19
20
21
$3,900
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
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WHARG

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Lovely Home in a quiet Neighborhood. Walk to Town Center and Inkwell Beach, Large Private Deck, Room AC

Spacious sun-filled contemporary home located on a quiet private street, a 10-minute walk to town center, Inkwell Beach, and the harborfront.

The first level features a spacious kitchen with stainless steel...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$5,700 - $6,600
June 2024
SuMoTuWeThFrSaWeek
 1
$5,200
2
3
4
5
6
7
8
$5,700
9
10
11
12
13
14
15
$5,700
16
17
18
19
20
21
22
$5,700
23
24
25
26
27
28
29
$5,700
30
 $6,100
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,100
7
8
9
10
11
12
13
$6,100
14
15
16
17
18
19
20
$6,100
21
22
23
24
25
26
27
$6,100
28
29
30
31
 $6,600
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$6,600
4
5
6
7
8
9
10
$6,600
11
12
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17
$6,600
18
19
20
21
22
23
24
$6,600
25
26
27
28
29
30
31
$6,600
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,700
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9
10
11
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29
30
 $6,000
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

This home books Friday to Friday June-September

 
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WESTW

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Tri Level Oak Bluffs Home, Central A/C, Set in Private Community of Sengekontacket, Multiple Living Spaces, Large Deck, Patio Area, Association Tennis

Privately situated on a hilltop in Sengekontacket, -spacious tri-level, 4000 sq ft contemporary home. Set in a wonderful, family friendly community, offering association tennis courts, and an association dock on Sengekontacket Pond...Read more

Location: 
Oak Bluffs
Sleeps: 
14
Bedrooms: 
5
Baths: 
2
Price Range:
$5,000 - $6,500
June 2024
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
$6,300
23
24
25
26
27
28
29
$6,300
30
 $8,500
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$8,500
7
8
9
10
11
12
13
$9,000
14
15
16
17
18
19
20
$9,000
21
22
23
24
25
26
27
$10,000
28
29
30
31
 $10,000
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$10,000
4
5
6
7
8
9
10
$12,000
11
12
13
14
15
16
17
$12,000
18
19
20
21
22
23
24
$8,500
25
26
27
28
29
30
31
$7,500
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,500
8
9
10
11
12
13
14
$5,500
15
16
17
18
19
20
21
$5,500
22
23
24
25
26
27
28
$5,000
29
30
 $5,000
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Owner has 5 night Min required in October & Shoulder months, $600 per night plus fees. Please Inquire.

 
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LIJOY

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Hidden Cove Summer Retreat, Newly Updated, Association Tennis Courts, Bike Paths at Entrance to Neighborhood, Multiple Beaches Near By

Summer Dream offers the opportunity for a relaxing vacation in a beautiful environment. This 4 bedroom, 2 ½ bath home has a beautiful new kitchen and new living room furnishings...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,200 - $6,500
June 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
$4,200
9
10
11
12
13
14
15
$4,600
16
17
18
19
20
21
22
$5,100
23
24
25
26
27
28
29
$5,700
30
 $6,200
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,200
7
8
9
10
11
12
13
$6,100
14
15
16
17
18
19
20
$6,100
21
22
23
24
25
26
27
$6,100
28
29
30
31
 $6,500
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$6,500
4
5
6
7
8
9
10
$6,500
11
12
13
14
15
16
17
$6,900
18
19
20
21
22
23
24
$6,500
25
26
27
28
29
30
31
$6,500
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,500
8
9
10
11
12
13
14
$5,500
15
16
17
18
19
20
21
$4,700
22
23
24
25
26
27
28
$4,700
29
30
 
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
 
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TERSM

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Modern, Newly Renovated, Architecturally Significant Beach Cottage Design. Close to Town and Beaches, Tucked in the Lovely Community of Summer Homes, Waterview Farms!

Gorgeous all newly renovated and newly furnished mid-century beach cottage, now a modern vacation oasis designed by the prominent interior design firm, - Tersigni Palachek. This eloquent, yet beachy home offers...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,600 - $6,500
June 2024
SuMoTuWeThFrSaWeek
 1
$2,700
2
3
4
5
6
7
8
$3,850
9
10
11
12
13
14
15
$4,060
16
17
18
19
20
21
22
$4,100
23
24
25
26
27
28
29
$4,100
30
 $6,500
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,500
7
8
9
10
11
12
13
$6,500
14
15
16
17
18
19
20
$6,500
21
22
23
24
25
26
27
$6,500
28
29
30
31
 $6,500
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$6,500
4
5
6
7
8
9
10
$6,500
11
12
13
14
15
16
17
$6,500
18
19
20
21
22
23
24
$6,500
25
26
27
28
29
30
31
$4,300
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,300
8
9
10
11
12
13
14
$4,300
15
16
17
18
19
20
21
$4,100
22
23
24
25
26
27
28
$4,100
29
30
 $4,100
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

Owner books Fri to Fri July & August weeks!

 
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SUTTJ

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Newly Renovated, Modern Cottage Luxury, Professionally Decorated, 1 mile from Oak Bluffs Center & Beach

Stunning new stylish renovation, professionally decorated, a step above your average rental, and just 1 mile to the Harbor and the center of Oak Bluffs!

The main living level features an...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,700 - $6,500
June 2024
SuMoTuWeThFrSaWeek
 1
$3,000
2
3
4
5
6
7
8
$3,000
9
10
11
12
13
14
15
$3,500
16
17
18
19
20
21
22
$3,800
23
24
25
26
27
28
29
$4,950
30
 $5,800
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,800
7
8
9
10
11
12
13
$5,800
14
15
16
17
18
19
20
$5,800
21
22
23
24
25
26
27
$6,000
28
29
30
31
 $6,000
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$6,000
4
5
6
7
8
9
10
$6,000
11
12
13
14
15
16
17
$6,500
18
19
20
21
22
23
24
$6,500
25
26
27
28
29
30
31
$6,000
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,600
8
9
10
11
12
13
14
$3,500
15
16
17
18
19
20
21
$3,500
22
23
24
25
26
27
28
$3,500
29
30
 $2,900
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

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