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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Boutique Sweet with Designer Interior, Large Screened Porch, AC all Bedrooms, 15 Minute Walk to Oak Bluffs Center and Inkwell Beach

All newly remodeled and furnished and tucked away on a quiet Oak Bluffs lane for the perfect reprieve after a day at the beach and shopping in town, all just a...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$10 - $8,000
June 2025
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
15
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$4,000
22
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$4,300
29
30
 $8,000
July 2025
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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31
 $8,000
August 2025
SuMoTuWeThFrSaWeek
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2
$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
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$4,000
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22
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24
25
26
27
28
29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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BEG21

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Property Details
Ideally located just 1 mile to OB Center, Many Updates, Enclosed Private Back Yard, Deck Nicely outfitted with Dining and new Living Area Grouping., Central AC

This cozy recently updated vacation home is tucked on a quiet street just on the outskirts of Oak Bluffs Center. Bike or walk to the town center, Inkwell Beach, and the picturesque Harbor...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $8,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,500
8
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14
$4,500
15
16
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21
$4,500
22
23
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28
$4,500
29
30
 $7,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
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$7,000
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$7,000
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$7,000
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$7,000
27
28
29
30
31
 $7,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,000
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$8,000
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$8,000
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$8,000
24
25
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29
30
$8,000
31
 $3,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
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$3,500
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$3,500
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$3,500
21
22
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27
$3,500
28
29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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BURBR

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Property Details
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:
$10 - $7,950
June 2025
SuMoTuWeThFrSaWeek
1
2
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5
6
7
$7,350
8
9
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12
13
14
$7,350
15
16
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21
$7,350
22
23
24
25
26
27
28
$7,350
29
30
 $7,350
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,350
6
7
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12
$7,350
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$7,350
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$7,350
27
28
29
30
31
 $7,350
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,350
3
4
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$7,350
10
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$7,350
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23
$7,950
24
25
26
27
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29
30
$7,950
31
 $7,350
September 2025
SuMoTuWeThFrSaWeek
 1
2
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$7,350
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$7,350
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$7,350
21
22
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27
$7,350
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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CASHK

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Property Details
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:
$10 - $7,800
June 2025
SuMoTuWeThFrSaWeek
1
2
3
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5
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12
13
14
15
16
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18
19
20
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25
26
27
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29
30
 $7,800
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,800
6
7
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$7,800
13
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$7,800
20
21
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$7,800
27
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30
31
 $7,800
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,800
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$7,800
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$7,800
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$7,800
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25
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$7,800
31
 
September 2025
SuMoTuWeThFrSa
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25
26
27
28
29
30
 
Clean Fee: 
$200 per week
Tax: State & Local: 
11.7
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VANAL

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Property Details
Classic Updated Gingerbread Cottage, 5 Minute Stroll Along Harbor to Beach and Town Center,

Classic Vineyard Oak Bluffs Cottage, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. The main living level features a lovely kitchen, very well stocked with...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $7,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
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5
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7
$3,000
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14
$3,000
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$3,000
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$4,000
29
30
 $5,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
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$5,000
6
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$4,500
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19
$4,500
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21
22
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26
$4,500
27
28
29
30
31
 $6,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,500
3
4
5
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$6,500
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$6,500
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18
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23
$7,500
24
25
26
27
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29
30
$4,500
31
 $4,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,500
7
8
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13
$3,000
14
15
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18
19
20
$3,000
21
22
23
24
25
26
27
$3,000
28
29
30
 $3,000
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7
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WHARG

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Property Details
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:
$10 - $7,200
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,300
8
9
10
11
12
13
14
$6,300
15
16
17
18
19
20
21
$6,300
22
23
24
25
26
27
28
$6,300
29
30
 $6,400
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,400
6
7
8
9
10
11
12
$6,400
13
14
15
16
17
18
19
$6,400
20
21
22
23
24
25
26
$6,400
27
28
29
30
31
 $7,200
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,200
3
4
5
6
7
8
9
$7,200
10
11
12
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14
15
16
$7,200
17
18
19
20
21
22
23
$7,200
24
25
26
27
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29
30
$7,200
31
 $5,700
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,700
7
8
9
10
11
12
13
14
15
16
17
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20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7

This home books Friday to Friday June-September

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BICKE

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Property Details
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:
$10 - $7,150
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,550
8
9
10
11
12
13
14
$6,000
15
16
17
18
19
20
21
$6,500
22
23
24
25
26
27
28
$6,500
29
30
 $7,150
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,150
6
7
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12
$7,150
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19
$7,150
20
21
22
23
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25
26
$7,150
27
28
29
30
31
 $7,150
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,150
3
4
5
6
7
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9
$7,150
10
11
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$7,150
17
18
19
20
21
22
23
$7,150
24
25
26
27
28
29
30
$7,150
31
 $7,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,000
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
 $6,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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HANRJ

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Property Details
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:
$10 - $7,000
June 2025
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
$4,300
22
23
24
25
26
27
28
$4,500
29
30
 $5,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
8
9
10
11
12
$5,000
13
14
15
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18
19
$6,000
20
21
22
23
24
25
26
$6,000
27
28
29
30
31
 $5,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,500
3
4
5
6
7
8
9
$7,000
10
11
12
13
14
15
16
$7,000
17
18
19
20
21
22
23
$7,000
24
25
26
27
28
29
30
$5,500
31
 $5,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,000
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
 $3,500
Clean Fee: 
$575
Tax: State & Local: 
11.7

 

 

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LIJOY

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Property Details
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:
$10 - $6,900
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,200
8
9
10
11
12
13
14
$4,600
15
16
17
18
19
20
21
$5,100
22
23
24
25
26
27
28
$5,700
29
30
 $6,200
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,200
6
7
8
9
10
11
12
$6,100
13
14
15
16
17
18
19
$6,100
20
21
22
23
24
25
26
$6,100
27
28
29
30
31
 $6,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,500
3
4
5
6
7
8
9
$6,500
10
11
12
13
14
15
16
$6,900
17
18
19
20
21
22
23
$6,500
24
25
26
27
28
29
30
$6,500
31
 $6,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,500
7
8
9
10
11
12
13
$5,500
14
15
16
17
18
19
20
$4,700
21
22
23
24
25
26
27
$4,700
28
29
30
 
Clean Fee: 
$390 per week
Tax: State & Local: 
11.7
Add Favorite
 
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GUCOB

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Property Details
Spacious Home with Heated Pool, Pool Bar with TV, Patio Surround, Deck Overlooking the Pool & Yard, Centrally Located

Spacious home with private heated pool & hot tub, tucked away in a quiet neighborhood, centrally located providing easy access to beaches and towns.  The pool, patio area, deck, & pool bar...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$10 - $6,820
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,820
8
9
10
11
12
13
14
$6,820
15
16
17
18
19
20
21
$6,820
22
23
24
25
26
27
28
$6,820
29
30
 $10,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$10,000
6
7
8
9
10
11
12
$10,000
13
14
15
16
17
18
19
$10,000
20
21
22
23
24
25
26
$10,000
27
28
29
30
31
 $10,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$10,000
3
4
5
6
7
8
9
$10,000
10
11
12
13
14
15
16
$10,000
17
18
19
20
21
22
23
$10,000
24
25
26
27
28
29
30
$10,000
31
 $6,820
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,820
7
8
9
10
11
12
13
$6,820
14
15
16
17
18
19
20
$6,820
21
22
23
24
25
26
27
$6,820
28
29
30
 $6,820
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Pool Heated to 80 degrees included in the rental rate, July & August

Pool Heated to 80 degrees, June & September, additional 350 per week surcharge

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FISHJ

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Property Details
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:
$10 - $6,800
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,000
8
9
10
11
12
13
14
$4,500
15
16
17
18
19
20
21
$4,500
22
23
24
25
26
27
28
$4,500
29
30
 $6,800
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,800
6
7
8
9
10
11
12
$6,800
13
14
15
16
17
18
19
$6,800
20
21
22
23
24
25
26
$6,800
27
28
29
30
31
 
August 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
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16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
$6,800
31
 $3,900
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,900
7
8
9
10
11
12
13
$3,900
14
15
16
17
18
19
20
$3,900
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
Add Favorite
 
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TERSM

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Property Details
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:
$10 - $6,600
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,500
8
9
10
11
12
13
14
$3,500
15
16
17
18
19
20
21
$3,900
22
23
24
25
26
27
28
$3,900
29
30
 $6,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,500
6
7
8
9
10
11
12
$6,500
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$6,500
27
28
29
30
31
 $6,400
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,400
3
4
5
6
7
8
9
$6,600
10
11
12
13
14
15
16
$6,600
17
18
19
20
21
22
23
$6,600
24
25
26
27
28
29
30
$6,600
31
 $6,600
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,600
7
8
9
10
11
12
13
$4,100
14
15
16
17
18
19
20
$4,100
21
22
23
24
25
26
27
$4,100
28
29
30
 $2,600
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

Owner books Fri to Fri July & August weeks!

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BARNJ

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Property Details
Chic, Meticulously Maintained Cape Style Home. Walk to Oak Bluffs Town Center and Beaches, Tucked on a Large Beautifully Landscaped Lot

Nestled in a beautifully landscaped lot in a serene and private neighborhood, this meticulously maintained cottage in Oak Bluffs, Martha's Vineyard, offers a perfect retreat for rental guests. With chic...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
3
Price Range:
$10 - $6,350
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,750
8
9
10
11
12
13
14
$3,750
15
16
17
18
19
20
21
$4,350
22
23
24
25
26
27
28
$4,600
29
30
 $5,750
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,750
6
7
8
9
10
11
12
$5,750
13
14
15
16
17
18
19
$6,350
20
21
22
23
24
25
26
$6,350
27
28
29
30
31
 $6,350
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,350
3
4
5
6
7
8
9
$6,350
10
11
12
13
14
15
16
$6,350
17
18
19
20
21
22
23
$6,350
24
25
26
27
28
29
30
$6,350
31
 $3,750
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,750
7
8
9
10
11
12
13
$3,750
14
15
16
17
18
19
20
$3,750
21
22
23
24
25
26
27
$3,750
28
29
30
 $3,750
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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THORB

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Property Details
Contemporary 5 Bedroom 4 Bath, Multiple Living Spaces, Walk to Oak Bluffs Center and Inkwell Beach-10 minutes

Extended families are sure to enjoy this tri-level home featuring an open floor plan on the main level, a large main living room, and three den/TV areas, one on the first level...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
5
Baths: 
4
Price Range:
$10 - $6,100
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,800
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
$5,100
29
30
 $6,100
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,100
6
7
8
9
10
11
12
$6,100
13
14
15
16
17
18
19
$6,100
20
21
22
23
24
25
26
$6,300
27
28
29
30
31
 $6,600
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,600
3
4
5
6
7
8
9
$6,600
10
11
12
13
14
15
16
$6,600
17
18
19
20
21
22
23
$6,600
24
25
26
27
28
29
30
$5,900
31
 $3,800
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,800
7
8
9
10
11
12
13
$3,800
14
15
16
17
18
19
20
$3,800
21
22
23
24
25
26
27
$3,800
28
29
30
 $2,700
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
Add Favorite
 
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NEWMJ

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Property Details

Newly update mid-century modern beach house set in the private community of homes surrounding Sengekontacket pond. The cozy summer cottage offers indoor and outdoor living at its best with a...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $6,090
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,850
8
9
10
11
12
13
14
$3,850
15
16
17
18
19
20
21
$4,960
22
23
24
25
26
27
28
$4,960
29
30
 $6,090
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,090
6
7
8
9
10
11
12
$6,090
13
14
15
16
17
18
19
$6,090
20
21
22
23
24
25
26
$6,090
27
28
29
30
31
 $6,090
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,090
3
4
5
6
7
8
9
$6,090
10
11
12
13
14
15
16
$6,090
17
18
19
20
21
22
23
$6,090
24
25
26
27
28
29
30
$6,090
31
 $6,090
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,090
7
8
9
10
11
12
13
$4,960
14
15
16
17
18
19
20
$3,850
21
22
23
24
25
26
27
$3,850
28
29
30
 $3,850
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

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