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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Lovely Oak Bluffs Home, 3 Bedrooms, 2.5 Baths, Sleeps 7. Set just on the Outskirts of Oak Bluffs Center

Lovely 3 bedroom, 2.5 bath home that sleeps 7. This sweet home is bordered by a large yard and is located just on the outskirts of Oak Bluffs. The patio...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$2,950 - $4,600
June 2026
SuMoTuWeThFrSaWeek
 1
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$3,000
28
29
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 $4,600
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$4,600
5
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$4,600
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$4,600
19
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25
$4,600
26
27
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29
30
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 $4,600
August 2026
SuMoTuWeThFrSaWeek
 1
$4,600
2
3
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8
$4,700
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$4,700
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$4,700
23
24
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27
28
29
$4,700
30
31
 $4,700
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,700
6
7
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$3,000
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$3,000
20
21
22
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25
26
27
28
29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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DONOP

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Property Details
Hidden Cove, Centrally Located to Beaches and Towns, Association Tennis Courts, A/C, WiFi

Centrally located in the Hidden Cove community of homes on the outskirts of Oak Bluffs. Lovely area to bike, walk, or play tennis at the association courts. 

The main level features an...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,600 - $4,200
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,400
7
8
9
10
11
12
13
$3,050
14
15
16
17
18
19
20
$3,050
21
22
23
24
25
26
27
$3,200
28
29
30
 $4,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,000
5
6
7
8
9
10
11
$4,000
12
13
14
15
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18
$4,200
19
20
21
22
23
24
25
$4,200
26
27
28
29
30
31
 $4,500
August 2026
SuMoTuWeThFrSaWeek
 1
$4,500
2
3
4
5
6
7
8
$4,500
9
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15
$4,500
16
17
18
19
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21
22
$4,500
23
24
25
26
27
28
29
$3,400
30
31
 $2,600
September 2026
SuMoTuWeThFrSaWeek
 1
2
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5
$2,600
6
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$2,600
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$2,600
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25
26
$2,600
27
28
29
30
 $2,600
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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DHANM

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Property Details
Adorable Oak Bluffs Cottage Just Over a Mile to the Village Center and Town Beaches, Porch, Deck, 4 Bedrooms, 2 Baths

Nestled on a quiet street, this recently updated residence boasts delightful indoor and outdoor living areas. The entrance porch offers cozy seating with wicker chairs and a small dining table that...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$2,300 - $4,200
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,000
7
8
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12
13
$3,000
14
15
16
17
18
19
20
$3,600
21
22
23
24
25
26
27
$4,200
28
29
30
 $4,200
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,200
5
6
7
8
9
10
11
$4,200
12
13
14
15
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18
$4,200
19
20
21
22
23
24
25
$4,200
26
27
28
29
30
31
 $4,200
August 2026
SuMoTuWeThFrSaWeek
 1
$4,200
2
3
4
5
6
7
8
$5,000
9
10
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14
15
$5,500
16
17
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19
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21
22
$5,700
23
24
25
26
27
28
29
$4,000
30
31
 $4,200
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$4,200
6
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$3,000
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$3,000
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21
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25
26
$3,000
27
28
29
30
 $2,300
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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SACHE

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Property Details
Waterview Farms, Water view

Lovely contemporary home in one of the island's premier community settings, Waterview Farms. Close to Farm Neck Golf Course and tennis and a short distance to town and beaches....Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$3,000 - $4,160
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,460
7
8
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10
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13
$3,460
14
15
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20
$3,460
21
22
23
24
25
26
27
$3,460
28
29
30
 $4,160
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,160
5
6
7
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9
10
11
$4,160
12
13
14
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18
$4,160
19
20
21
22
23
24
25
$4,160
26
27
28
29
30
31
 $4,160
August 2026
SuMoTuWeThFrSaWeek
 1
$4,160
2
3
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$4,160
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$4,160
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$4,160
23
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25
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27
28
29
$4,160
30
31
 $4,160
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,160
6
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12
$4,160
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$4,160
20
21
22
23
24
25
26
$4,160
27
28
29
30
 $4,160
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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PETEV

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Property Details
Lovely Waterfront Home, Oak Bluffs, Gorgeous Water Views, Association Tennis Courts, AC, Wi-fi, Bike Paths Nearby

Note: Pricing for this waterfront home takes into account that this is an older-style home. Please note that baths and kitchen have not been updated

MVVR Exclusive! Spacious, traditional waterfront Cape Cod style home...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
4
Baths: 
2
Price Range:
$2,460 - $4,100
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,600
7
8
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10
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$3,600
14
15
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$3,600
21
22
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29
30
 $4,100
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,100
5
6
7
8
9
10
11
$4,100
12
13
14
15
16
17
18
$4,100
19
20
21
22
23
24
25
$4,100
26
27
28
29
30
31
 $4,100
August 2026
SuMoTuWeThFrSaWeek
 1
$4,100
2
3
4
5
6
7
8
$4,100
9
10
11
12
13
14
15
$4,100
16
17
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20
21
22
$4,100
23
24
25
26
27
28
29
$3,910
30
31
 $3,660
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,660
6
7
8
9
10
11
12
$3,660
13
14
15
16
17
18
19
20
21
22
23
24
25
26
$2,460
27
28
29
30
 $2,460
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
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TAYLJ

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Property Details
SPACIOUS LIGHTFILLED 3 BEDROOM, 3 BATH HOME, PRIVATE DECK WITH PATIO DINING, 7 MINUTE DRIVE TO THE CENTER OF OAK BLUFFS AND INKWELL BEACH

Experience the best of Island living—peaceful residential surroundings, the vibrant shops and attractions of the three Down Island towns (Oak Bluffs, Edgartown, and Vineyard Haven), and quick access to public...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$3,500 - $4,100
June 2026
SuMoTuWeThFrSaWeek
 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
 $4,100
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,100
5
6
7
8
9
10
11
$4,100
12
13
14
15
16
17
18
$4,100
19
20
21
22
23
24
25
$4,100
26
27
28
29
30
31
 $4,100
August 2026
SuMoTuWeThFrSaWeek
 1
$4,100
2
3
4
5
6
7
8
$5,200
9
10
11
12
13
14
15
$5,200
16
17
18
19
20
21
22
$5,200
23
24
25
26
27
28
29
$5,200
30
31
 $3,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
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
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

 

 

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KOEOB

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Property Details
Adorable Updated 2 Bedroom 1.5 Bath Cottage, Walk to Town, Harbor and Beach

If you are looking for an adorable cottage-style home in the center of Oak Bluffs this newly updated, tastefully decorated 2 bedroom, with one full bath and a half bath, is sure to...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
1
Price Range:
$2,500 - $3,800
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,500
7
8
9
10
11
12
13
$2,500
14
15
16
17
18
19
20
$2,700
21
22
23
24
25
26
27
$2,700
28
29
30
 $3,800
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,800
5
6
7
8
9
10
11
$3,800
12
13
14
15
16
17
18
$3,800
19
20
21
22
23
24
25
$3,800
26
27
28
29
30
31
 $3,800
August 2026
SuMoTuWeThFrSaWeek
 1
$3,800
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
$3,500
30
31
 $3,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,000
6
7
8
9
10
11
12
$2,500
13
14
15
16
17
18
19
$2,500
20
21
22
23
24
25
26
$2,500
27
28
29
30
 $2,500
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
Add Favorite
 
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KLEIB

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Property Details
Lagoon Waterfront & Beachfront, Spectacular Water views, Room A/C, WIFI

Adorable waterfront & beachfront cottage.   Immaculately maintained, lots of summer charm, fantastic views of the Vineyard Sound and Lagoon from the large patio area. Stairs lead directly to a...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$2,250 - $3,640
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,960
7
8
9
10
11
12
13
$3,260
14
15
16
17
18
19
20
$3,270
21
22
23
24
25
26
27
$3,640
28
29
30
 $3,980
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,980
5
6
7
8
9
10
11
$4,070
12
13
14
15
16
17
18
$4,090
19
20
21
22
23
24
25
$4,200
26
27
28
29
30
31
 $4,300
August 2026
SuMoTuWeThFrSaWeek
 1
$4,300
2
3
4
5
6
7
8
$4,390
9
10
11
12
13
14
15
$4,390
16
17
18
19
20
21
22
$4,200
23
24
25
26
27
28
29
$3,850
30
31
 $3,300
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,300
6
7
8
9
10
11
12
$2,820
13
14
15
16
17
18
19
$2,560
20
21
22
23
24
25
26
$2,460
27
28
29
30
 $2,350
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
Add Favorite
 
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FRANL

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Property Details
Modern, Light filled Home, Located at end of Quiet Street, 1.5 Miles to Oak Bluffs center, Harbor Area and one of many Public Beaches

Perfect Oak Bluffs vacation home.  Located just 1.5 miles to the village center, town beach, and centrally located to the towns of Vineyard Haven, Edgartown, and multiple public beaches.  This...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$2,300 - $3,600
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
$3,600
28
29
30
 $3,600
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,600
5
6
7
8
9
10
11
$3,600
12
13
14
15
16
17
18
$3,600
19
20
21
22
23
24
25
$3,600
26
27
28
29
30
31
 $3,600
August 2026
SuMoTuWeThFrSaWeek
 1
$3,600
2
3
4
5
6
7
8
$3,600
9
10
11
12
13
14
15
$3,600
16
17
18
19
20
21
22
$3,600
23
24
25
26
27
28
29
$3,300
30
31
 $2,800
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,800
6
7
8
9
10
11
12
$2,800
13
14
15
16
17
18
19
$2,800
20
21
22
23
24
25
26
$2,800
27
28
29
30
 $2,300
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
Add Favorite
 
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MAHAB

(0)Inquire/Share
Property Details
Sweet Updated 3 Bedroom Home, Nicely Tucked in Lightly Wooded Area, Central Location, Beaches and Towns just a short Drive!

Lovely reverse contemporary home with a large deck, outdoor dining, and grill area. The upper level of this home features an open kitchen, living, and dining area stylishly furnished.  Nicely equipped kitchen...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
1
Price Range:
$3,500 - $3,500
June 2026
SuMoTuWeThFrSaWeek
 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
$4,000
28
29
30
 $4,000
July 2026
SuMoTuWeThFrSaWeek
 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
 $4,000
August 2026
SuMoTuWeThFrSaWeek
 1
$4,000
2
3
4
5
6
7
8
$4,000
9
10
11
12
13
14
15
$4,000
16
17
18
19
20
21
22
$4,000
23
24
25
26
27
28
29
$4,000
30
31
 $4,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
6
7
8
9
10
11
12
$4,000
13
14
15
16
17
18
19
$3,500
20
21
22
23
24
25
26
$3,500
27
28
29
30
 $3,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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LODGJ

(0)Inquire/Share
Property Details
Meadow View Farms, Out of Town, Association Tennis, Hi Speed Internet
Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,900 - $2,900
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
$2,900
21
22
23
24
25
26
27
$2,900
28
29
30
 $3,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,000
5
6
7
8
9
10
11
$3,000
12
13
14
15
16
17
18
$3,000
19
20
21
22
23
24
25
$3,000
26
27
28
29
30
31
 $3,000
August 2026
SuMoTuWeThFrSaWeek
 1
$3,000
2
3
4
5
6
7
8
$3,000
9
10
11
12
13
14
15
$3,000
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$3,000
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$3,000
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 $2,900
September 2026
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$2,900
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$2,900
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$2,900
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Clean Fee: 
$360 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: 
4
Baths: 
4
Price Range:
$2,700 - $2,700
June 2026
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July 2026
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August 2026
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September 2026
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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GOLLB

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Property Details
Waterfront, Private Beach, Gorgeous Water Views, Room AC, Wifi

MVVR EXCLUSIVE:  Classic, beach cottage with spectacular views across the sound, calm water swimming, and a great area for kayaking. The open kitchen, dining, and living areas are enhanced by the wall of windows...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
3
Baths: 
1
Price Range:
$1,900 - $2,700
June 2026
SuMoTuWeThFrSaWeek
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2
3
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$2,250
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$2,300
14
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$2,700
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$2,900
28
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 $3,200
July 2026
SuMoTuWeThFrSaWeek
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2
3
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$3,200
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$3,200
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$3,200
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$3,200
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31
 $3,300
August 2026
SuMoTuWeThFrSaWeek
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$3,300
2
3
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$3,300
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$3,300
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$3,300
23
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$2,900
30
31
 $2,000
September 2026
SuMoTuWeThFrSaWeek
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2
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$2,000
6
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$2,000
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$2,000
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$2,000
27
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30
 $1,900
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7

Cottage books Tuesday to Tuesday July & August weeks

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BROWL

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Property Details
Stunning Tri-Level Home, Heated Pool, Screened Porch, Beautifully Landscaped, Walk to Association Tennis Courts

Featured MVVR Listing:

Beautiful Coastal Inspired Retreat features multiple living spaces, a pool, a bluestone patio area, and a deck with an outdoor dining and grill area.  This beautiful home is...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$70 - $70
June 2026
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July 2026
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August 2026
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September 2026
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Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

Pool Heated to 80 degrees included in rental rate last Saturday in June to the first Saturday in September. 

 

Pool Heated to 80 degrees, June & September weeks additional $300 propane surcharge per week. 

   

 

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ALVEN

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Property Details
Spacious Oak Bluffs Home, Heated Pool 16 x 32, 4 bedrooms & 3.5 baths sleeps 8

This charming and spacious 4-bedroom, 3.5-bath home offers multiple living areas, including a main living room with TV, a cozy sitting room, and a lower-level family room featuring a TV,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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 $14,000
August 2026
SuMoTuWeThFrSaWeek
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$14,000
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$14,000
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$14,000
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$14,000
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September 2026
SuMoTuWeThFrSa
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Clean Fee: 
$550
Tax: State & Local: 
11.7

Two week minimum stay required, house can be rented Sat 8/8 to 8/22 or 8/9 to 8/23

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