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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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:
$2,700 - $5,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,900
6
7
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11
12
$3,900
13
14
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19
$3,900
20
21
22
23
24
25
26
$4,300
27
28
29
30
 $4,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,500
4
5
6
7
8
9
10
$4,500
11
12
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$4,500
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19
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22
23
24
$4,500
25
26
27
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29
30
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$4,500
August 2027
SuMoTuWeThFrSaWeek
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2
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$5,500
8
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$5,500
15
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21
$5,500
22
23
24
25
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27
28
$5,500
29
30
31
 $5,200
September 2027
SuMoTuWeThFrSaWeek
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2
3
4
$5,200
5
6
7
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10
11
$3,700
12
13
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18
$3,200
19
20
21
22
23
24
25
$3,200
26
27
28
29
30
 $3,200
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

 

 

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COWAC

Inquire
Property Details
Lovely Cape, 7 minute walk to town and harbor area, 4 bedrooms, 3 baths, sleeps 7

Lovely 4 bedroom, 3 bath home, pristinely maintained and ideally located just on the outskirts of Oak Bluffs on a quiet street. Short walk to town center and Oak Bluffs town...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
3
Price Range:
$3,000 - $5,400
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$3,000
6
7
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12
$3,000
13
14
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$3,000
20
21
22
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25
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$3,800
27
28
29
30
 $4,700
July 2027
SuMoTuWeThFrSaWeek
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2
3
$4,700
4
5
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10
$4,700
11
12
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$4,700
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19
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$4,700
25
26
27
28
29
30
31
$5,350
August 2027
SuMoTuWeThFrSaWeek
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2
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$5,400
8
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$5,600
15
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21
$5,400
22
23
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25
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28
$4,400
29
30
31
 $3,200
September 2027
SuMoTuWeThFrSaWeek
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2
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$3,200
5
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$3,200
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$3,000
19
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25
$3,000
26
27
28
29
30
 $3,000
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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PEOTA

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Property Details
Pristine Water view Home, Located in the Community of Homes known as Water View Farms, Walk to Private Association Waterfront, Great Play Beach, Launch Kayaks

This charming updated home is set in idyllic Water View Farms overlooking Sengekontacket pond.  This well-thought-out home offers a beautifully landscaped yard and cottage-style living with indoor spaces that transition...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,000 - $5,350
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,550
6
7
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10
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12
$3,550
13
14
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$4,050
20
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25
26
$4,770
27
28
29
30
 $5,350
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,350
4
5
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10
$5,350
11
12
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$5,350
18
19
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$5,350
25
26
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30
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$5,820
August 2027
SuMoTuWeThFrSaWeek
1
2
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$5,820
8
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$5,820
15
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$5,820
22
23
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27
28
$4,770
29
30
31
 $3,550
September 2027
SuMoTuWeThFrSaWeek
 1
2
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$3,550
5
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$3,050
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$3,050
19
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21
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25
$2,550
26
27
28
29
30
 $2,050
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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VANAL

Inquire
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:
$3,500 - $5,000
June 2027
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
 $4,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,000
4
5
6
7
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9
10
$5,000
11
12
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$4,500
18
19
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22
23
24
$4,500
25
26
27
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29
30
31
$4,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$7,500
8
9
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11
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13
14
$7,500
15
16
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18
19
20
21
$7,500
22
23
24
25
26
27
28
29
30
31
 $4,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,500
5
6
7
8
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10
11
$4,500
12
13
14
15
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18
$3,500
19
20
21
22
23
24
25
$3,500
26
27
28
29
30
 $3,500
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

Rates reduced for available weeks June - July - see calendar for adjusted rates

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CENCR

Inquire
Property Details
Oak Bluffs Summer Retreat, Large Private Deck, Lagoon Beach Rights -Great Area for Kayaking.

Spacious sun-filled home features open living spaces, hardwood floors throughout, 4 bedrooms and sleeps 8.

Exterior features include two decks, one sunny deck at the front of the house, and a large private...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,000 - $5,000
June 2027
SuMoTuWeThFrSa
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July 2027
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August 2027
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September 2027
SuMoTuWeThFrSa
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Clean Fee: 
$480 per week
Tax: State & Local: 
11.7
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WILCM

Inquire
Property Details
Hidden Cove Retreat, Walk to Association Tennis/Pickleball Courts, 3 Bedrooms, 2.5 Baths, Screened Porch and Deck

Nestled in the charming Hidden Cove community, this adorable contemporary home resides on a tranquil street within walking distance of the association's tennis/pickleball courts. Its central location places it just a...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$4,000 - $5,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
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5
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19
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21
22
23
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25
26
27
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29
30
 $4,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,500
4
5
6
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8
9
10
$4,500
11
12
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15
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17
$4,500
18
19
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21
22
23
24
$4,500
25
26
27
28
29
30
31
$4,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,500
8
9
10
11
12
13
14
$6,500
15
16
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18
19
20
21
$5,000
22
23
24
25
26
27
28
$5,000
29
30
31
 $4,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
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$4,000
5
6
7
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12
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16
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20
21
22
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24
25
26
27
28
29
30
 
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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BRANF

Inquire
Property Details
Spacious Colonial with Contemporary Detailing in Fresh Pond Estates, Multiple Living Spaces, Screened Porch, Spacious Deck, AC, Wifi, Beautifully Furnished, Bike Paths at the head of the Road

Spacious, 4 bedroom 3.5 bath contemporary home set in a quiet lovely community on the outskirts of Oak Bluffs. . The main living level features an open concept and hosts a family...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,700 - $5,000
June 2027
SuMoTuWeThFrSa
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July 2027
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August 2027
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September 2027
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29
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Clean Fee: 
$500 per week ($375 for interim cleaning on multiple week rentals)
Tax: State & Local: 
11.7
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KEANM

Inquire
Property Details
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:
$2,000 - $5,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,500
6
7
8
9
10
11
12
$2,500
13
14
15
16
17
18
19
$3,000
20
21
22
23
24
25
26
$3,000
27
28
29
30
 $4,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,800
4
5
6
7
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9
10
$4,800
11
12
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$4,800
18
19
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23
24
$4,800
25
26
27
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29
30
31
$4,800
August 2027
SuMoTuWeThFrSaWeek
1
2
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$5,000
8
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$5,000
15
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$5,000
22
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27
28
$5,000
29
30
31
 $4,500
September 2027
SuMoTuWeThFrSaWeek
 1
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$4,500
5
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29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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DENAL

Inquire
Property Details

Charming, 4-bedroom Oak Bluffs Home, pristinely maintained!  The large wraparound porch and backyard patio areas provide the perfect venue for relaxing when not at the beach or out and about...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,000 - $5,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,000
6
7
8
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10
11
12
$3,000
13
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$3,000
20
21
22
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25
26
$3,000
27
28
29
30
 $5,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,000
4
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$5,000
11
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$5,000
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$5,000
25
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$5,000
August 2027
SuMoTuWeThFrSaWeek
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$5,000
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$5,000
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$5,000
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$5,000
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 $4,000
September 2027
SuMoTuWeThFrSaWeek
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$4,000
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$2,000
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$2,000
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$2,000
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30
 $2,000
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Parking for two cars only, no on-street parking!

 

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DUREJ

Inquire
Property Details

This luxuriously updated tri-level condo retreat at Quail Run in the community of homes known as Sengekontacket, has been transformed, bringing a fresh, coastal feel to every corner. The end...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
1
Price Range:
$3,500 - $5,000
June 2027
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September 2027
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
Add Favorite
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TOTHG

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Property Details

Note: Older style TVs seen in photos have been replaced. 

This bright and classic summer cottage is ideally located just one mile from Oak Bluffs town center and all the...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$4,000 - $4,950
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSaWeek
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$4,950
August 2027
SuMoTuWeThFrSaWeek
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$4,950
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$4,950
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$4,950
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$4,950
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 $4,000
September 2027
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$4,000
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$4,000
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29
30
 $4,000
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
Add Favorite
 
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GLOVL

Inquire
Property Details
Lovely Contemporary Home, Quiet Location in Pond View, Private Back Yard, Porch & Deck

Beautifully maintained, family-friendly home.

Lovely 3 Bedroom, 2.5 bath home situated in a quiet enclave of homes known as Pond View and just 2.5 miles to the center of Oak Bluffs....Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$4,700 - $4,900
June 2027
SuMoTuWeThFrSaWeek
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30
 $4,700
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,700
4
5
6
7
8
9
10
$4,700
11
12
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$4,700
18
19
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$4,700
25
26
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30
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$4,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
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$4,900
8
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$4,900
15
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$4,900
22
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$4,900
29
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31
 
September 2027
SuMoTuWeThFrSa
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Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
Add Favorite
 
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DONOP

Inquire
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:
$2,400 - $4,720
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,400
6
7
8
9
10
11
12
$3,050
13
14
15
16
17
18
19
$3,050
20
21
22
23
24
25
26
$3,200
27
28
29
30
 $4,100
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,100
4
5
6
7
8
9
10
$4,100
11
12
13
14
15
16
17
$4,300
18
19
20
21
22
23
24
$4,300
25
26
27
28
29
30
31
$4,600
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,720
8
9
10
11
12
13
14
$4,720
15
16
17
18
19
20
21
$4,720
22
23
24
25
26
27
28
$3,570
29
30
31
 $4,100
September 2027
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
 $4,100
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
Add Favorite
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GRATD

Inquire
Property Details
Located in the Heart of Oak Bluffs, 5 Minute Walk to OB Center and 2 Blocks to the Beach
Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
2
Price Range:
$2,000 - $4,700
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSa
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August 2027
SuMoTuWeThFrSa
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September 2027
SuMoTuWeThFrSa
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Clean Fee: 
$260 per week
Tax: State & Local: 
11.7
Add Favorite
 
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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 - $4,600
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,600
6
7
8
9
10
11
12
$2,600
13
14
15
16
17
18
19
$2,800
20
21
22
23
24
25
26
$2,800
27
28
29
30
 $3,900
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,900
4
5
6
7
8
9
10
$3,900
11
12
13
14
15
16
17
$3,900
18
19
20
21
22
23
24
$3,900
25
26
27
28
29
30
31
$3,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,600
8
9
10
11
12
13
14
$4,600
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 $3,100
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,100
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 $2,600
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7

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