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

MVVR Exclusive! Spacious, traditional waterfront Cape Cod style home tucked away on the shores of Sengekontacket Lagoon in a community of homes - featuring gorgeous views, mini-split AC units in main living areas,...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
4
Baths: 
2
Price Range:
$2,460 - $3,900
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$4,100
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$3,200
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$3,200
26
27
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30
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 $3,700
August 2026
SuMoTuWeThFrSaWeek
 1
$3,700
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3
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$4,100
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$4,100
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$4,100
23
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$3,910
30
31
 $3,660
September 2026
SuMoTuWeThFrSaWeek
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$3,660
6
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$3,660
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$3,660
20
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23
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25
26
$2,460
27
28
29
30
 
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7

Owner just reduced rates for available weeks in July - see calendar for adjusted rates

 

Owner will rent weekday to weekday the middle two weeks of July with a 7 night minimum to accommodate the need for auto ferry tickets if none available the weekend dates. 

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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
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$3,600
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$3,600
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25
$3,600
26
27
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29
30
31
 $3,600
August 2026
SuMoTuWeThFrSaWeek
 1
$3,600
2
3
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5
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7
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$3,600
9
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$3,600
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$3,600
23
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25
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28
29
$3,600
30
31
 $3,100
September 2026
SuMoTuWeThFrSaWeek
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2
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5
$3,100
6
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$2,800
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$2,800
20
21
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23
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25
26
$2,800
27
28
29
30
 $2,300
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Ferry Ticket Available for Purchase, 8/22 - 8/29  Car must be under 17 feet in length to use the owners ticket

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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 - $3,300
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
 1
2
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5
6
7
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9
10
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$3,200
12
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$3,200
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22
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24
25
$3,200
26
27
28
29
30
31
 $3,300
August 2026
SuMoTuWeThFrSaWeek
 1
$3,300
2
3
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5
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$3,300
9
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$3,300
16
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21
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$3,300
23
24
25
26
27
28
29
$2,900
30
31
 $2,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,000
6
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$2,000
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$2,000
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25
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$2,000
27
28
29
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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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 - $3,000
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
 1
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$5,250
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$5,250
19
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25
$5,250
26
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30
31
 $5,770
August 2026
SuMoTuWeThFrSaWeek
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$5,770
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$5,770
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$5,770
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$5,770
23
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$4,720
30
31
 $3,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
6
7
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10
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$3,000
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$3,000
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21
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25
26
$2,500
27
28
29
30
 $2,000
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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LODGJ

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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
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$3,000
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$3,000
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25
$3,000
26
27
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30
31
 $3,000
August 2026
SuMoTuWeThFrSaWeek
 1
$3,000
2
3
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5
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7
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$3,000
9
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$3,000
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$3,000
23
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$3,000
30
31
 $2,900
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,900
6
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$2,900
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$2,900
20
21
22
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25
26
27
28
29
30
 
Clean Fee: 
$360 per week
Tax: State & Local: 
11.7
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KOEOB

Inquire
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 - $2,500
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$3,800
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$3,800
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25
$3,800
26
27
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30
31
 $3,800
August 2026
SuMoTuWeThFrSaWeek
 1
$3,800
2
3
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5
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$4,500
9
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$4,500
16
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$4,500
23
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25
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27
28
29
$3,500
30
31
 $3,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,000
6
7
8
9
10
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12
$2,500
13
14
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$2,500
20
21
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23
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25
26
$2,500
27
28
29
30
 $2,500
Clean Fee: 
$275 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:
$0 - $0
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
 1
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$7,950
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$5,500
19
20
21
22
23
24
25
$7,950
26
27
28
29
30
31
 $7,950
August 2026
SuMoTuWeThFrSaWeek
 1
$7,950
2
3
4
5
6
7
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$7,950
9
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15
$7,950
16
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$7,950
23
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29
$5,500
30
31
 $7,950
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,950
6
7
8
9
10
11
12
$7,950
13
14
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18
19
$7,950
20
21
22
23
24
25
26
$7,950
27
28
29
30
 $7,950
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Owner reduced rates for weeks 7/12 & 8/23 by 20% - see calendar for adjusted rate

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ALLER

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Property Details
Oak Bluffs 4 Bedroom Home, Walk to Town & Beach!

10-minute walk to Oak Bluffs center and beach area from this lovely modern vacation home.  Enjoy all that the summer community of Oak Bluffs has to offer with quaint shops,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
 1
2
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5
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$5,250
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$5,250
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24
25
$5,250
26
27
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30
31
 $5,250
August 2026
SuMoTuWeThFrSaWeek
 1
$5,250
2
3
4
5
6
7
8
$6,000
9
10
11
12
13
14
15
$6,000
16
17
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$6,000
23
24
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28
29
$5,750
30
31
 $4,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,500
6
7
8
9
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12
$4,200
13
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$4,200
20
21
22
23
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25
26
$4,200
27
28
29
30
 $4,200
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
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KLEIB

Inquire
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:
$0 - $0
June 2026
SuMoTuWeThFrSa
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2
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27
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29
30
 
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
$4,070
12
13
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15
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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
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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
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PRIAN

Inquire
Property Details
Beautiful Upscale Contemporary Home, Designer Details Throughout, 4 Bedrooms, 4.5 Baths, Muliple Living Areas

Discover this stunning tri-level vacation home nestled in a peaceful community just on the outskirts of Oak Bluffs and minutes away from Oak Bluffs center, Edgartown Village, downtown Vineyard Haven, and several...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
4
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSa
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30
 
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
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$7,950
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$7,950
19
20
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29
30
31
 $8,250
August 2026
SuMoTuWeThFrSaWeek
 1
$8,250
2
3
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5
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7
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$8,500
9
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15
$8,500
16
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22
$8,500
23
24
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$8,250
30
31
 
September 2026
SuMoTuWeThFrSa
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29
30
 
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
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ROCHA

Inquire
Property Details
Bridle Path House, Quiet Lovely Neighborhood, Porch and Deck Areas, Large Yard, Central Location to all 3 Down Island Towns and Beaches

Lovely 3 bedroom 3 bath home sleeps 8, bordered by a large landscaped yard. The exterior features a shady wrap-around porch with rockers, a perfect place to relax, read a book,  and enjoy...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
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7
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9
10
11
$5,900
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18
$5,900
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24
25
$5,900
26
27
28
29
30
31
 $5,900
August 2026
SuMoTuWeThFrSaWeek
 1
$5,900
2
3
4
5
6
7
8
$6,500
9
10
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14
15
$6,500
16
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21
22
$6,500
23
24
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28
29
$6,500
30
31
 
September 2026
SuMoTuWeThFrSa
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20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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PETEO

Inquire
Property Details
Beautiful Custom Built Home Overlooking Little Duarte Pond, Beautifully Landscaped

Outstanding vacation home, centrally located to all three down-island town centers and multiple public beaches. This lovely home in a serene setting overlooks the picturesque Little Duarte Pond in the Iron Hill...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
5
Price Range:
$0 - $0
June 2026
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July 2026
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August 2026
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$8,500
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$8,500
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September 2026
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Clean Fee: 
$575 per week
Tax: State & Local: 
11.7
Add Favorite
 
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TRAVM

Inquire
Property Details
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:
$0 - $0
June 2026
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July 2026
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$5,350
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$5,350
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$5,350
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 $7,000
August 2026
SuMoTuWeThFrSaWeek
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$7,000
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$7,000
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$7,200
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$7,500
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September 2026
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
Add Favorite
 
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MAHAB

Inquire
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:
$0 - $0
June 2026
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July 2026
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$4,000
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$4,000
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$4,000
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 $4,000
August 2026
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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$4,000
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 $4,000
September 2026
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$3,500
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$3,500
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 $3,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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LANLL

Inquire
Property Details
Outstanding Waterfront Home & Guest House, Panoramic Views, Beach on the Lagoon, 5 Bedrooms, 4 Baths, AC

Gorgeous Expansive Waterfront Main & Guest Cottage, perfect for a multigenerational family vacation.  Spectacular views across and up the lagoon, this pristine home and guest cottage sits on just under two...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
5
Baths: 
4
Price Range:
$0 - $0
June 2026
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July 2026
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August 2026
SuMoTuWeThFrSaWeek
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$18,000
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$18,000
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$18,000
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$15,500
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 $15,500
September 2026
SuMoTuWeThFrSaWeek
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$15,500
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Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Two Week Minimum Stay Required per Owner

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