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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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:
$2,900 - $4,000
June 2024
SuMoTuWeThFrSaWeek
 1
$3,500
2
3
4
5
6
7
8
$3,500
9
10
11
12
13
14
15
$3,500
16
17
18
19
20
21
22
$3,500
23
24
25
26
27
28
29
$3,500
30
 $4,000
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
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
31
 $4,000
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$4,000
4
5
6
7
8
9
10
$4,000
11
12
13
14
15
16
17
$4,000
18
19
20
21
22
23
24
$4,000
25
26
27
28
29
30
31
$3,500
September 2024
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
$3,500
22
23
24
25
26
27
28
$3,500
29
30
 $3,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
 
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CAH48

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Classic Lovely Vineyard Cottage, Pristine Condition, Approximately 1.5 Miles to Town and Beaches. Mature Landscaped Yard, Spacious Deck

The Perfect Cozy Cottage, is pristinely maintained and situated in a quiet neighborhood just on the outskirts of Oak Bluffs.  This spacious 2 bedroom, 2 bath home sleeps 4. The...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,700 - $4,000
June 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
$2,700
9
10
11
12
13
14
15
$2,700
16
17
18
19
20
21
22
$2,700
23
24
25
26
27
28
29
$2,900
30
 $3,500
July 2024
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
31
 $4,000
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$4,000
4
5
6
7
8
9
10
$4,000
11
12
13
14
15
16
17
$4,000
18
19
20
21
22
23
24
$4,000
25
26
27
28
29
30
31
$4,000
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,700
8
9
10
11
12
13
14
$2,700
15
16
17
18
19
20
21
$2,700
22
23
24
25
26
27
28
$2,700
29
30
 
Clean Fee: 
$300, additional may apply multiple week rentals
Tax: State & Local: 
11.7
 
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ST304

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Sea View Condominium, Water View, Walk to town and beach

Sea View Condominium with a breathtaking view of Nantucket Sound from almost every room. Just steps from the beach.Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
2
Price Range:
$3,850 - $3,850
June 2024
SuMoTuWeThFrSaWeek
 1
$3,850
2
3
4
5
6
7
8
$2,700
9
10
11
12
13
14
15
$3,850
16
17
18
19
20
21
22
$3,850
23
24
25
26
27
28
29
$3,850
30
 $4,550
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,550
7
8
9
10
11
12
13
$4,550
14
15
16
17
18
19
20
$4,550
21
22
23
24
25
26
27
$4,550
28
29
30
31
 $5,070
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$5,070
4
5
6
7
8
9
10
$5,070
11
12
13
14
15
16
17
$5,070
18
19
20
21
22
23
24
$5,070
25
26
27
28
29
30
31
$5,070
September 2024
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
$3,850
22
23
24
25
26
27
28
$3,850
29
30
 
Clean Fee: 
$199 per week
Tax: State & Local: 
11.7
 
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KNOXA

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Modern Cottage, Recently Updated! Walk to Oak Bluffs Harbor and Town Center, 15 min walk

Walk to Oak Bluffs town center, ferry, or Inkwell Beach from this beach-chic recently renovated, adorable cottage! 

Upon entering you are greeted with an open floor plan in the living, kitchen,...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$3,000 - $3,800
June 2024
SuMoTuWeThFrSaWeek
 1
$3,150
2
3
4
5
6
7
8
$3,000
9
10
11
12
13
14
15
$3,000
16
17
18
19
20
21
22
$3,000
23
24
25
26
27
28
29
$3,000
30
 $3,800
July 2024
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
$3,600
28
29
30
31
 $3,800
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$3,800
4
5
6
7
8
9
10
$7,000
11
12
13
14
15
16
17
$7,000
18
19
20
21
22
23
24
$3,800
25
26
27
28
29
30
31
$3,800
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,800
8
9
10
11
12
13
14
$3,600
15
16
17
18
19
20
21
$3,600
22
23
24
25
26
27
28
$3,600
29
30
 $3,150
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7

Rates reduced for week of 8/18 - see calendar for adjusted rates

Ferry Tickets available for weeks 6/30-7/7, 7/7-7/14, 7/20-7/27 - please inquire

 
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KOEOB

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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 2024
SuMoTuWeThFrSaWeek
 1
$3,000
2
3
4
5
6
7
8
$2,500
9
10
11
12
13
14
15
$2,500
16
17
18
19
20
21
22
$2,700
23
24
25
26
27
28
29
$2,700
30
 $3,800
July 2024
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
31
 $3,800
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$3,800
4
5
6
7
8
9
10
$5,000
11
12
13
14
15
16
17
$4,500
18
19
20
21
22
23
24
$4,500
25
26
27
28
29
30
31
$3,500
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,000
8
9
10
11
12
13
14
$2,500
15
16
17
18
19
20
21
$2,500
22
23
24
25
26
27
28
$2,500
29
30
 $2,500
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
 
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MURPL

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Meadow View Farms House, Beautiful Tri- Level Contemporary Spacious Brick Patio Area, Private Landscaped Yard, Centrally Located

Beautiful Meadow View Farms home, bordered by an expansive landscaped yard, in a peaceful private setting. Association tennis courts are just a short distance from the house and Farm Neck Golf...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,400 - $3,580
June 2024
SuMoTuWeThFrSaWeek
 1
$3,400
2
3
4
5
6
7
8
$3,400
9
10
11
12
13
14
15
$3,580
16
17
18
19
20
21
22
$3,580
23
24
25
26
27
28
29
$5,680
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
$6,500
28
29
30
31
 $6,500
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$6,500
4
5
6
7
8
9
10
$6,700
11
12
13
14
15
16
17
$6,700
18
19
20
21
22
23
24
$6,500
25
26
27
28
29
30
31
$5,250
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,580
8
9
10
11
12
13
14
$3,580
15
16
17
18
19
20
21
$3,580
22
23
24
25
26
27
28
$3,580
29
30
 
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
 
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SACHE

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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:
$2,000 - $3,500
June 2024
SuMoTuWeThFrSaWeek
 1
$3,000
2
3
4
5
6
7
8
$3,500
9
10
11
12
13
14
15
$3,500
16
17
18
19
20
21
22
$3,500
23
24
25
26
27
28
29
$3,500
30
 $3,500
July 2024
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
31
 $3,500
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$3,500
4
5
6
7
8
9
10
$3,500
11
12
13
14
15
16
17
$3,500
18
19
20
21
22
23
24
$3,500
25
26
27
28
29
30
31
$3,500
September 2024
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
$3,500
22
23
24
25
26
27
28
$3,500
29
30
 $2,000
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
 
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FRANL

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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:
$2,000 - $3,300
June 2024
SuMoTuWeThFrSaWeek
 1
$2,000
2
3
4
5
6
7
8
$2,500
9
10
11
12
13
14
15
$2,500
16
17
18
19
20
21
22
$2,500
23
24
25
26
27
28
29
$3,300
30
 $3,300
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,300
7
8
9
10
11
12
13
$3,300
14
15
16
17
18
19
20
$3,300
21
22
23
24
25
26
27
$3,300
28
29
30
31
 $3,300
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$3,300
4
5
6
7
8
9
10
$3,300
11
12
13
14
15
16
17
$3,300
18
19
20
21
22
23
24
$3,300
25
26
27
28
29
30
31
$3,000
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,500
8
9
10
11
12
13
14
$2,500
15
16
17
18
19
20
21
$2,500
22
23
24
25
26
27
28
$2,500
29
30
 $2,000
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
 
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GOLLB

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

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

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
3
Baths: 
1
Price Range:
$1,850 - $3,200
June 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
$2,200
16
17
18
19
20
21
22
$2,600
23
24
25
26
27
28
29
$2,800
30
 $3,100
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,100
7
8
9
10
11
12
13
$3,100
14
15
16
17
18
19
20
$3,100
21
22
23
24
25
26
27
$3,100
28
29
30
31
 $3,200
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$3,200
4
5
6
7
8
9
10
$3,200
11
12
13
14
15
16
17
$3,200
18
19
20
21
22
23
24
$3,200
25
26
27
28
29
30
31
$2,800
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$1,900
8
9
10
11
12
13
14
$1,900
15
16
17
18
19
20
21
$1,900
22
23
24
25
26
27
28
$1,900
29
30
 $1,850
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7

Cottage books Tuesday to Tuesday July & August weeks

 
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PETEO

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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:
$3,000 - $3,000
June 2024
SuMoTuWeThFrSaWeek
 1
$3,400
2
3
4
5
6
7
8
$3,500
9
10
11
12
13
14
15
$3,500
16
17
18
19
20
21
22
$3,900
23
24
25
26
27
28
29
$5,600
30
 $6,200
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,200
7
8
9
10
11
12
13
$6,200
14
15
16
17
18
19
20
$6,200
21
22
23
24
25
26
27
$6,700
28
29
30
31
 $7,200
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$7,200
4
5
6
7
8
9
10
$7,200
11
12
13
14
15
16
17
$7,200
18
19
20
21
22
23
24
$7,200
25
26
27
28
29
30
31
$6,100
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,900
8
9
10
11
12
13
14
$3,400
15
16
17
18
19
20
21
$3,400
22
23
24
25
26
27
28
$3,400
29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
 
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LODGJ

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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 2024
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
28
29
$2,900
30
 $2,900
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,900
7
8
9
10
11
12
13
$2,900
14
15
16
17
18
19
20
$2,900
21
22
23
24
25
26
27
$2,900
28
29
30
31
 $2,900
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$2,900
4
5
6
7
8
9
10
$2,900
11
12
13
14
15
16
17
$2,900
18
19
20
21
22
23
24
$2,900
25
26
27
28
29
30
31
$2,900
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,900
8
9
10
11
12
13
14
$2,900
15
16
17
18
19
20
21
$2,900
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$360 per week
Tax: State & Local: 
11.7
 
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ADELM

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Waterfront Lagoon, Deck with Gorgeous Sunset Views, WiFi

Adorable waterfront cottage, pristinely maintained throughout the years.  Enjoy privacy and and gorgeous water views of the lagoon from the spacious deck.  Wade across the generally ankle deep inlet in...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$1,900 - $2,850
June 2024
SuMoTuWeThFrSaWeek
 1
$1,900
2
3
4
5
6
7
8
$1,900
9
10
11
12
13
14
15
$1,900
16
17
18
19
20
21
22
$2,180
23
24
25
26
27
28
29
$2,850
30
 
July 2024
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
28
29
30
31
 $3,050
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$3,050
4
5
6
7
8
9
10
$3,050
11
12
13
14
15
16
17
$3,050
18
19
20
21
22
23
24
$3,050
25
26
27
28
29
30
31
$2,270
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$1,950
8
9
10
11
12
13
14
$1,950
15
16
17
18
19
20
21
$1,950
22
23
24
25
26
27
28
$1,950
29
30
 $1,950
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
aburbs-01-exterior.jpg
 
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BURBS

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Set Just on the ouskirts of Oak Bluffs. Central AC, Screened Porch

Lovely spacious 3+ bedroom, 3.5 bedroom home within a mile from Oak Bluffs center and beach area.  Fully furnished screen porch and shady porch.  This lovely home sleeps families of 8 comfortably.

The main...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$0 - $0
June 2024
SuMoTuWeThFrSa
 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
28
29
30
 
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
$5,500
21
22
23
24
25
26
27
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
$6,000
18
19
20
21
22
23
24
25
26
27
28
29
30
31
September 2024
SuMoTuWeThFrSa
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
28
29
30
 
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
 
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LONGK

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Bayes Hill Beauty - Central A/C, Wifi, Association Tennis, Bose Soundock II
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$0 - $0
June 2024
SuMoTuWeThFrSaWeek
 1
$2,500
2
3
4
5
6
7
8
$2,750
9
10
11
12
13
14
15
$2,750
16
17
18
19
20
21
22
$3,000
23
24
25
26
27
28
29
$3,000
30
 $3,500
July 2024
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
31
 $4,000
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$4,000
4
5
6
7
8
9
10
$4,000
11
12
13
14
15
16
17
$4,000
18
19
20
21
22
23
24
$4,000
25
26
27
28
29
30
31
$3,750
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,250
8
9
10
11
12
13
14
$3,000
15
16
17
18
19
20
21
$3,000
22
23
24
25
26
27
28
$2,500
29
30
 $2,500
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
 
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ROCHA

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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 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 the...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$0 - $0
June 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
$5,100
16
17
18
19
20
21
22
$5,100
23
24
25
26
27
28
29
$5,900
30
 $5,900
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,900
7
8
9
10
11
12
13
$5,900
14
15
16
17
18
19
20
$5,900
21
22
23
24
25
26
27
$5,900
28
29
30
31
 $5,900
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$5,900
4
5
6
7
8
9
10
$5,900
11
12
13
14
15
16
17
$5,900
18
19
20
21
22
23
24
$5,900
25
26
27
28
29
30
31
September 2024
SuMoTuWeThFrSa
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
28
29
30
 
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7

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