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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Bayes Hill Beauty - Stunning Landscaping, Privately Situated Deck & Patio Association Tennis, Bose Soundock II
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$5,000 - $6,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
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20
21
$5,000
22
23
24
25
26
27
28
$5,000
29
30
 $6,300
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,300
6
7
8
9
10
11
12
$6,300
13
14
15
16
17
18
19
$6,300
20
21
22
23
24
25
26
$6,300
27
28
29
30
31
 $6,300
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,300
3
4
5
6
7
8
9
$7,200
10
11
12
13
14
15
16
$7,200
17
18
19
20
21
22
23
$7,200
24
25
26
27
28
29
30
$6,000
31
 $6,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,000
7
8
9
10
11
12
13
$6,000
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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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:
$540 - $6,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$3,700
22
23
24
25
26
27
28
$3,900
29
30
 $5,250
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,250
6
7
8
9
10
11
12
$4,000
13
14
15
16
17
18
19
$5,250
20
21
22
23
24
25
26
$5,250
27
28
29
30
31
 $5,250
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,250
3
4
5
6
7
8
9
$6,000
10
11
12
13
14
15
16
$6,000
17
18
19
20
21
22
23
$6,000
24
25
26
27
28
29
30
$5,750
31
 $4,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,500
7
8
9
10
11
12
13
$4,200
14
15
16
17
18
19
20
$4,200
21
22
23
24
25
26
27
$4,200
28
29
30
 
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
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DAWKN

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Property Details
Exquisite Designer Home, 10 minute Walk to Oak Bluffs Town Center, Screened Porch, Patio Dining Area, Landscaped Yard, Professionally Decorated, AC

Quietly nestled on a quiet street just on the outskirts of town, this brightly lit home features a mix of coastal details and traditionally styled upscale furnishings for your comfort. The...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$5,100 - $6,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$5,300
22
23
24
25
26
27
28
$5,400
29
30
 $6,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,000
6
7
8
9
10
11
12
$6,000
13
14
15
16
17
18
19
$6,000
20
21
22
23
24
25
26
$6,000
27
28
29
30
31
 $6,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,000
3
4
5
6
7
8
9
$6,000
10
11
12
13
14
15
16
$6,000
17
18
19
20
21
22
23
$6,000
24
25
26
27
28
29
30
$6,000
31
 $6,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,000
7
8
9
10
11
12
13
$5,100
14
15
16
17
18
19
20
$5,100
21
22
23
24
25
26
27
$5,100
28
29
30
 $5,100
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
Add Favorite
 
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BOOND

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Property Details
Wonderful Vacation Home, East Chop Area of Oak Bluffs, Private Yard, Screened Porch, 4 bedrooms, 2 baths.

Nestled on a quiet street in the idyllic East Chop area of Oak Bluffs, this classic New England summer home offers vacationing families and friends a special place to gather...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,200 - $6,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$4,200
22
23
24
25
26
27
28
$4,200
29
30
 $5,200
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,200
6
7
8
9
10
11
12
$5,200
13
14
15
16
17
18
19
$5,500
20
21
22
23
24
25
26
$5,500
27
28
29
30
31
 $6,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,000
3
4
5
6
7
8
9
$6,000
10
11
12
13
14
15
16
$6,500
17
18
19
20
21
22
23
$6,500
24
25
26
27
28
29
30
$6,000
31
 $6,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,000
7
8
9
10
11
12
13
$5,000
14
15
16
17
18
19
20
$5,000
21
22
23
24
25
26
27
$5,000
28
29
30
 $5,000
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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CENCR

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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:
$3,000 - $5,800
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,000
29
30
 $4,800
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,800
6
7
8
9
10
11
12
$4,800
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$5,200
27
28
29
30
31
 $5,800
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,800
3
4
5
6
7
8
9
$8,800
10
11
12
13
14
15
16
$11,800
17
18
19
20
21
22
23
$11,800
24
25
26
27
28
29
30
$5,800
31
 $4,000
September 2025
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
$3,500
21
22
23
24
25
26
27
$3,000
28
29
30
 $3,000
Clean Fee: 
$480 per week
Tax: State & Local: 
11.7

Rates just reduced on available weeks - see calendar for adjusted rates

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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 - $5,700
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$3,000
22
23
24
25
26
27
28
$3,600
29
30
 $4,200
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,200
6
7
8
9
10
11
12
$4,200
13
14
15
16
17
18
19
$4,200
20
21
22
23
24
25
26
$4,200
27
28
29
30
31
 $4,200
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,200
3
4
5
6
7
8
9
$5,000
10
11
12
13
14
15
16
$5,700
17
18
19
20
21
22
23
$5,000
24
25
26
27
28
29
30
$5,000
31
 $4,900
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,900
7
8
9
10
11
12
13
$3,000
14
15
16
17
18
19
20
$3,000
21
22
23
24
25
26
27
$3,000
28
29
30
 $2,300
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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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:
$3,750 - $5,600
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$4,350
22
23
24
25
26
27
28
$4,600
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
16
17
18
19
$5,600
20
21
22
23
24
25
26
$5,600
27
28
29
30
31
 $5,600
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,600
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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HAZAM

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Property Details
The Retreat at Towanticut Where Coastal Elegance Meets Island Serenity, 3 Bedrooms, 2 Baths, Landscaped Yard, Deck Dining Area

Welcome to The Retreat at Towanticut— a chic coastal escape where upscale comfort meets effortless Vineyard charm. Nestled in the heart of Oak Bluffs and just a 15-minute stroll to Circuit Avenue...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$3,000 - $5,600
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$4,400
22
23
24
25
26
27
28
$4,400
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
16
17
18
19
$5,600
20
21
22
23
24
25
26
$5,600
27
28
29
30
31
 $5,600
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,600
3
4
5
6
7
8
9
$6,400
10
11
12
13
14
15
16
$6,400
17
18
19
20
21
22
23
$6,400
24
25
26
27
28
29
30
$6,000
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
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
 $3,000
Clean Fee: 
$350
Tax: State & Local: 
11.7
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WESTW

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Property Details
Tri Level Oak Bluffs Home, Central A/C, Set in Private Community of Sengekontacket, Multiple Living Spaces, Large Deck, Patio Area, Association Tennis

Privately situated on a hilltop in Sengekontacket, -spacious tri-level, 4000 sq ft contemporary home. Set in a wonderful, family friendly community, offering association tennis courts, and an association dock on Sengekontacket Pond...Read more

Location: 
Oak Bluffs
Sleeps: 
14
Bedrooms: 
5
Baths: 
2
Price Range:
$5,000 - $5,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$6,500
22
23
24
25
26
27
28
$7,500
29
30
 $8,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,000
6
7
8
9
10
11
12
$9,000
13
14
15
16
17
18
19
$9,000
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
$12,000
10
11
12
13
14
15
16
$12,000
17
18
19
20
21
22
23
$12,000
24
25
26
27
28
29
30
$8,500
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
$5,500
21
22
23
24
25
26
27
$5,000
28
29
30
 $5,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
Add Favorite
 
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ARMSA

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Property Details
Cozy Newly updated Seashore Cottage, East Chop Highlands Area, Farmers Porch and Deck

If you are looking for an immaculate, charming, cottage-style, yet modern home close to Oak Bluffs center, look no further. This recently updated 3 bedroom, 2 bath home features sunny open...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,500 - $5,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$5,500
22
23
24
25
26
27
28
$5,500
29
30
 
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
$5,500
20
21
22
23
24
25
26
$5,500
27
28
29
30
31
 
August 2025
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
 $5,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,500
7
8
9
10
11
12
13
$5,500
14
15
16
17
18
19
20
$5,500
21
22
23
24
25
26
27
$5,500
28
29
30
 $3,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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ROS22

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Property Details

Set in the heart of Oak Bluffs and on a quiet residential street, this newly updated tastefully decorated vacation home offers rental guests all the comforts of home inside and out....Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
1
Price Range:
$3,000 - $5,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,000
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
16
17
18
19
$5,000
20
21
22
23
24
25
26
$5,000
27
28
29
30
31
 $5,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,500
3
4
5
6
7
8
9
$5,500
10
11
12
13
14
15
16
$5,500
17
18
19
20
21
22
23
$5,500
24
25
26
27
28
29
30
$5,500
31
 $4,000
September 2025
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
 $3,000
Clean Fee: 
$350 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 - $5,250
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,720
29
30
 $5,250
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,250
6
7
8
9
10
11
12
$5,250
13
14
15
16
17
18
19
$5,250
20
21
22
23
24
25
26
$5,250
27
28
29
30
31
 $5,770
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,770
3
4
5
6
7
8
9
$5,770
10
11
12
13
14
15
16
$5,770
17
18
19
20
21
22
23
$5,770
24
25
26
27
28
29
30
$4,720
31
 $3,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,500
7
8
9
10
11
12
13
$3,000
14
15
16
17
18
19
20
$3,000
21
22
23
24
25
26
27
$2,500
28
29
30
 $2,000
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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TOTHG

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Property Details
Adorable Updated Vineyard Cottage, Lovely Landscaped Yard, Central A/C, Flat Screen TV, Bike Paths at end of Drive, One Mile to Oak Bluffs Center

Bright and classic summer cottage. Conveniently located just one mile from Oak Bluffs town center, Inkwell Beach, shops, fine and family dining, historic Flying Horses Carousel, public tennis courts, Ocean...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$4,950 - $4,950
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$4,950
22
23
24
25
26
27
28
$4,950
29
30
 $4,950
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,950
6
7
8
9
10
11
12
$4,950
13
14
15
16
17
18
19
$4,950
20
21
22
23
24
25
26
$4,950
27
28
29
30
31
 $4,950
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,950
3
4
5
6
7
8
9
$4,950
10
11
12
13
14
15
16
$4,950
17
18
19
20
21
22
23
$4,950
24
25
26
27
28
29
30
$4,950
31
 $4,950
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,950
7
8
9
10
11
12
13
$4,950
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
Add Favorite
 
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TAYLJ

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Property Details
SPACIOUS LIGHTFILLED 3 BEDROOM, 3 BATH HOME, PRIVATE DECK WITH PATIO DINING, LOCATED IN QUIET COMMUNITY OF HOMES

Enjoy the best of the Island—the serenity of a secluded wooded sanctuary, the convenience, fun and shopping of the 3 Down Island towns (Oak Bluffs, Edgartown and Vineyard Haven), and easy access...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$4,000 - $4,900
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,000
29
30
 $4,100
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,100
6
7
8
9
10
11
12
$4,100
13
14
15
16
17
18
19
$4,100
20
21
22
23
24
25
26
$4,100
27
28
29
30
31
 $4,900
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,900
3
4
5
6
7
8
9
$5,100
10
11
12
13
14
15
16
$5,100
17
18
19
20
21
22
23
$5,100
24
25
26
27
28
29
30
$4,900
31
 $4,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,500
7
8
9
10
11
12
13
$4,500
14
15
16
17
18
19
20
$4,000
21
22
23
24
25
26
27
$4,000
28
29
30
 $4,000
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

 

 

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GLOVL

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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 2025
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
 $4,700
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,700
6
7
8
9
10
11
12
$4,700
13
14
15
16
17
18
19
$4,700
20
21
22
23
24
25
26
$4,700
27
28
29
30
31
 $4,900
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,900
3
4
5
6
7
8
9
$4,900
10
11
12
13
14
15
16
$4,900
17
18
19
20
21
22
23
$4,900
24
25
26
27
28
29
30
$4,900
31
 
September 2025
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: 
$350 per week
Tax: State & Local: 
11.7

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