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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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 - $6,000
June 2026
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
 $5,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,000
5
6
7
8
9
10
11
$5,000
12
13
14
15
16
17
18
$5,000
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
31
 $5,500
August 2026
SuMoTuWeThFrSaWeek
 1
$5,500
2
3
4
5
6
7
8
$6,000
9
10
11
12
13
14
15
$5,500
16
17
18
19
20
21
22
$6,000
23
24
25
26
27
28
29
$6,000
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
$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
 $3,000
Clean Fee: 
$380 per week
Tax: State & Local: 
11.7
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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:
$4,000 - $6,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
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
 $5,200
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,200
5
6
7
8
9
10
11
$5,200
12
13
14
15
16
17
18
$5,500
19
20
21
22
23
24
25
$5,500
26
27
28
29
30
31
 $6,000
August 2026
SuMoTuWeThFrSaWeek
 1
$6,000
2
3
4
5
6
7
8
$6,500
9
10
11
12
13
14
15
$6,500
16
17
18
19
20
21
22
$6,500
23
24
25
26
27
28
29
$6,000
30
31
 $5,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
8
9
10
11
12
$5,000
13
14
15
16
17
18
19
$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
 $4,000
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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GOLDF

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Property Details
Outstanding Oak Bluffs Summer Home with Heated Pool and Patio Surround, Screened Porch with Living and Dining Area, Association Tennis Courts.

MVVR Exclusive Listing:  Set in a quiet community of homes just on the outskirts of OB, this outstanding home provides a peaceful getaway yet is just a short drive to the...Read more

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

Pool Heated to 80 July & August and the 1st week in September included in the rental rate!

 

Pool Heated to 80  May, June & September weeks at additional cost ($400). 

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DENAL

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

Weekly rates reduced by $500 per week for available weeks in May, June & July

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

 

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BRANF

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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 - $5,400
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,400
7
8
9
10
11
12
13
$5,400
14
15
16
17
18
19
20
$5,400
21
22
23
24
25
26
27
$5,400
28
29
30
 $6,300
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,300
5
6
7
8
9
10
11
$6,300
12
13
14
15
16
17
18
$6,500
19
20
21
22
23
24
25
$6,700
26
27
28
29
30
31
 $6,900
August 2026
SuMoTuWeThFrSaWeek
 1
$6,900
2
3
4
5
6
7
8
$9,100
9
10
11
12
13
14
15
$13,500
16
17
18
19
20
21
22
$9,500
23
24
25
26
27
28
29
$6,900
30
31
 $6,600
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,600
6
7
8
9
10
11
12
$5,900
13
14
15
16
17
18
19
$5,000
20
21
22
23
24
25
26
$5,000
27
28
29
30
 $5,000
Clean Fee: 
$500 per week ($375 for interim cleaning on multiple week rentals)
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 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
$4,000
21
22
23
24
25
26
27
$4,720
28
29
30
 $5,250
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,250
5
6
7
8
9
10
11
$5,250
12
13
14
15
16
17
18
$5,250
19
20
21
22
23
24
25
$5,250
26
27
28
29
30
31
 $5,770
August 2026
SuMoTuWeThFrSaWeek
 1
$5,770
2
3
4
5
6
7
8
$5,770
9
10
11
12
13
14
15
$5,770
16
17
18
19
20
21
22
$5,770
23
24
25
26
27
28
29
$4,720
30
31
 $3,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
6
7
8
9
10
11
12
$3,000
13
14
15
16
17
18
19
$3,000
20
21
22
23
24
25
26
$2,500
27
28
29
30
 $2,000
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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ROCHA

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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:
$5,100 - $5,100
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
$5,100
14
15
16
17
18
19
20
21
22
23
24
25
26
27
$5,900
28
29
30
 $5,900
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,900
5
6
7
8
9
10
11
$5,900
12
13
14
15
16
17
18
$5,900
19
20
21
22
23
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
11
12
13
14
15
$6,500
16
17
18
19
20
21
22
$6,500
23
24
25
26
27
28
29
$6,500
30
31
 
September 2026
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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VANAL

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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:
$3,000 - $5,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
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
$3,500
28
29
30
 $5,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,000
5
6
7
8
9
10
11
$5,000
12
13
14
15
16
17
18
$4,000
19
20
21
22
23
24
25
$4,000
26
27
28
29
30
31
 $5,000
August 2026
SuMoTuWeThFrSaWeek
 1
$5,000
2
3
4
5
6
7
8
$7,500
9
10
11
12
13
14
15
$7,500
16
17
18
19
20
21
22
$7,500
23
24
25
26
27
28
29
$5,000
30
31
 $4,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,500
6
7
8
9
10
11
12
$4,500
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: 
$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

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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 - $5,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,000
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
 $4,800
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,800
5
6
7
8
9
10
11
$4,800
12
13
14
15
16
17
18
$4,800
19
20
21
22
23
24
25
$4,800
26
27
28
29
30
31
 
August 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
$10,500
9
10
11
12
13
14
15
$11,800
16
17
18
19
20
21
22
$11,800
23
24
25
26
27
28
29
$6,200
30
31
 $5,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
8
9
10
11
12
$4,000
13
14
15
16
17
18
19
$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
 $4,000
Clean Fee: 
$480 per week
Tax: State & Local: 
11.7
Add Favorite
 
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WILCM

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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:
$70 - $5,000
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
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
$4,500
19
20
21
22
23
24
25
$4,000
26
27
28
29
30
31
 $5,000
August 2026
SuMoTuWeThFrSaWeek
 1
$5,000
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
$5,000
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
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

Ferry Tickets for Purchase, 7/26- 8/2 & 8/23- 8/30  Please inquire! 

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HANRJ

(0)Inquire/Share
Property Details
Spacious Oak Bluffs Contemporary Home, 4 Bedrooms & 4 Baths, Quiet Private Location in Bayes Hill Community of Homes

Privately situated on the outskirts of Oak Bluffs, yet centrally located to towns and beaches. The home features a large patio area with outdoor dining and grill area and a spacious...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$3,500 - $5,000
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
$3,800
28
29
30
 $5,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,000
5
6
7
8
9
10
11
$5,000
12
13
14
15
16
17
18
$5,000
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
31
 $6,000
August 2026
SuMoTuWeThFrSaWeek
 1
$6,000
2
3
4
5
6
7
8
$7,000
9
10
11
12
13
14
15
$7,000
16
17
18
19
20
21
22
$7,000
23
24
25
26
27
28
29
$5,500
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
$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
 $3,500
Clean Fee: 
$575
Tax: State & Local: 
11.7

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

 

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JOHNL

(0)Inquire/Share
Property Details
"Endless Summer Vacation" Stylish, Newly Updated 3 + Bedroom, Sleeps 8, East Chop Area of Oak Bluffs, Deck Living & Dining Area, Screened Porch
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$3,500 - $5,000
June 2026
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
 $5,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,000
5
6
7
8
9
10
11
$5,000
12
13
14
15
16
17
18
$5,000
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
31
 $5,500
August 2026
SuMoTuWeThFrSaWeek
 1
$5,500
2
3
4
5
6
7
8
$7,500
9
10
11
12
13
14
15
$7,500
16
17
18
19
20
21
22
$7,500
23
24
25
26
27
28
29
$7,500
30
31
 $5,000
September 2026
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
 $5,000
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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DUREJ

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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:
$70 - $5,000
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
 $5,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,500
5
6
7
8
9
10
11
$5,000
12
13
14
15
16
17
18
$5,000
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
31
 $5,500
August 2026
SuMoTuWeThFrSaWeek
 1
$5,500
2
3
4
5
6
7
8
$6,000
9
10
11
12
13
14
15
$6,000
16
17
18
19
20
21
22
$5,750
23
24
25
26
27
28
29
$5,000
30
31
 $4,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
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: 
$400 per week
Tax: State & Local: 
11.7
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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 2026
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
 
July 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
28
29
30
31
 $4,950
August 2026
SuMoTuWeThFrSaWeek
 1
$4,950
2
3
4
5
6
7
8
$4,950
9
10
11
12
13
14
15
$4,950
16
17
18
19
20
21
22
$4,950
23
24
25
26
27
28
29
$4,950
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
$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
 $4,000
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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GLOVL

(0)Inquire/Share
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 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
28
29
30
 $4,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,700
5
6
7
8
9
10
11
$4,700
12
13
14
15
16
17
18
$4,700
19
20
21
22
23
24
25
$4,700
26
27
28
29
30
31
 $4,900
August 2026
SuMoTuWeThFrSaWeek
 1
$4,900
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
 
September 2026
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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