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Newly refurbished Tri Level, Gorgeous Water Views of North Shore in Exclusive Makonikey Area

Stunning Hilltop Post & Beam Vacation Home with a relaxed coastal ambiance and picturesque distant water vistas! Nestled off Lambert’s Cove Rd in Vineyard Haven, this exquisite property resides within...Read more

Location: 
Vineyard Haven
Sleeps: 
9
Bedrooms: 
4
Baths: 
3
Price Range:
$5,000 - $12,000
June 2026
SuMoTuWeThFrSaWeek
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$5,800
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$5,800
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$6,800
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$8,990
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 $11,000
July 2026
SuMoTuWeThFrSaWeek
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$11,000
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$11,000
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$11,000
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$12,000
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 $12,000
August 2026
SuMoTuWeThFrSaWeek
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$12,000
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$12,000
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$12,000
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$12,000
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$10,000
30
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 $7,000
September 2026
SuMoTuWeThFrSaWeek
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$7,000
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$6,500
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$6,500
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$6,500
27
28
29
30
 $5,000
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

 

 

 

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COS67

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Property Details
Beautiful 3 Bedroom, 3.5 bath Home, Bluestone Patio with Outdoor Dining & Grill , Lovely Landscaped Yard. Situated on Quiet Street, Walk to Town
Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
3
Baths: 
3
Price Range:
$6,000 - $12,000
June 2026
SuMoTuWeThFrSaWeek
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$6,000
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$6,000
14
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$6,000
21
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27
$6,000
28
29
30
 $8,200
July 2026
SuMoTuWeThFrSaWeek
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2
3
4
$8,200
5
6
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10
11
$8,200
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$8,200
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25
$8,200
26
27
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30
31
 $8,200
August 2026
SuMoTuWeThFrSaWeek
 1
$8,200
2
3
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5
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8
$12,000
9
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$12,000
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$12,000
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$8,200
30
31
 $6,000
September 2026
SuMoTuWeThFrSaWeek
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$6,000
6
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$6,000
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$6,000
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21
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26
$6,000
27
28
29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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EW138

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Property Details
Beautiful Oak Bluffs Home, 20 x 40 Heated Pool, 6 Bedrooms, 4 baths, Sleeps 14, Screened Porch, Multiple Living Spaces

Oak Bluffs vacation retreat with multiple indoor, and outdoor living and entertaining areas. The highlight of this spacious summer home is the heated Gunite pool with waterfall, bluestone patio, and...Read more

Location: 
Oak Bluffs
Sleeps: 
14
Bedrooms: 
6
Baths: 
4
Price Range:
$9,100 - $12,000
June 2026
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July 2026
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August 2026
SuMoTuWeThFrSa
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September 2026
SuMoTuWeThFrSa
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Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

Pool Heated to 82 included in rental rate July and August, Spa in pool is heated to same the temperature as pool.

 

Additional Spa Heat 6 to 10pm, $250 per week. Available upon request. 

 

Pool Heated to 82 June & Sept additional $275 per week. May & October additional $350 per week. 

 

Firepit seen in photos is not for renter use. 

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SHAJO

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Property Details

Step into this exquisite Victorian-style residence, meticulously renovated to preserve its original allure while offering a sanctuary away from the bustle of everyday life. Nestled in the picturesque town of...Read more

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

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Property Details
Beautiful Newly Renovated Katama Area Home. Multiple Indoor, Outdoor Living Spaces, Sleeps 8.

Nestled within the scenic Katama area of Edgartown, this home boasts a spacious layout and exquisite renovations, complemented by professional decor. Its prime location offers easy access to both Edgartown...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,500 - $12,000
June 2026
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
$5,000
21
22
23
24
25
26
27
$6,500
28
29
30
 $8,800
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,800
5
6
7
8
9
10
11
$6,500
12
13
14
15
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17
18
$7,000
19
20
21
22
23
24
25
$7,500
26
27
28
29
30
31
 $8,000
August 2026
SuMoTuWeThFrSaWeek
 1
$8,000
2
3
4
5
6
7
8
$12,000
9
10
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13
14
15
$12,000
16
17
18
19
20
21
22
$10,000
23
24
25
26
27
28
29
$8,500
30
31
 $6,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,500
6
7
8
9
10
11
12
$6,000
13
14
15
16
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18
19
$6,000
20
21
22
23
24
25
26
$6,000
27
28
29
30
 $4,500
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

 

 

 

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POWDA

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Property Details
Beautiful Newly Updated Oak Bluffs Home, Nestled on a Large Landscaped Lot in a Quiet Enclave of Homes. 4 Bedrooms. 4.5 Baths

Step inside to discover a welcoming interior, highlighted by a sunroom featuring comfortable seating around the TV. The open first-floor plan seamlessly integrates the main family room complete with a media...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,000 - $12,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,000
7
8
9
10
11
12
13
$6,500
14
15
16
17
18
19
20
$7,000
21
22
23
24
25
26
27
$7,500
28
29
30
 $8,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,500
5
6
7
8
9
10
11
$8,500
12
13
14
15
16
17
18
$8,500
19
20
21
22
23
24
25
$9,000
26
27
28
29
30
31
 $9,000
August 2026
SuMoTuWeThFrSaWeek
 1
$9,000
2
3
4
5
6
7
8
$12,000
9
10
11
12
13
14
15
$12,000
16
17
18
19
20
21
22
$11,500
23
24
25
26
27
28
29
$9,000
30
31
 $7,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,000
6
7
8
9
10
11
12
$6,000
13
14
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18
19
$6,000
20
21
22
23
24
25
26
$6,000
27
28
29
30
 $6,000
Clean Fee: 
$600 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 - $11,800
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
 $5,800
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,800
5
6
7
8
9
10
11
$5,800
12
13
14
15
16
17
18
$6,200
19
20
21
22
23
24
25
$6,200
26
27
28
29
30
31
 $6,200
August 2026
SuMoTuWeThFrSaWeek
 1
$6,200
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
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PIN15

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Property Details
Beautiful Oak Bluffs Home, Screened Porch & Open Porch, Association Tennis Courts, 4 bedrooms, 3.5 baths, Ideally Located just 2 miles to Town and Beach

Spacious contemporary home nestled in the lovely community of homes Meadow View Farms just on the outskirts of Oak Bluffs and 2 miles to town center and Oak Bluffs beaches....Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,820 - $11,750
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$9,750
7
8
9
10
11
12
13
$9,750
14
15
16
17
18
19
20
$9,750
21
22
23
24
25
26
27
$9,750
28
29
30
 $11,750
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,750
5
6
7
8
9
10
11
$11,750
12
13
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18
$11,750
19
20
21
22
23
24
25
$11,750
26
27
28
29
30
31
 $11,750
August 2026
SuMoTuWeThFrSaWeek
 1
$11,750
2
3
4
5
6
7
8
$11,750
9
10
11
12
13
14
15
$11,750
16
17
18
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21
22
$11,750
23
24
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27
28
29
$11,750
30
31
 $11,750
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$11,750
6
7
8
9
10
11
12
$9,750
13
14
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19
$9,750
20
21
22
23
24
25
26
$9,750
27
28
29
30
 $9,750
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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PANDC

(0)Inquire/Share
Property Details
Coffin's Field, Main House, and Guest Apartment above Garage, Heated Pool - 16 x 32, Porch and Spacious Deck, 8 Minute Drive to Gorgeous Trustees / Long Point Beach

Lovely farmhouse-style 5-bedroom home with heated pool -16' x 32', 3 to 5 feet depth,  main house, and guest apartment over the garage centrally located and easily accessible to Long Point Beach and Edgartown...Read more

Location: 
Edgartown
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$6,000 - $11,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,500
7
8
9
10
11
12
13
$8,950
14
15
16
17
18
19
20
$8,950
21
22
23
24
25
26
27
$8,950
28
29
30
 $10,800
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$10,800
5
6
7
8
9
10
11
$10,800
12
13
14
15
16
17
18
$10,800
19
20
21
22
23
24
25
$10,800
26
27
28
29
30
31
 $10,800
August 2026
SuMoTuWeThFrSaWeek
 1
$10,800
2
3
4
5
6
7
8
$12,900
9
10
11
12
13
14
15
$12,900
16
17
18
19
20
21
22
$12,900
23
24
25
26
27
28
29
$11,500
30
31
 $8,950
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,950
6
7
8
9
10
11
12
$8,950
13
14
15
16
17
18
19
$8,500
20
21
22
23
24
25
26
$8,500
27
28
29
30
 $6,000
Clean Fee: 
$675
Tax: State & Local: 
11.7

Pool & the Spa in the pool heated to 81 degrees, included in Rental Rate July & August Weeks. Spa not heated to higher temperatures and jets will be off. 

 

Pool & Spa  Heated to 81 degrees June & September weeks additional $300 propane surcharge per week. 

 

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JOSEJ

(0)Inquire/Share
Property Details
Exquisite Coastal Style Home, Pool, Patio, Landscaped Yard! 10 minute walk to Oak Bluffs Center, Luxury Interior, 3 bedrooms, 4 baths, Multiple Living Spaces

This newly constructed, luxurious home offers the perfect blend of comfort, style, and convenience. Featuring a heated 16 x 32' pool with varying depths of 3 to 8 feet, a...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,000 - $11,500
June 2026
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
$6,000
21
22
23
24
25
26
27
$6,000
28
29
30
 $11,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,500
5
6
7
8
9
10
11
$11,500
12
13
14
15
16
17
18
$11,500
19
20
21
22
23
24
25
$11,500
26
27
28
29
30
31
 $11,500
August 2026
SuMoTuWeThFrSaWeek
 1
$11,500
2
3
4
5
6
7
8
$13,000
9
10
11
12
13
14
15
$13,000
16
17
18
19
20
21
22
$13,000
23
24
25
26
27
28
29
$11,500
30
31
 $11,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$11,500
6
7
8
9
10
11
12
$7,000
13
14
15
16
17
18
19
$6,000
20
21
22
23
24
25
26
$6,000
27
28
29
30
 $6,500
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

Pool Heated to  81 degrees included in rental rate last Sat in June to first Sat in September. Pool Depth 3 feet to 8 Feet 

Pool Heated to 81 degrees June and September weeks additional $275 per week  

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INGAE

(0)Inquire/Share
Property Details
Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$4,630 - $11,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,750
7
8
9
10
11
12
13
$5,750
14
15
16
17
18
19
20
$5,750
21
22
23
24
25
26
27
$7,000
28
29
30
 $9,750
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,750
5
6
7
8
9
10
11
$9,750
12
13
14
15
16
17
18
$9,750
19
20
21
22
23
24
25
$9,750
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
$11,000
30
31
 $7,750
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,750
6
7
8
9
10
11
12
$7,000
13
14
15
16
17
18
19
$6,900
20
21
22
23
24
25
26
$6,800
27
28
29
30
 $6,700
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
Add Favorite
 
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BIALS

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Property Details
Chilmark, Charming Updated Menemsha Home. Water Views & Sunset Views, Quintessential Beach House.

On a hilltop overlooking the ocean in Menemsha sits this authentic Vineyard home. From one of the most desirable locations on the island, it's an easy walk to the...Read more

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

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Property Details
Katama Area Contemporary Cape, Newly Renovated 4 bedroom, Nicely Tucked on a Quiet Street, Private Deck & Spacious Yard Area

This lovely contemporary cape-style home tucked in the heart of Katama has undergone a complete gut renovation. Set on a large lot the home features a spacious back deck where families can dine...Read more

Location: 
Katama
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$6,500 - $11,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,500
7
8
9
10
11
12
13
$6,500
14
15
16
17
18
19
20
$6,500
21
22
23
24
25
26
27
$6,500
28
29
30
 $9,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,500
5
6
7
8
9
10
11
$9,500
12
13
14
15
16
17
18
$9,500
19
20
21
22
23
24
25
$9,500
26
27
28
29
30
31
 $9,500
August 2026
SuMoTuWeThFrSaWeek
 1
$9,500
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
$11,000
30
31
 $6,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,500
6
7
8
9
10
11
12
$6,500
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$6,500
27
28
29
30
 $6,500
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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MANUC

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Property Details
Hart Haven, Spacious Contemporary Colonial, Private Association Beach .8 mi from house, Private Association Tennis, 5 min walk from house

Located in the desirable enclave of homes known as Hart Haven just on the outskirts of Oak Bluffs Center, rental guests will surely enjoy this beautifully maintained home bordered by...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$10,000 - $11,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$10,000
7
8
9
10
11
12
13
$10,000
14
15
16
17
18
19
20
$10,000
21
22
23
24
25
26
27
$10,000
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
$10,000
19
20
21
22
23
24
25
$10,000
26
27
28
29
30
31
 $10,000
August 2026
SuMoTuWeThFrSaWeek
 1
$10,000
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
$11,000
30
31
 $10,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$10,000
6
7
8
9
10
11
12
$10,000
13
14
15
16
17
18
19
$10,000
20
21
22
23
24
25
26
$10,000
27
28
29
30
 $10,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
Add Favorite
 
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WEI33

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Property Details
Stunning, Charming, Historic Luxury Home in Edgartown Village Center, Newly Remodeled,

This beautifully remodeled historic home is nestled in the heart of Edgartown Village and boasts 4 bedrooms and 4.5 luxurious baths, complete with an array of inviting indoor and outdoor...Read more

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

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