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Spectacular Waterfront Views in exclusive Makonikey area, Ocean Views and Breathtaking Sunsets, Private Beach, Private Location

This serene waterfront retreat offers sweeping water views in an exceptionally private setting, yet is just a 10-minute drive from town, with access to fine dining, shopping, galleries, and entertainment....Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$12,000 - $12,000
June 2027
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July 2027
SuMoTuWeThFrSa
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August 2027
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$12,000
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$12,000
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$12,000
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September 2027
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Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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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:
$5,300 - $12,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
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8
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12
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$6,500
20
21
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23
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25
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$7,500
27
28
29
30
 $8,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$8,000
4
5
6
7
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9
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$8,500
11
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$9,000
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$10,000
25
26
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30
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$10,000
August 2027
SuMoTuWeThFrSaWeek
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$10,000
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$14,000
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$14,000
22
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27
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$12,000
29
30
31
 $8,500
September 2027
SuMoTuWeThFrSaWeek
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$8,500
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$6,300
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$5,300
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$5,300
26
27
28
29
30
 $5,300
Clean Fee: 
$650 per week
Tax: State & Local: 
14.45
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Outstanding In-town Home, Gorgeous Professionally Landscaped Yard, 5 Min walk to Main Street Shops & Restaurants

Located on a quiet street in the Edgartown Village area, this lovely 5 bedroom, 3 bath Home has been all newly updated. The home is bordered by lush lawn, privacy fencing...Read more

Location: 
Edgartown
Sleeps: 
9
Bedrooms: 
5
Baths: 
3
Price Range:
$7,000 - $12,000
June 2027
SuMoTuWeThFrSaWeek
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$7,000
6
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$8,000
13
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$8,000
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21
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25
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$9,000
27
28
29
30
 $10,000
July 2027
SuMoTuWeThFrSaWeek
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2
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$10,000
4
5
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$12,500
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$12,000
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19
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$12,000
25
26
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30
31
$12,000
August 2027
SuMoTuWeThFrSaWeek
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2
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$13,000
8
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$16,000
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$16,000
22
23
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27
28
$12,000
29
30
31
 $11,000
September 2027
SuMoTuWeThFrSaWeek
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$11,000
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$8,000
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$7,000
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$7,000
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29
30
 $7,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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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 2027
SuMoTuWeThFrSaWeek
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2
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$5,800
6
7
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10
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12
$5,800
13
14
15
16
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18
19
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21
22
23
24
25
26
$6,800
27
28
29
30
 $11,000
July 2027
SuMoTuWeThFrSaWeek
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2
3
$11,000
4
5
6
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$11,000
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$11,000
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19
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$12,000
25
26
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30
31
$12,000
August 2027
SuMoTuWeThFrSaWeek
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2
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$12,000
8
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$12,000
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$12,000
22
23
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25
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27
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$10,000
29
30
31
 $7,000
September 2027
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
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 $5,000
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

 

 

 

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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 - $12,000
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$6,000
6
7
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10
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12
$6,000
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$6,000
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26
$6,000
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28
29
30
 $12,000
July 2027
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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$12,000
August 2027
SuMoTuWeThFrSaWeek
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$14,500
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$14,500
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$14,500
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$12,500
29
30
31
 $11,500
September 2027
SuMoTuWeThFrSaWeek
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2
3
4
$11,500
5
6
7
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11
$7,500
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$6,000
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20
21
22
23
24
25
$6,000
26
27
28
29
30
 $6,000
Clean Fee: 
$750 per week
Tax: State & Local: 
14.45

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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Light Filled, Coastal Chic, all Newly Updated and Newly Furnished, Set in the Katama Area of Edgartown. Multiple Living Spaces!

Coastal Elegance 

Nestled in the heart of Katama, this beautiful home offers the perfect island retreat—less than a mile from South Beach. Walk or bike to the ocean, or launch...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$6,500 - $12,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
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12
13
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30
 $9,950
July 2027
SuMoTuWeThFrSaWeek
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2
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$9,950
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$9,950
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$9,950
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$9,950
25
26
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$9,950
August 2027
SuMoTuWeThFrSaWeek
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2
3
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5
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7
$12,000
8
9
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14
$12,000
15
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18
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20
21
$12,000
22
23
24
25
26
27
28
$9,950
29
30
31
 $7,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,500
5
6
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11
$6,500
12
13
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18
$6,500
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20
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22
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25
$6,500
26
27
28
29
30
 $6,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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Lovely, Newly Updated Oak Bluffs Home. Multiple Indoor/Outdoor Living/Lounge Areas, Sleeps 8, 10/15 minute Walk to the Vilage Center.

Note: All photos are virtually staged photos by the owner, all new furnishings will be arriving throughout the winter months. 

Welcome to Noble House, a beautifully updated home nestled in a charming neighborhood just...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
3
Baths: 
2
Price Range:
$5,310 - $11,560
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,250
6
7
8
9
10
11
12
$6,880
13
14
15
16
17
18
19
$7,500
20
21
22
23
24
25
26
$8,440
27
28
29
30
 $10,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$10,000
4
5
6
7
8
9
10
$10,000
11
12
13
14
15
16
17
$10,000
18
19
20
21
22
23
24
$10,620
25
26
27
28
29
30
31
$11,130
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$11,560
8
9
10
11
12
13
14
$11,560
15
16
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18
19
20
21
$11,560
22
23
24
25
26
27
28
$11,560
29
30
31
 $9,060
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,060
5
6
7
8
9
10
11
$8,750
12
13
14
15
16
17
18
$7,500
19
20
21
22
23
24
25
$7,190
26
27
28
29
30
 $6,880
Clean Fee: 
$400 per week
Tax: State & Local: 
14.45
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Lovely 3 bedroom water view home. Walk to town and Fuller St Beach,

This lovely 3 bedroom home features expansive water views, a beautifully landscaped yard, main living area with walls of glass windows providing beautiful views from within the home. Classic interior design with...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$6,000 - $11,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$9,000
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
$9,000
27
28
29
30
 $11,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$11,000
4
5
6
7
8
9
10
$11,000
11
12
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$11,000
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19
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23
24
$11,000
25
26
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30
31
$11,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$11,500
8
9
10
11
12
13
14
$11,500
15
16
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18
19
20
21
$11,500
22
23
24
25
26
27
28
$11,500
29
30
31
 $11,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,500
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
$9,000
26
27
28
29
30
 $9,000
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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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 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:
$8,000 - $11,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,000
6
7
8
9
10
11
12
$8,000
13
14
15
16
17
18
19
$8,000
20
21
22
23
24
25
26
$8,000
27
28
29
30
 $9,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,800
4
5
6
7
8
9
10
$9,800
11
12
13
14
15
16
17
$9,800
18
19
20
21
22
23
24
$9,800
25
26
27
28
29
30
31
$9,800
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,800
8
9
10
11
12
13
14
$10,500
15
16
17
18
19
20
21
$11,500
22
23
24
25
26
27
28
$9,800
29
30
31
 $9,800
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,800
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
$9,000
26
27
28
29
30
 $8,000
Clean Fee: 
$350 per week
Tax: State & Local: 
14.45
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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:
$7,500 - $11,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$9,500
6
7
8
9
10
11
12
$9,500
13
14
15
16
17
18
19
$9,500
20
21
22
23
24
25
26
$9,500
27
28
29
30
 $11,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$11,500
4
5
6
7
8
9
10
$11,500
11
12
13
14
15
16
17
$11,500
18
19
20
21
22
23
24
$11,500
25
26
27
28
29
30
31
$11,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$11,500
8
9
10
11
12
13
14
$11,500
15
16
17
18
19
20
21
$11,500
22
23
24
25
26
27
28
$11,500
29
30
31
 $10,000
September 2027
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
 $9,000
Clean Fee: 
$500
Tax: State & Local: 
11.7
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Stunning Luxury Home, Complete Renovation in Main House, Sweet Updated Guest House, Walk to Oak Bluffs Center

Gorgeous Luxury Home, Newly Renovated with Stylish Updates, Walking Distance to Oak Bluffs Center

This stunning bungalow-style home has undergone a complete renovation, blending luxury designer decor with the original...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,000 - $11,500
June 2027
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
$7,000
27
28
29
30
 $11,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$11,500
4
5
6
7
8
9
10
$11,500
11
12
13
14
15
16
17
$11,500
18
19
20
21
22
23
24
$11,500
25
26
27
28
29
30
31
$15,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$17,000
8
9
10
11
12
13
14
$17,000
15
16
17
18
19
20
21
$17,000
22
23
24
25
26
27
28
$15,000
29
30
31
 $7,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,000
5
6
7
8
9
10
11
$7,000
12
13
14
15
16
17
18
$7,000
19
20
21
22
23
24
25
$7,000
26
27
28
29
30
 
Clean Fee: 
$600 per week
Tax: State & Local: 
14.45
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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 2027
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
 $9,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,500
4
5
6
7
8
9
10
$9,500
11
12
13
14
15
16
17
$9,500
18
19
20
21
22
23
24
$9,500
25
26
27
28
29
30
31
$9,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$11,000
8
9
10
11
12
13
14
$11,000
15
16
17
18
19
20
21
$11,000
22
23
24
25
26
27
28
$11,000
29
30
31
 $11,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,000
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
 $6,500
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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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 2027
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
 $11,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$11,000
4
5
6
7
8
9
10
$11,000
11
12
13
14
15
16
17
$11,000
18
19
20
21
22
23
24
$11,000
25
26
27
28
29
30
31
$11,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$12,000
8
9
10
11
12
13
14
$12,000
15
16
17
18
19
20
21
$12,000
22
23
24
25
26
27
28
$12,000
29
30
31
 $11,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,000
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
 $10,000
Clean Fee: 
$600 per week
Tax: State & Local: 
14.45
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Superior New Luxury Build, Waterfront on the Lagoon, Multiple Indoor/Outdoor living Spaces. Private Association Beach Key, Deep Water Mooring

Nestled on Hines Point in Vineyard Haven, The Epitome of Summer Living offers sweeping vistas of the water from every room. With a sprawling screened porch, an upper-level deck, and...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$11,000 - $11,000
June 2027
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 2027
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
$20,000
25
26
27
28
29
30
31
$20,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$20,000
8
9
10
11
12
13
14
$22,500
15
16
17
18
19
20
21
$22,500
22
23
24
25
26
27
28
29
30
31
 
September 2027
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: 
$750 per week
Tax: State & Local: 
11.7

Owner provides a key to a beautiful private association Beach in Chilmark, Quansoo Beach, approximately a 25 minute drive from the house. Worth the drive!

 

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Historic 5 Bedroom Home, Newly Updated, Tucked in Historic Center of West Tisbury

Historic Charm in the Heart of Beautiful West Tisbury. This thoughtfully renovated home blends classic character with modern comfort, featuring a beautifully updated kitchen, three stylish baths, and five inviting...Read more

Location: 
West Tisbury
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$3,000 - $11,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,500
6
7
8
9
10
11
12
$4,500
13
14
15
16
17
18
19
$5,500
20
21
22
23
24
25
26
$5,500
27
28
29
30
 $7,750
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$7,750
4
5
6
7
8
9
10
$7,750
11
12
13
14
15
16
17
$7,750
18
19
20
21
22
23
24
$7,750
25
26
27
28
29
30
31
$7,750
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$11,000
8
9
10
11
12
13
14
$11,000
15
16
17
18
19
20
21
$11,000
22
23
24
25
26
27
28
$7,750
29
30
31
 $5,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,500
5
6
7
8
9
10
11
$3,500
12
13
14
15
16
17
18
$3,500
19
20
21
22
23
24
25
$3,500
26
27
28
29
30
 $3,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Owners are also open to weekday arrivals and departures to meet the need for auto ferry tickets. Please inquire to discuss! 

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