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Luxury Modern Farm House Design, Waterfront Pear Tree Cove on the Tisbury Great Pond, Rental Boat Access to South Shore Beach, Spectacular Area for Kayak Enthusiasts

New exquisite contemporary farmhouse design! Waterfront on the Tisbury Great Pond with access via boat rentals to gorgeous South Shore Beach. The beach area on the pond provides a great play space...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$7,500 - $13,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$8,500
7
8
9
10
11
12
13
$9,500
14
15
16
17
18
19
20
$9,500
21
22
23
24
25
26
27
$9,500
28
29
30
 $11,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,000
5
6
7
8
9
10
11
$11,000
12
13
14
15
16
17
18
$13,000
19
20
21
22
23
24
25
$13,000
26
27
28
29
30
31
 $13,500
August 2026
SuMoTuWeThFrSaWeek
 1
$13,500
2
3
4
5
6
7
8
$14,500
9
10
11
12
13
14
15
$14,500
16
17
18
19
20
21
22
$14,500
23
24
25
26
27
28
29
$14,500
30
31
 $9,500
September 2026
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
 $9,500
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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WEBSL

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Property Details
Menemsha

Magical Menemsha Cottage with water views of the Elizabeth Islands and harbor. The wooded property encompasses 3 private acres and is within walking distance to the village of Menemsha and...Read more

Location: 
Chilmark
Sleeps: 
7
Bedrooms: 
3
Baths: 
1
Price Range:
$4,350 - $8,520
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,050
7
8
9
10
11
12
13
$6,050
14
15
16
17
18
19
20
$6,050
21
22
23
24
25
26
27
$6,050
28
29
30
 $8,520
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,520
5
6
7
8
9
10
11
$8,520
12
13
14
15
16
17
18
$8,520
19
20
21
22
23
24
25
$8,520
26
27
28
29
30
31
 $8,520
August 2026
SuMoTuWeThFrSaWeek
 1
$8,520
2
3
4
5
6
7
8
$8,520
9
10
11
12
13
14
15
$8,520
16
17
18
19
20
21
22
$8,520
23
24
25
26
27
28
29
$8,520
30
31
 $6,310
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,310
6
7
8
9
10
11
12
$6,310
13
14
15
16
17
18
19
$6,310
20
21
22
23
24
25
26
$6,310
27
28
29
30
 $6,310
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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WEEKW

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CLASSIC, IN-TOWN EDGARTOWN, ENGLISH-COUNTRY CHIC LUXURY HOME WITH POOL AND MANICURED GROUNDS

Exquisite home in the village of Edgartown that exudes classic taste with English-Country styling.  This in-town location makes it easy to stroll down to dinner on the harbor or walk...Read more

Location: 
Edgartown
Sleeps: 
12
Bedrooms: 
7
Baths: 
6
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$12,500
7
8
9
10
11
12
13
$12,500
14
15
16
17
18
19
20
$15,000
21
22
23
24
25
26
27
$25,000
28
29
30
 $29,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$29,500
5
6
7
8
9
10
11
$29,500
12
13
14
15
16
17
18
$29,500
19
20
21
22
23
24
25
$29,500
26
27
28
29
30
31
 $29,500
August 2026
SuMoTuWeThFrSaWeek
 1
$29,500
2
3
4
5
6
7
8
$29,500
9
10
11
12
13
14
15
$29,500
16
17
18
19
20
21
22
$29,500
23
24
25
26
27
28
29
$29,500
30
31
 $12,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$12,500
6
7
8
9
10
11
12
$10,500
13
14
15
16
17
18
19
$10,500
20
21
22
23
24
25
26
$10,500
27
28
29
30
 $10,500
Clean Fee: 
$850 per week
Tax: State & Local: 
11.7
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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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WEI81

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Property Details
Lovely Oak Bluffs Escape, 3 Bedrooms in Main House, 2 Bedrooms over Garage, 3.5 Baths Multiple Living Spaces, Walk to Oak Bluffs Center, 1 Mile

Nestled on a tranquil cul-de-sac in the heart of Oak Bluffs, this meticulously renovated Modern Colonial offers a special Martha's Vineyard experience. Thoughtfully reimagined in 2025, the property encompasses a...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$70 - $10,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,000
7
8
9
10
11
12
13
$7,000
14
15
16
17
18
19
20
$7,000
21
22
23
24
25
26
27
$8,400
28
29
30
 $10,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$10,000
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
$10,000
26
27
28
29
30
31
 $10,000
August 2026
SuMoTuWeThFrSaWeek
 1
$10,000
2
3
4
5
6
7
8
$12,000
9
10
11
12
13
14
15
$14,000
16
17
18
19
20
21
22
$12,000
23
24
25
26
27
28
29
$10,000
30
31
 $10,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$10,000
6
7
8
9
10
11
12
$7,000
13
14
15
16
17
18
19
$7,000
20
21
22
23
24
25
26
$7,000
27
28
29
30
 $7,000
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
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WEINS

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Property Details
Charming and Pristine Hilltop Restored Farm House, Water views, Spectacular Sunsets, Set on Large Private Acreage

Hilltop House is located on one of the highest points on the Island displaying broad views across the rolling hills to beautiful water views beyond. Acres of undisturbed privacy and a...Read more

Location: 
Aquinnah
Sleeps: 
5
Bedrooms: 
3
Baths: 
2
Price Range:
$7,300 - $7,300
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
 $7,300
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,300
5
6
7
8
9
10
11
$7,300
12
13
14
15
16
17
18
$7,300
19
20
21
22
23
24
25
$7,300
26
27
28
29
30
31
 $7,300
August 2026
SuMoTuWeThFrSaWeek
 1
$7,300
2
3
4
5
6
7
8
$7,300
9
10
11
12
13
14
15
$7,300
16
17
18
19
20
21
22
$7,300
23
24
25
26
27
28
29
30
31
 $6,800
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,800
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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WEISM

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Property Details
Outstanding Tri -Level Katama Home, Pool, new 18 x 40 Heated Saltwater Pool, Bluestone Patio, Fire Pit, Walk or Bike to South Beach and 5 minute Drive to Edgartown Village Area

Beautiful tri-level contemporary home with an 18 x 40 heated saltwater pool, bluestone patio, outdoor dining area, chaise lounge chairs, and fire pit. This recently updated home includes a spacious open floor plan with vaulted ceilings, a...Read more

Location: 
Katama
Sleeps: 
10
Bedrooms: 
4
Baths: 
4
Price Range:
$7,500 - $17,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$8,500
7
8
9
10
11
12
13
$9,000
14
15
16
17
18
19
20
$10,500
21
22
23
24
25
26
27
$12,500
28
29
30
 $14,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$14,000
5
6
7
8
9
10
11
$17,500
12
13
14
15
16
17
18
$17,500
19
20
21
22
23
24
25
$17,500
26
27
28
29
30
31
 $18,000
August 2026
SuMoTuWeThFrSaWeek
 1
$18,000
2
3
4
5
6
7
8
$18,000
9
10
11
12
13
14
15
$18,000
16
17
18
19
20
21
22
$18,000
23
24
25
26
27
28
29
$14,000
30
31
 $10,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$10,500
6
7
8
9
10
11
12
$9,200
13
14
15
16
17
18
19
$7,500
20
21
22
23
24
25
26
$7,500
27
28
29
30
 $7,500
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

Ferry Tickets available 6/27-7/4, 7/4-7/11, 8/22-8/29, 8/29-9/5 - please inquire

 

Pool is heated to 84 degrees July & August &  included in the rental rate.

 

Pool heated to 84 degrees June & September, additional $500/week propane surcharge.

 

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WESTC

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Property Details
Summer Wind in the Heart of Oak Bluffs, Water views. 2 minute Walk to Inkwell Beach & 5 minute walk to town, All Newly Remodeled 5 Bedroom, 3 Bath Home With Deluxe Amenities

Set in the heart of Oak Bluffs center, this newly renovated home features water views, walk to Inkwell Beach and Pay Beach and walk to the town center all within...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$8,000 - $8,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$8,000
7
8
9
10
11
12
13
14
15
16
17
18
19
20
$9,000
21
22
23
24
25
26
27
$10,000
28
29
30
 $12,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$12,000
5
6
7
8
9
10
11
$12,000
12
13
14
15
16
17
18
$13,000
19
20
21
22
23
24
25
$14,000
26
27
28
29
30
31
 $14,000
August 2026
SuMoTuWeThFrSaWeek
 1
$14,000
2
3
4
5
6
7
8
$19,000
9
10
11
12
13
14
15
$19,000
16
17
18
19
20
21
22
$19,000
23
24
25
26
27
28
29
$12,000
30
31
 $9,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$9,000
6
7
8
9
10
11
12
$7,000
13
14
15
16
17
18
19
$7,000
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$550
Tax: State & Local: 
11.7

Ferry tickets available for purchase, 7/26 - 8/2  Please inquire   (mv)

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WESTD

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Property Details
Deep Bottom Custom Contemporary, Heated Pool, Association Tennis Courts, Features Multiple Living Spaces on 3 Levels, A/C WiFi

Custom crafted contemporary home set on lush professionally landscaped grounds. The pool and patio area overlook the large yard with expansive views of the common meadows. There are private association...Read more

Location: 
West Tisbury
Sleeps: 
9
Bedrooms: 
6
Baths: 
4
Price Range:
$8,500 - $12,100
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
$11,000
28
29
30
 $12,100
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$12,100
5
6
7
8
9
10
11
$12,100
12
13
14
15
16
17
18
$12,100
19
20
21
22
23
24
25
$12,100
26
27
28
29
30
31
 $12,500
August 2026
SuMoTuWeThFrSaWeek
 1
$12,500
2
3
4
5
6
7
8
$12,500
9
10
11
12
13
14
15
$12,500
16
17
18
19
20
21
22
$12,500
23
24
25
26
27
28
29
$11,500
30
31
 $9,000
September 2026
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
 $9,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Pool heated to 81 July & August included in rental rate.

Pool heated to 81 June & September additional $275 per week 

Pool is 18 x 38 with a deep end, no diving board

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

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