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East Chop Waterfront, Extraordinary Sunsets &Views Across the Sound , Deck directly on the Beach, Casual Interior

Classic, casual beachfront home combines cottage styling with modern amenities. spectacular views, quietly lapping waves right outside your windows, and breathtaking sunsets. Ideally located in the East Chop Area of Oak Bluffs just a short distance...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$6,000 - $13,800
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,900
7
8
9
10
11
12
13
$6,900
14
15
16
17
18
19
20
$8,000
21
22
23
24
25
26
27
$8,000
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
$9,700
19
20
21
22
23
24
25
$9,700
26
27
28
29
30
31
 $9,700
August 2026
SuMoTuWeThFrSaWeek
 1
$9,700
2
3
4
5
6
7
8
$13,800
9
10
11
12
13
14
15
$13,800
16
17
18
19
20
21
22
$13,800
23
24
25
26
27
28
29
$11,200
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
$7,000
20
21
22
23
24
25
26
$6,000
27
28
29
30
 $6,000
Clean Fee: 
$480 per week
Tax: State & Local: 
11.7

 

 

 

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MILTD

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Property Details
Perfect in Town Location. Just 1 to 2 blocks to Beach, Town Center & Harbor Area, Walk to and from the Ferry

Centrally located in the heart of Oak Bluffs, walk 1-2 blocks to the beach, public tennis courts, and town & harbor areas. This wonderful large home has a large wrap-around porch for relaxing, 7...Read more

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

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Property Details
Mini Retreat with Pool, Private Peaceful Chilmark Location, Lucy Vincent and Menemsha Beaches Nearby.

Impeccably maintained and updated, this adorable summer home is perfect for families looking for luxury features such as quality linens in a quiet location. The 12 by 18-foot spa pool is...Read more

Location: 
Chilmark
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,800 - $13,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,350
7
8
9
10
11
12
13
$7,350
14
15
16
17
18
19
20
$8,000
21
22
23
24
25
26
27
$12,400
28
29
30
 $13,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$13,000
5
6
7
8
9
10
11
$13,000
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
$13,500
9
10
11
12
13
14
15
$13,500
16
17
18
19
20
21
22
$13,500
23
24
25
26
27
28
29
$13,000
30
31
 $8,300
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,300
6
7
8
9
10
11
12
$7,650
13
14
15
16
17
18
19
$7,650
20
21
22
23
24
25
26
$7,650
27
28
29
30
 $4,800
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

Pool heated to 82 degrees included in rental rate July & August

Pool heated to 82 degrees, May, June Sept and October additional $150 per week propane surcharge

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HOSTH

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Property Details
Gorgeous Custom Contemporary Farmhouse Design, Heated Pool & Spa, Located Just on the Outskirts of Edgartown Center! 4 Bedrooms, 4.5 Baths

Heated Pool and Outdoor Living

Enjoy a beautifully designed 30x16' heated pool with a depth ranging from 3.7 feet at the shallow end to 7 feet at the deep end....Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$3,430 - $13,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,500
7
8
9
10
11
12
13
$7,500
14
15
16
17
18
19
20
$7,500
21
22
23
24
25
26
27
$10,500
28
29
30
 $12,750
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$12,750
5
6
7
8
9
10
11
$12,750
12
13
14
15
16
17
18
$12,750
19
20
21
22
23
24
25
$12,750
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
$13,500
30
31
 $10,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$10,500
6
7
8
9
10
11
12
$7,500
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: 
$575
Tax: State & Local: 
11.7

Pool heated to 80 included in the rental rate last week in June through the last week in August. Spa is heated to the same temperature as pool. 

Per a renter request the spa can be heated to 101, 4 hours per day 6 to 10 pm for an additional $200 per week.

 

June & September weeks pool heated to 80 additional $250 propane surcharge week, request for higher temperatures, speak with an agent. Spa is heated to the same temperature as the Pool.  Requests for Spa heated to 101 4 hours per day additional $200 per week. 

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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:
$6,000 - $13,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$8,000
7
8
9
10
11
12
13
$8,000
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
 $17,000
August 2026
SuMoTuWeThFrSaWeek
 1
$17,000
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
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BAKE7

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Property Details
Waterview, Walk to the Beach and Town Center, Impeccably Maintained 4 bedroom Home set in the Heart of Oak Bluffs.
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,400 - $13,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,400
7
8
9
10
11
12
13
$4,400
14
15
16
17
18
19
20
$4,900
21
22
23
24
25
26
27
$4,900
28
29
30
 $9,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,000
5
6
7
8
9
10
11
$11,000
12
13
14
15
16
17
18
$11,000
19
20
21
22
23
24
25
$11,000
26
27
28
29
30
31
 $12,000
August 2026
SuMoTuWeThFrSaWeek
 1
$12,000
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
$13,000
23
24
25
26
27
28
29
$13,000
30
31
 $11,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$11,000
6
7
8
9
10
11
12
$6,000
13
14
15
16
17
18
19
$5,700
20
21
22
23
24
25
26
$5,700
27
28
29
30
 $5,700
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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ROBDE

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Property Details
Edgartown, Katama Area, Spacious Luxury with Designer Detailing, Chef's Kitchen, Multiple Living Spaces, 4 Bedrooms, 3.5 Baths

New in 2022 large addition and full renovation to this beautiful Katama home. Located within walking distance of town (1.4 miles) and biking to Katama South Beach (2.1 miles). 

The...Read more

Location: 
Katama
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$13,000 - $13,000
June 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
 
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
 $15,000
August 2026
SuMoTuWeThFrSaWeek
 1
$15,000
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
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: 
$550 per week
Tax: State & Local: 
11.7

Sales Tax Exempt for weeks 8/8 & 8/15

 

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SHAN2

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Property Details
Newly Updated Vacation Home, Katama Area of Edgartown, 12 x 30' Heated Pool, 4 Bedrooms, 4.5 Baths, Separate Recreation Barn with Ping Pong Table, Large Screen TV and Game Area, Bike Path to Village Center and to South Beach

Outstanding, modern farmhouse design, with heated pool and additional entertainment barn with ping-pong table, game table, game board games, and large screened TV just a few steps across the yard....Read more

Location: 
Katama
Sleeps: 
12
Bedrooms: 
4
Baths: 
4
Price Range:
$7,350 - $12,650
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,350
7
8
9
10
11
12
13
$8,920
14
15
16
17
18
19
20
$11,020
21
22
23
24
25
26
27
$12,650
28
29
30
 $13,650
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$13,650
5
6
7
8
9
10
11
$13,650
12
13
14
15
16
17
18
$13,650
19
20
21
22
23
24
25
$14,700
26
27
28
29
30
31
 $15,220
August 2026
SuMoTuWeThFrSaWeek
 1
$15,220
2
3
4
5
6
7
8
$15,220
9
10
11
12
13
14
15
$15,220
16
17
18
19
20
21
22
$15,220
23
24
25
26
27
28
29
$10,500
30
31
 $8,920
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,920
6
7
8
9
10
11
12
$7,580
13
14
15
16
17
18
19
$7,350
20
21
22
23
24
25
26
$7,350
27
28
29
30
 $7,350
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Pool Heated to 80 degrees July & August included in rental rates. 

Pool heat is an additional $250 May, June, September, October

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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 - $12,500
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 

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ROGLM

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Property Details
Coastal Contemporary Beach House, Newly updated! Located under a mile from South Beach & 2 miles from Edgartown Center.

Feel the south shore breezes at this great vacation home ideally located in the Katama area. The proximity to both South Beach and Edgartown village center makes this home an ideal choice...Read more

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

(0)Inquire/Share
Property Details
Exquisite New Contemporary Waterfront Home, Multiple Indoor& Outdoor Living Spaces with Waterviews.

This stunning luxury waterfront home, nestled on the Lagoon, offers breathtaking water views from every corner of the newly built residence. Enjoy the seamless transition between indoor and outdoor living...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
3
Baths: 
4
Price Range:
$10,000 - $12,500
June 2026
SuMoTuWeThFrSa
 1
2
3
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July 2026
SuMoTuWeThFrSa
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August 2026
SuMoTuWeThFrSa
 1
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September 2026
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Owner requires two week minimum booking during months July & August

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HUESC

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Property Details
Lovely 6 Bedroom Home in Heart of Katama, Multiple Living Spaces, Perfect for Extended Families, 8/10ths mile to South Beach

Ideally situated in the heart of the Katama area of Edgartown. and just 8/10 of a mile from South Beach, this beautifully expanded Cape-style home is perfectly designed for extended families...Read more

Location: 
Katama
Sleeps: 
11
Bedrooms: 
6
Baths: 
3
Price Range:
$4,150 - $12,000
June 2026
SuMoTuWeThFrSaWeek
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$4,450
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$4,450
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$4,450
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$6,000
28
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 $10,000
July 2026
SuMoTuWeThFrSaWeek
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$10,000
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$10,000
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$10,000
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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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$12,000
30
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 $7,850
September 2026
SuMoTuWeThFrSaWeek
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$7,850
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$6,500
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$6,500
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$6,500
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 $6,500
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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CLARA

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Property Details
Exclusive Makonikey Area Home, Private Landscaped Yard, Large Deck Area, 4 bedrooms & 4 Baths. Short Drive to Towns and Multiple Beaches

Family and friends are sure to enjoy this pristinely maintained and spacious home situated in a private and quiet location. Beautiful yard and deck area with outdoor seating and a patio dining area that...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$4,000 - $12,000
June 2026
SuMoTuWeThFrSaWeek
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 $5,000
July 2026
SuMoTuWeThFrSaWeek
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2
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$5,000
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$5,000
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$5,500
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$6,000
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 $6,000
August 2026
SuMoTuWeThFrSaWeek
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$6,000
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$12,000
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$12,000
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$12,000
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$6,500
30
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 $5,500
September 2026
SuMoTuWeThFrSaWeek
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$5,500
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$5,500
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$4,000
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$4,000
27
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 $4,000
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

Sheets & Towels are not provided. Rental guests need to bring sheets & towels or they can be rented and delivered per the instructions from the linen rental company. www.marthaslinenrental.com

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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 - $12,000
June 2026
SuMoTuWeThFrSaWeek
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$6,500
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$6,500
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$6,500
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$7,500
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 $8,000
July 2026
SuMoTuWeThFrSaWeek
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$8,000
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$9,000
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$9,000
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$10,000
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 $10,000
August 2026
SuMoTuWeThFrSaWeek
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$10,000
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$12,000
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$12,000
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$12,000
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$8,500
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31
 $6,500
September 2026
SuMoTuWeThFrSaWeek
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$6,500
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$5,500
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$5,500
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$5,000
27
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 $5,000
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
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SIMOA

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Property Details
Exquisite New Luxury Home, Saltwater Pool 18 x 32 and Hot Tub, Ideally Situated in the Village Area, Walk to Shops, Dining and Harbor Area

Welcome to this gorgeous, and all newly renovated Edgartown Village area luxury home.  This spacious home features an expansive outside entertainment area with a heated saltwater pool, hot tub, large patio surround, and deck with...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$12,000 - $12,000
June 2026
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July 2026
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August 2026
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September 2026
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Clean Fee: 
$600
Tax: State & Local: 
11.7

Pool Heated to 82 degrees July & August weeks included in the rental rate, June & September weeks additional $300 per week ( begins 9/6 for 2025)

 

 

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