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Meadow View Farms, Out of Town, Association Tennis, Hi Speed Internet
Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,900 - $3,000
June 2026
SuMoTuWeThFrSaWeek
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7
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12
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24
25
26
27
$2,900
28
29
30
 $3,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,000
5
6
7
8
9
10
11
$3,000
12
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15
16
17
18
$3,000
19
20
21
22
23
24
25
$3,000
26
27
28
29
30
31
 $3,000
August 2026
SuMoTuWeThFrSaWeek
 1
$3,000
2
3
4
5
6
7
8
$3,000
9
10
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15
$3,000
16
17
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20
21
22
$3,000
23
24
25
26
27
28
29
$3,000
30
31
 $2,900
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,900
6
7
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10
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12
$2,900
13
14
15
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17
18
19
$2,900
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$360 per week
Tax: State & Local: 
11.7
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Exclusive Makonikey Location, Custom Home with Designer Details, Private Association Beach

Hilltop Cottage, beautiful and custom-crafted with attention to details guests will appreciate. A completed gut renovation that includes AC throughout, two bedrooms and two baths, an open main living area with...Read more

Location: 
West Tisbury
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,750 - $3,000
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
$3,500
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
$4,000
19
20
21
22
23
24
25
$4,500
26
27
28
29
30
31
 $4,500
August 2026
SuMoTuWeThFrSaWeek
 1
$4,500
2
3
4
5
6
7
8
$4,500
9
10
11
12
13
14
15
$4,500
16
17
18
19
20
21
22
$4,500
23
24
25
26
27
28
29
$4,000
30
31
 $3,250
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,250
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
$3,000
27
28
29
30
 $2,750
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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Lovely Cape, 7 minute walk to town and harbor area, 4 bedrooms, 3 baths, sleeps 7

Lovely 4 bedroom, 3 bath home, pristinely maintained and ideally located just on the outskirts of Oak Bluffs on a quiet street. Short walk to town center and Oak Bluffs town...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
3
Price Range:
$3,000 - $3,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
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7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
$3,800
28
29
30
 $4,600
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,600
5
6
7
8
9
10
11
$4,600
12
13
14
15
16
17
18
$4,600
19
20
21
22
23
24
25
$4,600
26
27
28
29
30
31
 $5,250
August 2026
SuMoTuWeThFrSaWeek
 1
$5,250
2
3
4
5
6
7
8
$5,300
9
10
11
12
13
14
15
$5,500
16
17
18
19
20
21
22
$5,300
23
24
25
26
27
28
29
$4,300
30
31
 $3,200
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,200
6
7
8
9
10
11
12
$3,200
13
14
15
16
17
18
19
$3,000
20
21
22
23
24
25
26
$3,000
27
28
29
30
 $3,000
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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Cozy, newly updated Vineyard Haven Cottage, 2 Bedrooms, 1 Bath, Sleeps 4. Spacious Deck with Dining Area & Grill

Nestled on the outskirts of Vineyard Haven, this charming cottage is ideal for small families or two couples seeking a serene retreat. Just a leisurely 15-minute stroll from Main St,...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$2,000 - $3,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
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7
8
9
10
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12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
$3,000
28
29
30
 $3,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,500
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
31
 $3,500
August 2026
SuMoTuWeThFrSaWeek
 1
$3,500
2
3
4
5
6
7
8
$3,500
9
10
11
12
13
14
15
$3,500
16
17
18
19
20
21
22
$3,500
23
24
25
26
27
28
29
$3,500
30
31
 $3,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,000
6
7
8
9
10
11
12
$2,500
13
14
15
16
17
18
19
$2,500
20
21
22
23
24
25
26
$2,500
27
28
29
30
 $2,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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Cozy Sunny 3 Bedroom Contemporary, Spacious Deck, Situated in a Quiet Neighborhood just on the outskirts of Vineyard Haven Village Center

Located on a quiet residential circle in Vineyard Haven, this pristine sweet home with oversized windows is contemporary, yet rustic with exposed wooden beams and a cathedral ceiling.  New natural travertine...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
3
Baths: 
2
Price Range:
$2,750 - $2,750
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
$2,400
28
29
30
 $2,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$2,500
5
6
7
8
9
10
11
$2,500
12
13
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18
$2,500
19
20
21
22
23
24
25
$2,500
26
27
28
29
30
31
 $2,500
August 2026
SuMoTuWeThFrSaWeek
 1
$2,500
2
3
4
5
6
7
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12
13
14
15
16
17
18
19
20
21
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28
29
30
31
 
September 2026
SuMoTuWeThFrSa
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2
3
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12
13
14
15
16
17
18
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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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Hidden Cove, Centrally Located to Beaches and Towns, Association Tennis Courts, A/C, WiFi

Centrally located in the Hidden Cove community of homes on the outskirts of Oak Bluffs. Lovely area to bike, walk, or play tennis at the association courts. 

The main level features an...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,600 - $2,600
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
$3,200
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
$4,200
19
20
21
22
23
24
25
$4,200
26
27
28
29
30
31
 $4,500
August 2026
SuMoTuWeThFrSaWeek
 1
$4,500
2
3
4
5
6
7
8
$4,500
9
10
11
12
13
14
15
$4,500
16
17
18
19
20
21
22
$4,500
23
24
25
26
27
28
29
$3,400
30
31
 $2,600
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,600
6
7
8
9
10
11
12
$2,600
13
14
15
16
17
18
19
$2,600
20
21
22
23
24
25
26
$2,600
27
28
29
30
 $2,600
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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Cozy Contemporary Home with Designer Interior Details , Centrally Located to Towns and Beaches

WELCOME TO SANDPIPER COTTAGE, YOUR STYLISH FAMILY RETREAT!

Four bedrooms include a primary bedroom with a queen bed on the 1st level with a television and a full bath across the...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$1,600 - $2,600
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
 $3,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,500
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
31
 
August 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
$3,200
30
31
 $2,800
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,800
6
7
8
9
10
11
12
$2,600
13
14
15
16
17
18
19
$2,600
20
21
22
23
24
25
26
$1,600
27
28
29
30
 $1,600
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
Add Favorite
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Sengekontacket - Waterfront Cottage, Panoramic Views and Amazing Sunrises

Charming Vintage Summer Cottage on Sengekontacket Pond

Experience the beauty of this vintage cottage perched on the shores of Sengekontacket Pond, offering stunning water views across the pond to North...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
4
Baths: 
2
Price Range:
$2,500 - $2,500
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
$1,900
28
29
30
 $3,900
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,900
5
6
7
8
9
10
11
$3,900
12
13
14
15
16
17
18
$3,900
19
20
21
22
23
24
25
$3,900
26
27
28
29
30
31
 $3,900
August 2026
SuMoTuWeThFrSaWeek
 1
$3,900
2
3
4
5
6
7
8
$3,900
9
10
11
12
13
14
15
$3,900
16
17
18
19
20
21
22
$3,900
23
24
25
26
27
28
29
$3,900
30
31
 $2,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,500
6
7
8
9
10
11
12
$2,500
13
14
15
16
17
18
19
$2,500
20
21
22
23
24
25
26
$2,500
27
28
29
30
 $2,500
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
Add Favorite
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Cottage with Screened Porch, Close to Menemsha Village Area and just a Short Drive to Lucy Vincent Beacn

Menemsha Crossroads sweet cottage in a private wooded area, perfect for a family of four. Features 2 bedrooms, a primary with bath, and the 2nd bedroom uses a hall bath. The...Read more

Location: 
Chilmark
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,500 - $2,500
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
$2,500
28
29
30
 $3,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,000
5
6
7
8
9
10
11
$3,000
12
13
14
15
16
17
18
$3,000
19
20
21
22
23
24
25
$3,000
26
27
28
29
30
31
 $3,000
August 2026
SuMoTuWeThFrSaWeek
 1
$3,000
2
3
4
5
6
7
8
$3,500
9
10
11
12
13
14
15
$3,500
16
17
18
19
20
21
22
$3,500
23
24
25
26
27
28
29
$3,500
30
31
 $2,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,500
6
7
8
9
10
11
12
$2,500
13
14
15
16
17
18
19
$2,500
20
21
22
23
24
25
26
$2,500
27
28
29
30
 $2,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
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Central Location with Ease of Access to Village Centers and Multiple Beaches

Lovely vacation home budget-friendly in a quiet residential area and centrally located with a short drive to town centers of Oak Bluffs, Edgartown, and Vineyard Haven. Multiple Beaches 10 to 15-minute drive...Read more

Location: 
Edgartown
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,200 - $2,500
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
28
29
30
 $2,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$2,700
5
6
7
8
9
10
11
$2,900
12
13
14
15
16
17
18
$2,900
19
20
21
22
23
24
25
$2,900
26
27
28
29
30
31
 $2,900
August 2026
SuMoTuWeThFrSaWeek
 1
$2,900
2
3
4
5
6
7
8
$3,000
9
10
11
12
13
14
15
$3,000
16
17
18
19
20
21
22
$3,000
23
24
25
26
27
28
29
$3,000
30
31
 $2,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,500
6
7
8
9
10
11
12
$2,500
13
14
15
16
17
18
19
$2,400
20
21
22
23
24
25
26
$2,400
27
28
29
30
 $2,200
Clean Fee: 
Included
Tax: State & Local: 
11.7
Add Favorite
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Adorable Updated 2 Bedroom 1.5 Bath Cottage, Walk to Town, Harbor and Beach

If you are looking for an adorable cottage-style home in the center of Oak Bluffs this newly updated, tastefully decorated 2 bedroom, with one full bath and a half bath, is sure to...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
1
Price Range:
$2,500 - $2,500
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
$2,700
28
29
30
 $3,800
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,800
5
6
7
8
9
10
11
$3,800
12
13
14
15
16
17
18
$3,800
19
20
21
22
23
24
25
$3,800
26
27
28
29
30
31
 $3,800
August 2026
SuMoTuWeThFrSaWeek
 1
$3,800
2
3
4
5
6
7
8
$4,500
9
10
11
12
13
14
15
$4,500
16
17
18
19
20
21
22
$4,500
23
24
25
26
27
28
29
$3,500
30
31
 $3,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,000
6
7
8
9
10
11
12
$2,500
13
14
15
16
17
18
19
$2,500
20
21
22
23
24
25
26
$2,500
27
28
29
30
 $2,500
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
Add Favorite
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Mink Meadow Guest Cottage, Overlooks Golf Course, Walk to Beach 5 min walk from House, Mink Meadows Golf Course, 1 mile to Clubhouse

Cozy guest cottage with designer touches throughout. As the guest cottage to the main house, this adorable cottage is private from the main house and has its own drive and...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$1,900 - $2,100
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
$1,900
28
29
30
 $2,100
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$2,100
5
6
7
8
9
10
11
$2,100
12
13
14
15
16
17
18
$2,100
19
20
21
22
23
24
25
$2,100
26
27
28
29
30
31
 $2,100
August 2026
SuMoTuWeThFrSaWeek
 1
$2,100
2
3
4
5
6
7
8
$2,100
9
10
11
12
13
14
15
$2,100
16
17
18
19
20
21
22
$2,100
23
24
25
26
27
28
29
$2,100
30
31
 $1,900
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$1,900
6
7
8
9
10
11
12
$1,900
13
14
15
16
17
18
19
$1,900
20
21
22
23
24
25
26
$1,900
27
28
29
30
 $1,900
Clean Fee: 
$150 per week
Tax: State & Local: 
11.7
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Seaview Condo Unit, Gorgeous Water Views, In Town Location, Modern updated Interior!

Note: Seaview Condos is a 3-minute walk from the Steamship Authority dock in Oak Bluffs and two blocks from the Island Queen ferry dock. Perfect location if you cannot or do...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,100 - $2,100
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
$3,500
28
29
30
 $3,800
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,800
5
6
7
8
9
10
11
$3,900
12
13
14
15
16
17
18
$4,600
19
20
21
22
23
24
25
$4,600
26
27
28
29
30
31
 $5,600
August 2026
SuMoTuWeThFrSaWeek
 1
$5,600
2
3
4
5
6
7
8
$5,600
9
10
11
12
13
14
15
$5,600
16
17
18
19
20
21
22
$5,600
23
24
25
26
27
28
29
$3,900
30
31
 $2,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,500
6
7
8
9
10
11
12
$2,500
13
14
15
16
17
18
19
$2,100
20
21
22
23
24
25
26
$2,100
27
28
29
30
 $2,100
Clean Fee: 
$240 per week
Tax: State & Local: 
11.7

5 minute walk from Steamship Authority Oak Bluffs dock to the Seaview Condos.  2 blocks from the Island Queen ferry dock.  

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Waterfront, Private Beach, Gorgeous Water Views, Room AC, Wifi

MVVR EXCLUSIVE:  Classic, beach cottage with spectacular views across the sound, calm water swimming, and a great area for kayaking. The open kitchen, dining, and living areas are enhanced by the wall of windows...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
3
Baths: 
1
Price Range:
$1,900 - $1,900
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
$2,900
28
29
30
 $3,200
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,200
5
6
7
8
9
10
11
$3,200
12
13
14
15
16
17
18
$3,200
19
20
21
22
23
24
25
$3,200
26
27
28
29
30
31
 $3,300
August 2026
SuMoTuWeThFrSaWeek
 1
$3,300
2
3
4
5
6
7
8
$3,300
9
10
11
12
13
14
15
$3,300
16
17
18
19
20
21
22
$3,300
23
24
25
26
27
28
29
$2,900
30
31
 $2,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,000
6
7
8
9
10
11
12
$2,000
13
14
15
16
17
18
19
$2,000
20
21
22
23
24
25
26
$2,000
27
28
29
30
 $1,900
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7

Cottage books Tuesday to Tuesday July & August weeks

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Pristine Bungalow, Peekaboo Water View of Lagoon, Private Path to the Lagoon Waterfront from the Yard, 2 Kayaks Provided

THOREAU'S SPIRIT LIVES - An original 1920's summer bungalow lovingly restored to perfection. Two plus acres of quiet comfort, surrounded by farmland and woods. Walk down the long lawn past...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
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
$3,050
28
29
30
 $3,050
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,050
5
6
7
8
9
10
11
$3,050
12
13
14
15
16
17
18
$3,050
19
20
21
22
23
24
25
$3,300
26
27
28
29
30
31
 $3,300
August 2026
SuMoTuWeThFrSaWeek
 1
$3,300
2
3
4
5
6
7
8
$3,600
9
10
11
12
13
14
15
$3,600
16
17
18
19
20
21
22
$3,600
23
24
25
26
27
28
29
$3,300
30
31
 $2,100
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,100
6
7
8
9
10
11
12
$2,100
13
14
15
16
17
18
19
$2,100
20
21
22
23
24
25
26
$2,100
27
28
29
30
 
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7

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