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Modern, Newly Renovated, Architecturally Significant Beach Cottage Design. Close to Town and Beaches, Tucked in the Lovely Community of Summer Homes, Waterview Farms!

Gorgeous all newly renovated and newly furnished mid-century beach cottage, now a modern vacation oasis designed by the prominent interior design firm, - Tersigni Palachek. This eloquent, yet beachy home offers...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,600 - $4,100
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,500
8
9
10
11
12
13
14
$3,500
15
16
17
18
19
20
21
$3,900
22
23
24
25
26
27
28
$3,900
29
30
 $6,500
July 2025
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
31
 $6,400
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,400
3
4
5
6
7
8
9
$6,600
10
11
12
13
14
15
16
$6,600
17
18
19
20
21
22
23
$6,600
24
25
26
27
28
29
30
$6,600
31
 $6,600
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,600
7
8
9
10
11
12
13
$4,100
14
15
16
17
18
19
20
$4,100
21
22
23
24
25
26
27
$4,100
28
29
30
 $2,600
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

Rate reduced for week 7/11-7/18 - see calendar for adjusted rates

 

Owner books Fri to Fri July & August weeks!

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Waterfront, Water View, Walk to Beach

Casual immaculately clean in picturesque Menemsha, Chilmark waterfront. Beautiful views. A short stroll to the beach, fish market, boutiques, fishing, and shore dinners. Guest House - Main House on property...Read more

Location: 
Chilmark
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,000 - $4,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,700
8
9
10
11
12
13
14
$3,700
15
16
17
18
19
20
21
$3,700
22
23
24
25
26
27
28
$3,700
29
30
 $4,700
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,700
6
7
8
9
10
11
12
$4,700
13
14
15
16
17
18
19
$4,700
20
21
22
23
24
25
26
$4,700
27
28
29
30
31
 $4,700
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,700
3
4
5
6
7
8
9
$4,700
10
11
12
13
14
15
16
$4,700
17
18
19
20
21
22
23
$4,700
24
25
26
27
28
29
30
$4,700
31
 $3,700
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,700
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
 $4,000
Clean Fee: 
$300 per week, owner will provide sheets, towels, beach towels, additional $225 per rental period
Tax: State & Local: 
11.7

Owner will provide, sheets, towels & beach towels for an additional $225 per rented period. 

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North Slope Hilltop House. Private yard, Screeened Porch and Patio, 8 minute drive to Lucy Vincent Beach or Menemsha Village

Delightful, 3 bedroom, 2 bath home with AC. Private Chilmark hilltop location! This sweet home features an open kitchen, living, and dining area, and a screened porch for your summer...Read more

Location: 
Chilmark
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,600 - $4,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
$3,600
15
16
17
18
19
20
21
$3,600
22
23
24
25
26
27
28
$3,800
29
30
 $3,800
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,800
6
7
8
9
10
11
12
$3,800
13
14
15
16
17
18
19
$3,800
20
21
22
23
24
25
26
$3,800
27
28
29
30
31
 $4,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,000
3
4
5
6
7
8
9
$4,000
10
11
12
13
14
15
16
$4,000
17
18
19
20
21
22
23
$4,000
24
25
26
27
28
29
30
$4,000
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$3,800
14
15
16
17
18
19
20
$3,800
21
22
23
24
25
26
27
$3,600
28
29
30
 $3,600
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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Stylish and Beautifully Decorated Summer Residence, Screened Porch, Spacious Deck, WiFi

Centrally located mid-island, this beautifully appointed home features an open design kitchen, dining, and living areas for easy entertaining with family and friends.  French doors off of the living area...Read more

Location: 
Edgartown
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,100 - $4,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,350
8
9
10
11
12
13
14
$2,350
15
16
17
18
19
20
21
$2,350
22
23
24
25
26
27
28
$3,700
29
30
 $4,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
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
31
 $4,300
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,300
3
4
5
6
7
8
9
$4,300
10
11
12
13
14
15
16
$4,300
17
18
19
20
21
22
23
$4,300
24
25
26
27
28
29
30
$4,300
31
 $2,350
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,350
7
8
9
10
11
12
13
$2,350
14
15
16
17
18
19
20
$2,350
21
22
23
24
25
26
27
$2,350
28
29
30
 $2,100
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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Charming Katama Cape Style Home, Screened Porch with Dining, Deck and Farmers Porch, 3 minute drive to South Beach and 5 minute drive to Edgartown Village

A charming Katama home, set equidistance, 1.5 miles, between South Beach and Edgartown Village Center. 

Multiple outdoor areas include a farmer's porch with rockers, a spacious screened porch with outdoor dining...Read more

Location: 
Katama
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$2,200 - $4,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,000
8
9
10
11
12
13
14
$3,000
15
16
17
18
19
20
21
$3,000
22
23
24
25
26
27
28
$4,000
29
30
 $4,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
6
7
8
9
10
11
12
$5,000
13
14
15
16
17
18
19
$5,000
20
21
22
23
24
25
26
$5,300
27
28
29
30
31
 $5,300
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,300
3
4
5
6
7
8
9
$5,300
10
11
12
13
14
15
16
$5,300
17
18
19
20
21
22
23
$5,300
24
25
26
27
28
29
30
$4,300
31
 $3,350
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,350
7
8
9
10
11
12
13
$3,350
14
15
16
17
18
19
20
$3,000
21
22
23
24
25
26
27
$2,200
28
29
30
 $2,200
Clean Fee: 
$425; on two-week rentals $475; Interim cleaning upon request
Tax: State & Local: 
11.7

Rates just reduced for available weeks - see calendar for rates.

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Delightful Modern Cape, Large Deck Overlooks Private Yard, Central A/C, WiFi

House has exterior security camerasRead more

Location: 
Edgartown
Sleeps: 
7
Bedrooms: 
4
Baths: 
3
Price Range:
$2,700 - $4,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,700
8
9
10
11
12
13
14
$3,200
15
16
17
18
19
20
21
$3,200
22
23
24
25
26
27
28
$4,000
29
30
 $4,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
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
31
 $4,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,500
3
4
5
6
7
8
9
$5,500
10
11
12
13
14
15
16
$5,500
17
18
19
20
21
22
23
$5,500
24
25
26
27
28
29
30
$4,000
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
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
 $2,700
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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Sweet Cape Home, Gorgeous Water Views, Walk to Town, Lovely Landscaped Yard, Deck and Outdoor Dining Area.

Note: New Updates for 2025 Rental Season Season: New photos of the upgrades will not be posted until mid-January 2025:

2nd Level balcony/deck seen in photos removed so that primary bedroom...Read more

Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,200 - $4,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,000
8
9
10
11
12
13
14
$4,000
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,500
29
30
 $4,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,500
6
7
8
9
10
11
12
$4,500
13
14
15
16
17
18
19
$4,500
20
21
22
23
24
25
26
$4,500
27
28
29
30
31
 $5,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,000
3
4
5
6
7
8
9
$5,000
10
11
12
13
14
15
16
$5,000
17
18
19
20
21
22
23
$5,000
24
25
26
27
28
29
30
$5,000
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
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
28
29
30
 
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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Lovely Oak Bluffs Home, 3 Bedrooms, 2.5 Baths, Sleeps 7. Set just on the Outskirts of Oak Bluffs Center

Lovely 3 bedroom, 2.5 bath home that sleeps 7. This sweet home is bordered by a large yard and is located just on the outskirts of Oak Bluffs. The patio...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$2,500 - $4,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,950
8
9
10
11
12
13
14
$2,950
15
16
17
18
19
20
21
$2,950
22
23
24
25
26
27
28
$2,950
29
30
 $4,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,500
6
7
8
9
10
11
12
$4,500
13
14
15
16
17
18
19
$4,500
20
21
22
23
24
25
26
$4,500
27
28
29
30
31
 $4,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,500
3
4
5
6
7
8
9
$4,500
10
11
12
13
14
15
16
$4,500
17
18
19
20
21
22
23
$4,500
24
25
26
27
28
29
30
$4,000
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$3,200
14
15
16
17
18
19
20
$3,200
21
22
23
24
25
26
27
$3,000
28
29
30
 $2,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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Pristine Contemporary Saltbox Home set in a quiet area on the outskirts of Edgartown, 4 Bedrooms, 3 baths, Landscaped Yard with a Bluestone Patio with outdoor Dining and Grill area

This lovely home features open living, dining & kitchen areas on the first level. Additional living space in the sunny TV room features sofa & chair seating and opens via...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
4
Baths: 
3
Price Range:
$3,900 - $4,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
$3,900
15
16
17
18
19
20
21
$3,900
22
23
24
25
26
27
28
$4,200
29
30
 $5,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500
6
7
8
9
10
11
12
$5,500
13
14
15
16
17
18
19
$5,500
20
21
22
23
24
25
26
$5,500
27
28
29
30
31
 $6,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,500
3
4
5
6
7
8
9
$7,000
10
11
12
13
14
15
16
$5,500
17
18
19
20
21
22
23
$7,000
24
25
26
27
28
29
30
$5,500
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$3,900
14
15
16
17
18
19
20
$3,900
21
22
23
24
25
26
27
$3,900
28
29
30
 $3,900
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

4 night minimum stay ($850 per night) 7/19 to 7/24

 

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Classic Lovely Vineyard Cottage, Pristine Condition, Approximately 1.5 Miles to Town and Beaches. Mature Landscaped Yard, Spacious Deck

The Perfect Cozy Cottage, is pristinely maintained and situated in a quiet neighborhood just on the outskirts of Oak Bluffs.  This spacious 2 bedroom, 2 bath home sleeps 4. The...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,700 - $4,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,700
8
9
10
11
12
13
14
$2,700
15
16
17
18
19
20
21
$2,700
22
23
24
25
26
27
28
$2,900
29
30
 $3,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
6
7
8
9
10
11
12
$3,500
13
14
15
16
17
18
19
$3,500
20
21
22
23
24
25
26
$3,500
27
28
29
30
31
 $4,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,000
3
4
5
6
7
8
9
$4,000
10
11
12
13
14
15
16
$4,000
17
18
19
20
21
22
23
$4,000
24
25
26
27
28
29
30
$4,000
31
 $2,700
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,700
7
8
9
10
11
12
13
$2,700
14
15
16
17
18
19
20
$2,700
21
22
23
24
25
26
27
$2,700
28
29
30
 
Clean Fee: 
$300, additional may apply multiple week rentals
Tax: State & Local: 
11.7
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Newly Updated Chilmark Cottage, Key to Private association Black Point Beach just 8/10ths mile from Cottage

For those who love Chilmark! Located in a very private setting off of Quenames Rd, this fresh and modern updated cottage comes with a key to private association Black Point...Read more

Location: 
Chilmark
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$3,500 - $4,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,500
8
9
10
11
12
13
14
$3,500
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,000
29
30
 $5,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500
6
7
8
9
10
11
12
$5,500
13
14
15
16
17
18
19
$5,500
20
21
22
23
24
25
26
$5,500
27
28
29
30
31
 $5,750
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,750
3
4
5
6
7
8
9
$5,750
10
11
12
13
14
15
16
$5,750
17
18
19
20
21
22
23
$5,750
24
25
26
27
28
29
30
$5,750
31
 $5,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,000
7
8
9
10
11
12
13
$5,000
14
15
16
17
18
19
20
$4,500
21
22
23
24
25
26
27
$4,500
28
29
30
 $3,500
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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Charming, 4-bedroom Oak Bluffs Home, pristinely maintained!  The large wraparound porch and backyard patio areas provide the perfect venue for relaxing when not at the beach or out and about...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,000 - $4,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,500
8
9
10
11
12
13
14
$2,500
15
16
17
18
19
20
21
$2,500
22
23
24
25
26
27
28
$2,500
29
30
 $3,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
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
31
 $3,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,000
3
4
5
6
7
8
9
$5,000
10
11
12
13
14
15
16
$5,750
17
18
19
20
21
22
23
$5,750
24
25
26
27
28
29
30
$5,250
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$2,000
14
15
16
17
18
19
20
$2,000
21
22
23
24
25
26
27
$2,000
28
29
30
 $2,000
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

Parking for two cars only, no on-street parking!

 

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Charming & Cozy 2 Bedroom, 2 Bath Home, West Chop area of Vineyard Haven, Located on a Quiet Street, Close to Town & Beach

Ideally located in the West Chop woods area of Vineyard Haven, just 1 mile to town center and the business district, and a 10 to 15-minute drive to various public...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$3,650 - $4,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,850
8
9
10
11
12
13
14
$3,850
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,000
29
30
 $4,650
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,650
6
7
8
9
10
11
12
$4,850
13
14
15
16
17
18
19
$4,850
20
21
22
23
24
25
26
$4,850
27
28
29
30
31
 $4,850
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,850
3
4
5
6
7
8
9
$5,150
10
11
12
13
14
15
16
$5,150
17
18
19
20
21
22
23
$5,150
24
25
26
27
28
29
30
$5,150
31
 $3,300
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,300
7
8
9
10
11
12
13
$3,200
14
15
16
17
18
19
20
$3,200
21
22
23
24
25
26
27
$3,200
28
29
30
 $2,700
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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Spacious West Tisbury Home, Multiple Indoor, Outdoor living Spaces. 4 bedrooms, 5 Min Drive to Lambert's Cove Beach

Nestled off the serene Hidden Village Rd, merely 1.5 miles away from Lambert’s Cove Beach, this charming, spacious home offers contemporary comforts in a secluded haven. With a blend of...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,500 - $4,000
June 2025
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 2025
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
31
 
August 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
$8,000
10
11
12
13
14
15
16
$8,000
17
18
19
20
21
22
23
$8,500
24
25
26
27
28
29
30
$7,000
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$3,500
14
15
16
17
18
19
20
$3,500
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7

 

 

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SWEET 3-BEDROOM, 3-BATH CHILMARK COTTAGE, SPACIOUS SCREENED PORCH AND DECK AREAS, OUTDOOR SHOWER; PRIVATE LOCATION ON 4 ACRES, 10 MINUTES TO LUCY VINCENT AND LONG POINT BEACHES

Charming updated summer home features a dining room that seats six, well-stocked kitchen, living room, plus screen porch with ceiling fan, dining table and chairs for 8, and reading/lounging nooks, leading...Read more

Location: 
Chilmark
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$3,300 - $3,930
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,670
8
9
10
11
12
13
14
$3,670
15
16
17
18
19
20
21
$3,670
22
23
24
25
26
27
28
$3,670
29
30
 $3,780
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,780
6
7
8
9
10
11
12
$3,780
13
14
15
16
17
18
19
$3,780
20
21
22
23
24
25
26
$3,780
27
28
29
30
31
 $3,780
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,780
3
4
5
6
7
8
9
$3,930
10
11
12
13
14
15
16
$3,930
17
18
19
20
21
22
23
$3,930
24
25
26
27
28
29
30
$3,930
31
 $3,780
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,780
7
8
9
10
11
12
13
$3,780
14
15
16
17
18
19
20
$3,780
21
22
23
24
25
26
27
$3,780
28
29
30
 $3,780
Clean Fee: 
$300 per week, $200 interim cleaning on multiple week rentals
Tax: State & Local: 
11.7

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