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Long Point Beach Area, Heated Pool, Large Patio with Living and Dining Areas, Gorgeous Contemporary Coastal Interior, Large Private Yard

Gorgeous all newly updated 4 bedroom home with central AC, privately tucked away in the Long Point Beach area of West Tisbury, a family-friendly community of lovely homes, and only minutes away...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$7,500 - $10,500
June 2026
SuMoTuWeThFrSaWeek
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$7,500
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$9,500
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$9,500
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$10,000
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 $10,500
July 2026
SuMoTuWeThFrSaWeek
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$10,500
5
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$10,500
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$10,500
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$10,500
26
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30
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 $10,500
August 2026
SuMoTuWeThFrSaWeek
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$10,500
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$10,500
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$10,500
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$10,500
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$10,500
30
31
 $9,500
September 2026
SuMoTuWeThFrSaWeek
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2
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$9,500
6
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$9,500
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29
30
 
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

Pool heated by aqua-solar panels throughout the rental period.  Specific request for 82 degrees by use of propane heat incurs a $400 per week surcharge.

 

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REIDM

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Property Details
Water Views, Heated Pool , Walk/Drive to Private Association Waterfront, North Shore, Breathtaking Sunsets, Sleeps 8.

Looking to escape? This pristine contemporary home has it all; beautiful distant ocean views, a heated pool, a gorgeous pool house, patio dining and grill area poolside with an expansive deck the full width of...Read more

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

Pool Heated to 81, included in Rental Rate last Saturday in June to end of August 

 

Pool Heated to 81 June and September weeks ( begins last Saturday in August), additional $300 propane surcharge per week

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REINJ

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Property Details
Gorgeous Katama Home, Heated Pool, Large Private Pool Patio and Landscaped Yard, Screened Porch and Expansive Deck, Located Just one mile to South Beach

Gorgeous home in the Katama area of Edgartown with a heated pool.  Ideally situated midway between South Beach and Edgartown village area!  Bike paths at the end of the street provide an easy bike ride...Read more

Location: 
Katama
Sleeps: 
10
Bedrooms: 
5
Baths: 
4
Price Range:
$0 - $0
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: 
$750 per week
Tax: State & Local: 
11.7

 Pool heat included in rental rate in July & August

June and September pool heat is an additional cost to the renter of $300 per week

 

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RIORE

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Property Details
Close to Edgartown Center and Beaches, Bike Paths 2/10 mile from house, Large and Private Deck, Central AC

This lovely 3 bedroom, 2.5 bath home features open concept living, dining, and kitchen areas. The spacious living and dining area opens via glass sliders to a large and private 20 x 40 ft...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$4,200 - $4,900
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
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5
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$4,000
7
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$4,000
14
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$4,000
21
22
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27
$4,000
28
29
30
 $4,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,700
5
6
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$4,700
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$4,700
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25
$4,700
26
27
28
29
30
31
 $4,700
August 2026
SuMoTuWeThFrSaWeek
 1
$4,700
2
3
4
5
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$4,900
9
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$4,900
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$4,900
23
24
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28
29
$4,700
30
31
 $4,200
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
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5
$4,200
6
7
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29
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Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

 

 

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ROB59

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Property Details
Luxurious Home, Privately Situated in the West Chop Area of Vineyard Haven, Heated Pool, North Shore Waterviews, Multiple Indoor/Outdoor LIving Spaces. 6 Bedrooms, 5.5 Baths Sleeps 13.

Exceptional Rental Offering: Stunning 6-Bedroom, 5.5-Bath Home in West Chop, Vineyard Haven

Experience the epitome of summer luxury living in this exquisite 6-bedroom, 5.5-bath home nestled in the desirable West...Read more

Location: 
Vineyard Haven
Sleeps: 
13
Bedrooms: 
6
Baths: 
5
Price Range:
$14,000 - $35,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
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 $25,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$25,000
5
6
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$25,000
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$30,000
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$30,000
26
27
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30
31
 $35,000
August 2026
SuMoTuWeThFrSaWeek
 1
$35,000
2
3
4
5
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7
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$35,000
9
10
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13
14
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$35,000
16
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$35,000
23
24
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28
29
$35,000
30
31
 $25,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$25,000
6
7
8
9
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11
12
$18,000
13
14
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$18,000
20
21
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23
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25
26
$16,000
27
28
29
30
 $14,000
Clean Fee: 
$1750 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
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2
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July 2026
SuMoTuWeThFrSaWeek
 1
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30
31
 $15,000
August 2026
SuMoTuWeThFrSaWeek
 1
$15,000
2
3
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$13,000
9
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$13,000
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$13,000
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30
31
 
September 2026
SuMoTuWeThFrSa
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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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ROBER

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Property Details
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 - $3,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,700
7
8
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13
$2,700
14
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$2,700
21
22
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27
$3,000
28
29
30
 $3,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,500
5
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$3,500
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$3,500
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$3,500
26
27
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30
31
 $3,500
August 2026
SuMoTuWeThFrSaWeek
 1
$3,500
2
3
4
5
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$3,500
9
10
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$3,500
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17
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$3,500
23
24
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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
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18
19
$2,500
20
21
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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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ROBIH

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Property Details
Seaview Condo Unit, Gorgeous Water Views, In Town Location, Modern updated Interior!

Note: Seavies 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...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,100 - $5,600
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,150
7
8
9
10
11
12
13
$2,150
14
15
16
17
18
19
20
$2,550
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
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12
$2,500
13
14
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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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ROCHA

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Property Details
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:
$5,100 - $5,100
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
$5,100
14
15
16
17
18
19
20
21
22
23
24
25
26
27
$5,900
28
29
30
 $5,900
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,900
5
6
7
8
9
10
11
$5,900
12
13
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15
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18
$5,900
19
20
21
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25
$5,900
26
27
28
29
30
31
 $5,900
August 2026
SuMoTuWeThFrSaWeek
 1
$5,900
2
3
4
5
6
7
8
$6,500
9
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15
$6,500
16
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$6,500
23
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$6,500
30
31
 
September 2026
SuMoTuWeThFrSa
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2
3
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9
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14
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17
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19
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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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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