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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 2027
SuMoTuWeThFrSaWeek
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 $7,300
July 2027
SuMoTuWeThFrSaWeek
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$7,300
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$7,300
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$7,300
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$7,300
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$7,300
August 2027
SuMoTuWeThFrSaWeek
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$7,300
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$7,300
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$7,300
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$7,300
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30
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 $7,300
September 2027
SuMoTuWeThFrSaWeek
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$7,300
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Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

Owner open to renting with weekday arrival and departure in August to accommodate the need for car reservations. 

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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 - $7,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,500
6
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12
$9,000
13
14
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18
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$10,500
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21
22
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25
26
$12,500
27
28
29
30
 $14,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$14,000
4
5
6
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9
10
$17,500
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$17,500
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$17,500
25
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30
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$18,000
August 2027
SuMoTuWeThFrSaWeek
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$18,000
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$18,000
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$18,000
22
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$14,000
29
30
31
 $10,500
September 2027
SuMoTuWeThFrSaWeek
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$10,500
5
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$9,200
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$7,500
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$7,500
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30
 $7,500
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

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:
$7,000 - $14,000
June 2027
SuMoTuWeThFrSaWeek
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$8,000
6
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$8,000
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$9,000
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$10,000
27
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29
30
 $12,000
July 2027
SuMoTuWeThFrSaWeek
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$12,000
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$13,000
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$14,000
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$14,000
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$15,000
August 2027
SuMoTuWeThFrSaWeek
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$22,000
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$22,000
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$22,000
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$14,000
29
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 $9,500
September 2027
SuMoTuWeThFrSaWeek
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$9,500
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$8,000
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$8,500
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$8,500
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29
30
 $7,000
Clean Fee: 
$550
Tax: State & Local: 
11.7
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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 - $12,800
June 2027
SuMoTuWeThFrSaWeek
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$8,500
6
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$8,500
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$8,500
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$11,000
27
28
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30
 $12,400
July 2027
SuMoTuWeThFrSaWeek
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$12,400
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$12,400
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$12,400
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$12,400
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$12,400
August 2027
SuMoTuWeThFrSaWeek
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$12,800
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$12,800
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$12,800
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$11,800
29
30
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 $9,000
September 2027
SuMoTuWeThFrSaWeek
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$9,000
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$9,000
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$9,000
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$9,000
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 $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:
$5,300 - $12,000
June 2027
SuMoTuWeThFrSaWeek
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$6,500
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$7,500
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 $8,000
July 2027
SuMoTuWeThFrSaWeek
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$8,000
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$8,500
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$9,000
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$10,000
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$10,000
August 2027
SuMoTuWeThFrSaWeek
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$10,000
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$14,000
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$14,000
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$12,000
29
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 $8,500
September 2027
SuMoTuWeThFrSaWeek
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$8,500
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$6,300
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$5,300
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$5,300
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30
 $5,300
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
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WHARG

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Property Details
Lovely Home in a quiet Neighborhood. Walk to Town Center and Inkwell Beach, Large Private Deck, Room AC

Spacious sun-filled contemporary home located on a quiet private street, a 10-minute walk to town center, Inkwell Beach, and the harborfront.

The first level features a spacious kitchen with stainless steel...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$7,200 - $8,500
June 2027
SuMoTuWeThFrSaWeek
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$7,200
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$7,200
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$7,200
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$7,200
27
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29
30
 $7,200
July 2027
SuMoTuWeThFrSaWeek
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2
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$7,200
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$7,500
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$7,500
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$7,500
25
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$7,500
August 2027
SuMoTuWeThFrSaWeek
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$8,500
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$8,500
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$8,500
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$8,500
29
30
31
 $8,500
September 2027
SuMoTuWeThFrSaWeek
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$8,500
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29
30
 
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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WIL14

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Property Details

Classic updated 7 bedrooms, 5 bath West Chop Home. Nestled on a large landscaped lot on Hatch Rd in Vineyard Haven this spacious home offers the best in vacation home...Read more

Location: 
Vineyard Haven
Sleeps: 
12
Bedrooms: 
7
Baths: 
5
Price Range:
$10,000 - $11,000
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$1000 per week
Tax: State & Local: 
11.7
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WILCM

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Property Details
Hidden Cove Retreat, Walk to Association Tennis/Pickleball Courts, 3 Bedrooms, 2.5 Baths, Screened Porch and Deck

Nestled in the charming Hidden Cove community, this adorable contemporary home resides on a tranquil street within walking distance of the association's tennis/pickleball courts. Its central location places it just a...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$4,000 - $4,500
June 2027
SuMoTuWeThFrSaWeek
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2
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30
 $4,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,500
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5
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9
10
$4,500
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$4,500
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$4,500
25
26
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30
31
$4,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
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$6,500
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9
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$6,500
15
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21
$5,000
22
23
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25
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27
28
$5,000
29
30
31
 $4,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,000
5
6
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29
30
 
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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WILLC

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Property Details
Beautiful, Spacious Contemporary Home, Sleeps 8, Tucked on a large lot in an Enclave of Lovely Homes

Nestled amidst  lovely landscaped grounds, this contemporary vacation getaway offers ample space and modern comforts. A serene path from the backyard invites exploration of nearby walking trails. Boasting multiple living areas...Read more

Location: 
Edgartown
Sleeps: 
9
Bedrooms: 
4
Baths: 
3
Price Range:
$0 - $0
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$600
Tax: State & Local: 
11.7
Add Favorite
 
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WILLD

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Property Details
The Sweetest In-town Cottage! 2 Minute Walk to Main St

This adorable cottage-style home features 2 bedrooms, and 2 baths and is tucked in on a tiny side street off of Main St. Walk to all that the village center...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$3,000 - $4,200
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$3,700
6
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12
$3,700
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$3,700
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25
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$3,700
27
28
29
30
 $4,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,000
4
5
6
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9
10
$4,000
11
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$4,000
18
19
20
21
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23
24
$4,000
25
26
27
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29
30
31
$4,200
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,200
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9
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12
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14
$4,200
15
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20
21
$4,400
22
23
24
25
26
27
28
$4,400
29
30
31
 $3,000
September 2027
SuMoTuWeThFrSaWeek
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2
3
4
$3,000
5
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$3,000
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13
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15
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$3,000
19
20
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24
25
$3,000
26
27
28
29
30
 
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7

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