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Beautiful Oak Bluffs Home, Screened Porch & Open Porch, Association Tennis Courts, 4 bedrooms, 3.5 baths, Ideally Located just 2 miles to Town and Beach

Spacious contemporary home nestled in the lovely community of homes Meadow View Farms just on the outskirts of Oak Bluffs and 2 miles to town center and Oak Bluffs beaches....Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$8,000 - $12,500
June 2027
SuMoTuWeThFrSaWeek
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$9,000
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 $9,000
July 2027
SuMoTuWeThFrSaWeek
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$9,000
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$9,000
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$9,000
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$12,500
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$12,500
August 2027
SuMoTuWeThFrSaWeek
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$12,500
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$12,500
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$12,500
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$12,500
29
30
31
 $12,500
September 2027
SuMoTuWeThFrSaWeek
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2
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$12,500
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$12,500
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$8,500
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$8,500
26
27
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29
30
 $8,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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KATAMA AREA, SET ON PRIVATE ACREAGE, SHORT DRIVE TO SOUTH BEACH AND EDGARTOWN VILLAGE CENTER

Extended family will enjoy the comfort and private setting of this large 5 bedroom home in the Katama area of Edgartown.   Spacious for extended family, the kitchen with custom cabinetry and...Read more

Location: 
Katama
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$2,400 - $6,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,400
6
7
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12
$3,400
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19
$4,000
20
21
22
23
24
25
26
$5,100
27
28
29
30
 $5,400
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,400
4
5
6
7
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9
10
$5,800
11
12
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$6,200
18
19
20
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$6,200
25
26
27
28
29
30
31
$6,500
August 2027
SuMoTuWeThFrSaWeek
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2
3
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$6,500
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$6,500
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$6,500
22
23
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25
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27
28
$5,200
29
30
31
 $4,800
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,800
5
6
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$3,400
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$3,000
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$3,000
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29
30
 $3,000
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
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Eagles Nest, Set on a Quiet Cul-de-Sac, Large Deck, Central A/C

Lovely open concept 3 bedroom, 2 full bath home on a quiet cul de sac in popular Dodger’s Hole neighborhood, steps to bike paths, and public transportation.  Dodger’s Hole is centrally...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,700 - $3,700
June 2027
SuMoTuWeThFrSaWeek
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29
30
 $3,700
July 2027
SuMoTuWeThFrSaWeek
 1
2
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$3,700
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10
$3,700
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$3,700
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$3,700
25
26
27
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29
30
31
$3,900
August 2027
SuMoTuWeThFrSaWeek
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2
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$3,900
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$4,100
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$4,100
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$3,900
29
30
31
 $3,700
September 2027
SuMoTuWeThFrSaWeek
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$3,700
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30
 
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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Beautiful Newly Updated Oak Bluffs Home, Nestled on a Large Landscaped Lot in a Quiet Enclave of Homes. 4 Bedrooms. 4.5 Baths

Step inside to discover a welcoming interior, highlighted by a sunroom featuring comfortable seating around the TV. The open first-floor plan seamlessly integrates the main family room complete with a media...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,000 - $15,000
June 2027
SuMoTuWeThFrSaWeek
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2
3
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5
$6,000
6
7
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12
$6,500
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14
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19
$7,500
20
21
22
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25
26
$7,500
27
28
29
30
 $8,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$8,500
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5
6
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10
$8,500
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$8,500
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$9,000
25
26
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30
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$10,000
August 2027
SuMoTuWeThFrSaWeek
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$15,000
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$16,000
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$16,000
22
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$10,000
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30
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 $7,000
September 2027
SuMoTuWeThFrSaWeek
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$7,000
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$6,000
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$6,000
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$6,000
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30
 $6,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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Beautiful Upscale Contemporary Home, Designer Details Throughout, 4 Bedrooms, 4.5 Baths, Muliple Living Areas

Discover this stunning tri-level vacation home nestled in a peaceful community just on the outskirts of Oak Bluffs and minutes away from Oak Bluffs center, Edgartown Village, downtown Vineyard Haven, and several...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
4
Price Range:
$8,300 - $8,750
June 2027
SuMoTuWeThFrSaWeek
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 $8,300
July 2027
SuMoTuWeThFrSaWeek
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2
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$8,300
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$8,500
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$8,500
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$8,750
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31
August 2027
SuMoTuWeThFrSaWeek
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$9,900
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$9,900
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$8,750
29
30
31
 
September 2027
SuMoTuWeThFrSa
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25
26
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29
30
 
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
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Newly Refurbished Contemporary Home, Beautifully Furnished, Privately Situated with Large Yard and Wraparound Farmer’s Porch, Dodger’s Hole Area

A great vacation begins with a great vacation home. This spacious home set on a private, large landscaped lot is sure to please. The summer wrap around porch is the perfect...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$6,550 - $7,900
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,500
6
7
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12
$7,500
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$7,500
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21
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$7,500
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28
29
30
 $7,700
July 2027
SuMoTuWeThFrSaWeek
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2
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$7,700
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$7,700
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$7,700
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19
20
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22
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24
$7,700
25
26
27
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29
30
31
$7,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
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$7,900
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9
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$7,900
15
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21
$7,900
22
23
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25
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28
$7,900
29
30
31
 $7,300
September 2027
SuMoTuWeThFrSaWeek
 1
2
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4
$7,300
5
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$7,300
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$7,300
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25
$7,300
26
27
28
29
30
 $7,300
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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Katama Area, Stylish Designer Luxury, Bike to South Beach and Village Areas, Spacious Bluestone Patio overlooks Private Yard Area

All newly renovated and beautifully furnished, the main level of this traditional style floor plan includes, - hardwood floors throughout, bead board accents, a living room with balcony, TV center,...Read more

Location: 
Katama
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,000 - $4,800
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSa
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August 2027
SuMoTuWeThFrSa
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September 2027
SuMoTuWeThFrSa
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25
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29
30
 
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

Owner maintains a 2 week minimum stay from mid-June to 2nd week in September.

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Spectacular all new Harborfront Retreat, Heated Pool, Spacious Patio & Deck Areas, Stunning Views of Edgartown Harbor

Village center finely crafted custom home, harbor front, heated pool, refined decor and luxury amenities. Spectacular water views across the decks, patio, and pool to the harbor from most of the living...Read more

Location: 
Edgartown
Sleeps: 
10
Bedrooms: 
5
Baths: 
6
Price Range:
$18,000 - $58,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$25,000
6
7
8
9
10
11
12
$25,000
13
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$46,000
20
21
22
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25
26
$58,000
27
28
29
30
 $58,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$58,000
4
5
6
7
8
9
10
$58,000
11
12
13
14
15
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17
$58,000
18
19
20
21
22
23
24
$58,000
25
26
27
28
29
30
31
$58,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$58,000
8
9
10
11
12
13
14
$58,000
15
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19
20
21
$58,000
22
23
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25
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27
28
$58,000
29
30
31
 $58,000
September 2027
SuMoTuWeThFrSaWeek
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2
3
4
$58,000
5
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$39,000
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18
$39,000
19
20
21
22
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24
25
$18,000
26
27
28
29
30
 $18,000
Clean Fee: 
$1200 per week
Tax: State & Local: 
11.7

 

 

 

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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:
$0 - $0
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,500
6
7
8
9
10
11
12
$9,500
13
14
15
16
17
18
19
$9,500
20
21
22
23
24
25
26
$10,000
27
28
29
30
 $10,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$10,500
4
5
6
7
8
9
10
$10,500
11
12
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$10,500
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19
20
21
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23
24
$10,500
25
26
27
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29
30
31
$10,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$10,500
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9
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14
$10,500
15
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21
$10,500
22
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25
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27
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$10,500
29
30
31
 $9,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,500
5
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$9,500
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13
14
15
16
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18
19
20
21
22
23
24
25
26
27
28
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 $500 per week surcharge.

 

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Water Views, Heated Pool , Walk/Drive to Private Association Makonikey Beach, 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:
$9,500 - $14,750
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$14,750
6
7
8
9
10
11
12
$14,750
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14
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18
19
$14,750
20
21
22
23
24
25
26
$14,750
27
28
29
30
 $14,750
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$14,750
4
5
6
7
8
9
10
$14,750
11
12
13
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15
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17
$14,750
18
19
20
21
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23
24
$14,750
25
26
27
28
29
30
31
$14,750
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$14,750
8
9
10
11
12
13
14
$14,750
15
16
17
18
19
20
21
$14,750
22
23
24
25
26
27
28
$14,750
29
30
31
 $14,750
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$14,750
5
6
7
8
9
10
11
$14,750
12
13
14
15
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18
$14,750
19
20
21
22
23
24
25
$14,750
26
27
28
29
30
 $14,750
Clean Fee: 
$750 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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