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Victorian East Chop Cottage all Newly updated, 4 Bedrooms, 3.5 Baths, Main House and Detached Guest Suite

Nestled in the highly sought-after East Chop neighborhood of Oak Bluffs, this charming Victorian cottage offers the perfect blend of classic Vineyard character and modern comfort. Ideally located within walking...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,000 - $12,500
June 2027
SuMoTuWeThFrSaWeek
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$7,500
6
7
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12
$7,500
13
14
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$7,500
20
21
22
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24
25
26
$7,500
27
28
29
30
 $11,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$11,500
4
5
6
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10
$11,500
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12
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$12,500
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19
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$12,500
25
26
27
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29
30
31
$12,500
August 2027
SuMoTuWeThFrSaWeek
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$17,000
8
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11
12
13
14
$17,000
15
16
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20
21
$17,000
22
23
24
25
26
27
28
$12,500
29
30
31
 $10,000
September 2027
SuMoTuWeThFrSaWeek
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2
3
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$10,000
5
6
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$7,000
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$7,000
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20
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25
$7,000
26
27
28
29
30
 $6,000
Clean Fee: 
$500 per week
Tax: State & Local: 
14.45

 

 

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Updated East Chop Area Summer Retreat, Great Proximity to Town Center and Beaches, Cottage Styling with All the Modern Amenities, Central A/C. Covered Porch and Open Patio Areas.

Visitors will enjoy this delightful &  comfortable 4 bedroom, 3 bath home in the desirable East Chop area of Oak Bluffs. 

Relax in the breeze with your morning coffee on the front...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$0 - $0
June 2027
SuMoTuWeThFrSaWeek
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14
15
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26
27
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29
30
 $5,350
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,350
4
5
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10
$5,350
11
12
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$5,350
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19
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$5,350
25
26
27
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30
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$7,000
August 2027
SuMoTuWeThFrSaWeek
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$7,000
8
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11
12
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$7,200
15
16
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18
19
20
21
$7,500
22
23
24
25
26
27
28
$7,500
29
30
31
 
September 2027
SuMoTuWeThFrSa
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Clean Fee: 
$500 per week
Tax: State & Local: 
14.45
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Edgartown Retreat-Impeccably Maintained, Heated Pool -14 x 32', Screened Porch, Bluestone Patio, Exqusite Grounds and Gardens, Multiple Interior and Exterior Living Spaces

Nestled amidst picturesque grounds and gardens, this enchanting vacation getaway boasts an array of indoor and outdoor spaces seamlessly interconnected. The focal points of summer relaxation include a 14 x...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$8,000 - $15,000
June 2027
SuMoTuWeThFrSaWeek
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25
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$12,000
27
28
29
30
 $15,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$15,000
4
5
6
7
8
9
10
$15,000
11
12
13
14
15
16
17
$15,000
18
19
20
21
22
23
24
$15,000
25
26
27
28
29
30
31
$15,000
August 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
6
7
$15,000
8
9
10
11
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$15,000
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20
21
$15,000
22
23
24
25
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27
28
$11,000
29
30
31
 $8,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,000
5
6
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$8,000
12
13
14
15
16
17
18
19
20
21
22
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27
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29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Pool Heated to 81 degrees included in rental rate July & August weeks. 

Pool Heat shoulder season weeks additional propane surcharge, please inquire! 

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West Chop, Waterfront, Private Beach

Summer Compound in a majestic location.  Vintage vacation home perfect for large family gatherings.  Enjoy sweeping ocean views from the large comfortably furnished veranda.  A large screened porch offers seating...Read more

Location: 
Vineyard Haven
Sleeps: 
14
Bedrooms: 
6
Baths: 
2
Price Range:
$0 - $0
June 2027
SuMoTuWeThFrSaWeek
 1
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3
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12
13
14
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16
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20
21
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25
26
27
28
29
30
 $15,600
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$15,600
4
5
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10
$15,600
11
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$15,600
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24
$15,600
25
26
27
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30
31
$15,600
August 2027
SuMoTuWeThFrSaWeek
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$15,600
8
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$15,600
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$15,600
22
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$15,600
29
30
31
 
September 2027
SuMoTuWeThFrSa
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29
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Clean Fee: 
$875 per rental period
Tax: State & Local: 
11.7
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Charming , Modern In-Town Oak Bluffs Vacation Home. Walk to Town, Parks, Beach. 4 Bedrooms, Sleeps 8, 3 Baths

This charming Oak Bluffs home is tucked away in a peaceful neighborhood, yet conveniently located just a 10-minute walk to the heart of town, the harbor, and the beach. Meticulously...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$5,000 - $7,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
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7
8
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10
11
12
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$5,000
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21
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23
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25
26
$5,000
27
28
29
30
 $5,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,000
4
5
6
7
8
9
10
$6,500
11
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$6,000
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19
20
21
22
23
24
$6,500
25
26
27
28
29
30
31
$7,500
August 2027
SuMoTuWeThFrSaWeek
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2
3
4
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$9,500
8
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$9,500
15
16
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$9,500
22
23
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25
26
27
28
$6,500
29
30
31
 $5,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,000
5
6
7
8
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10
11
$5,000
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 $4,500
Clean Fee: 
$450 per week
Tax: State & Local: 
14.45
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Classic Updated Gingerbread Cottage, 5 Minute Stroll Along Harbor to Beach and Town Center,

Classic Vineyard Oak Bluffs Cottage, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. The main living level features a lovely kitchen, very well stocked with...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,500 - $7,500
June 2027
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
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25
26
$3,500
27
28
29
30
 $4,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
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$4,000
4
5
6
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9
10
$5,000
11
12
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$4,500
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19
20
21
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23
24
$4,500
25
26
27
28
29
30
31
$5,000
August 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
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$7,500
8
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$7,500
15
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$7,500
22
23
24
25
26
27
28
$7,500
29
30
31
 $4,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,500
5
6
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10
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$4,500
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15
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$3,500
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20
21
22
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24
25
$3,500
26
27
28
29
30
 $3,500
Clean Fee: 
$350 ($275 for interim cleaning on multiple week rentals)
Tax: State & Local: 
14.45
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Charming Newly Updated Menemsha Cottage, 2 + Bedroom Cottage Sleeps 5, AC, Screened Porch & Deck, Walk to Menemsha Village & Beach

Dreaming of Vacationing in an idyllic Menemsha Cottage? This adorable newly updated  1950s cottage nestled in the village area provides easy access to numerous exclusive Chilmark beaches with town permits and Menemsha Beach...Read more

Location: 
Chilmark
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$2,500 - $3,500
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$3,000
6
7
8
9
10
11
12
$3,000
13
14
15
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17
18
19
$3,000
20
21
22
23
24
25
26
$3,000
27
28
29
30
 $3,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,500
4
5
6
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10
$3,500
11
12
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$3,500
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19
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23
24
$3,500
25
26
27
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29
30
31
$3,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
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$3,500
8
9
10
11
12
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14
$3,500
15
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20
21
$3,500
22
23
24
25
26
27
28
$3,500
29
30
31
 $3,200
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,200
5
6
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$3,200
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$3,200
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25
$3,200
26
27
28
29
30
 
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7
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LIGHT FILLED CONTEMPORARY HOME, AC, DECK AND SUN PORCH, SLEEPS 8

Set on a quiet circular street (Teaberry Lane), on the outskirts of Edgartown. Bike paths at the end of the street connect to town and miles of touring trails. This...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$4,500 - $4,500
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSa
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August 2027
SuMoTuWeThFrSaWeek
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$4,500
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$4,500
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$4,500
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$4,500
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September 2027
SuMoTuWeThFrSa
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Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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Lovely Home in Island Grove Area of Edgartown Conveniently Located between South Beach and Edgartown Village. Association Tennis Courts and Pickleball Available to Renters

This recently updated home is tucked in the Island Grove area of Edgartown and is a perfect retreat for families & friends to gather. Located in a desirable neighborhood with access...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$5,000 - $6,060
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
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19
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25
26
$5,000
27
28
29
30
 $5,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,500
4
5
6
7
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9
10
$6,060
11
12
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$6,060
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$6,060
25
26
27
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30
31
$6,060
August 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
6
7
$6,800
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9
10
11
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14
$6,800
15
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20
21
$6,800
22
23
24
25
26
27
28
$6,800
29
30
31
 $5,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,000
5
6
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$5,000
12
13
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15
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18
$5,000
19
20
21
22
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25
$5,000
26
27
28
29
30
 $5,000
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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Contemporary, Spacious Home, Heated Pool,18 x 40, Luxury Amenities, Screened Porch, Patio and Private Yard

This beautiful new luxury home with an 18 x 40 heated pool which is located a quick bike ride to Morning Glory Farm and close to historic Edgartown Village, is...Read more

Location: 
Edgartown
Sleeps: 
12
Bedrooms: 
6
Baths: 
4
Price Range:
$6,500 - $17,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$9,000
6
7
8
9
10
11
12
$10,250
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14
15
16
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18
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$13,250
20
21
22
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25
26
$15,500
27
28
29
30
 $17,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$17,500
4
5
6
7
8
9
10
$17,500
11
12
13
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$17,500
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19
20
21
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23
24
$18,000
25
26
27
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29
30
31
$18,250
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$18,750
8
9
10
11
12
13
14
$18,750
15
16
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18
19
20
21
$18,750
22
23
24
25
26
27
28
$16,500
29
30
31
 $12,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$12,000
5
6
7
8
9
10
11
$8,500
12
13
14
15
16
17
18
$7,500
19
20
21
22
23
24
25
$7,000
26
27
28
29
30
 $6,750
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

Pool is heated to 82 degrees in July and August included in rental rate. 

 

Pool heat fee May (after 5/15), June, Sept $350 per week. Pool heated to 82.

 

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