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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:
$6,800 - $7,200
June 2026
SuMoTuWeThFrSaWeek
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$6,800
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$6,800
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$6,800
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$6,800
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 $6,900
July 2026
SuMoTuWeThFrSaWeek
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$6,900
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$6,900
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$6,900
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$6,900
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 $6,900
August 2026
SuMoTuWeThFrSaWeek
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$6,900
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$7,900
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$7,900
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$7,900
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$7,900
30
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 $7,200
September 2026
SuMoTuWeThFrSaWeek
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$7,200
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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:
$5,500 - $15,000
June 2026
SuMoTuWeThFrSaWeek
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$10,000
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$10,000
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$10,000
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$13,000
28
29
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 $15,000
July 2026
SuMoTuWeThFrSaWeek
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$15,000
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$15,000
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$15,000
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$15,000
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 $15,000
August 2026
SuMoTuWeThFrSaWeek
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$15,000
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 $11,000
September 2026
SuMoTuWeThFrSaWeek
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$11,000
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$11,000
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$11,000
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$11,000
27
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29
30
 $10,000
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:
$70 - $5,000
June 2026
SuMoTuWeThFrSaWeek
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 $4,000
July 2026
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$4,500
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$4,000
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30
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 $5,000
August 2026
SuMoTuWeThFrSaWeek
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$5,000
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$5,000
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$4,000
30
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 $4,000
September 2026
SuMoTuWeThFrSaWeek
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$4,000
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Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

Ferry Tickets for Purchase, 7/26- 8/2 & 8/23- 8/30  Please inquire! 

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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 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: 
$600
Tax: State & Local: 
11.7
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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 - $3,800
June 2026
SuMoTuWeThFrSaWeek
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$3,500
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$3,500
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$3,500
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$3,500
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 $3,800
July 2026
SuMoTuWeThFrSaWeek
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2
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$3,800
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$3,800
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$3,800
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 $4,000
August 2026
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$4,000
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$4,200
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$4,200
30
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 $3,000
September 2026
SuMoTuWeThFrSaWeek
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2
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$3,000
6
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$3,000
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$3,000
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$3,000
27
28
29
30
 
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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WILSL

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Property Details
New Gorgeous Contemporary Colonial Home, 4 bedrooms, 4.5 Baths, Sleeps 8, Spacious Yard Area, Deck Dining & Patio Area

Please note exterior photos to follow within 2 weeks. Tucked away on a half-acre at the end of a quiet lane just outside Edgartown, this exquisite coastal contemporary Colonial offers a...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$70 - $10,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
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9
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$10,000
14
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20
$10,000
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22
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27
$10,000
28
29
30
 $12,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$12,000
5
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$12,000
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$12,000
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$12,000
26
27
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30
31
 $14,000
August 2026
SuMoTuWeThFrSaWeek
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$14,000
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$14,000
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$16,000
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$14,000
23
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$14,000
30
31
 $10,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
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5
$10,000
6
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$10,000
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$10,000
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21
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$10,000
27
28
29
30
 $10,000
Clean Fee: 
$620
Tax: State & Local: 
11.7

Ferry tickets for purchase, 7/12-7/19  - please inquire  (mv)

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WINGR

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Property Details
Designer Luxury with Oustanding Atlantic Ocean Views, Private Beaches, Squibnocket Farm Gated Community

Dramatic ocean views, idyllic one-of-a-kind location in a gated community, and private ocean beaches are but a few of the desirable features of this beautiful 5 bedroom, 5 bath contemporary home,...Read more

Location: 
Chilmark
Sleeps: 
10
Bedrooms: 
5
Baths: 
5
Price Range:
$30,000 - $45,000
June 2026
SuMoTuWeThFrSaWeek
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2
3
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$35,000
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$35,000
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$35,000
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$35,000
28
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 $40,000
July 2026
SuMoTuWeThFrSaWeek
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2
3
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$40,000
5
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$40,000
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$40,000
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$40,000
26
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30
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 $45,000
August 2026
SuMoTuWeThFrSaWeek
 1
$45,000
2
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$45,000
9
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$45,000
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$45,000
23
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$45,000
30
31
 $45,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$45,000
6
7
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$30,000
13
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$30,000
20
21
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25
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$30,000
27
28
29
30
 $30,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Ferry ticket avilable for purchase, 8/15 - 8/22  - please inquire   (mv)

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WOODJ

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Property Details
Gorgeous Retreat, Pool 18 X 36', Lush Landscaped Yard, Expansive Deck & Patio Areas, Luxury Interior, Media Room, Lambert's Cove Beach 1/2 mile

Gather your family, this gorgeous 5 bedroom home offers all one could want in a vacation home on the Vineyard. Resort-like outdoor amenities include a pool, stone patio surround, large deck with...Read more

Location: 
West Tisbury
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$6,600 - $8,700
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,100
7
8
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10
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12
13
$7,100
14
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20
$7,100
21
22
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27
$7,900
28
29
30
 $8,700
July 2026
SuMoTuWeThFrSaWeek
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2
3
4
$8,700
5
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7
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$8,700
12
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$8,700
19
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25
$9,400
26
27
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30
31
 $9,400
August 2026
SuMoTuWeThFrSaWeek
 1
$9,400
2
3
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5
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$9,400
9
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$9,400
16
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$9,400
23
24
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28
29
$9,400
30
31
 $4,700
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,700
6
7
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12
$6,600
13
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$6,600
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21
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25
26
$6,600
27
28
29
30
 
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7
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WOODO

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Property Details
Weku House, Luxury Living, Features Outstanding Entertainment Level, Guest Apartment, Custom Interior and Coastal Design

The Weku House is a luxury, 5,000 square foot home located in Oak Bluffs. Elegantly decorated with designer furnishings and interior appointments, the meticulous attention to detail makes this home a unique vacation retreat. With a total of 5 bedrooms and 5 1/2 baths, the home...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
5
Price Range:
$16,500 - $19,500
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSa
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August 2026
SuMoTuWeThFrSaWeek
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$19,500
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$16,500
30
31
 
September 2026
SuMoTuWeThFrSa
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30
 
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
Add Favorite
 
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YAEGM

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Property Details
Field Club, Exquisite New Luxury Home Offering Large Heated Pool, Pool House, Expansive Patio Area, Ideally located between Village Area and South Beach

Situated in one of the Island’s most sought-after Edgartown communities in Katama, this outstanding 5 bedroom, 6 bath luxury residence is located within the Field Club’s manicured grounds and features exceptional amenities as...Read more

Location: 
Katama
Sleeps: 
10
Bedrooms: 
5
Baths: 
6
Price Range:
$27,000 - $28,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$28,000
7
8
9
10
11
12
13
$28,000
14
15
16
17
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19
20
$28,000
21
22
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27
$28,000
28
29
30
 $29,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$29,000
5
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7
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11
$29,000
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$30,000
19
20
21
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24
25
$30,000
26
27
28
29
30
31
 $30,000
August 2026
SuMoTuWeThFrSaWeek
 1
$30,000
2
3
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6
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8
$32,000
9
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15
$32,000
16
17
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21
22
$32,000
23
24
25
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27
28
29
$30,000
30
31
 $28,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$28,000
6
7
8
9
10
11
12
$27,000
13
14
15
16
17
18
19
$27,000
20
21
22
23
24
25
26
$27,000
27
28
29
30
 $27,000
Clean Fee: 
$800 per week
Tax: State & Local: 
11.7

Pool Heated to 82 July & August weeks included in rental rate.

Pool Heated to 82 June & September weeks additional propane surcharge $275 per week. 

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