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Charming Post & Beam Home, Tucked on a Private Lot in the Desirable Makonikey Community of Homes, Walk to Private Association Beach, Multiple Indoor/Outdoor Living Spaces .

Rate just reduced by $700 8/1 to 8/8 week. 

Note: New for 2026. 

Two of the baths seen in current photos are being gutted and all newly updated. Walk-in glass showers in both, a...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$8,300 - $8,800
June 2027
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July 2027
SuMoTuWeThFrSaWeek
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$8,300
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$8,300
August 2027
SuMoTuWeThFrSaWeek
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$8,800
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$8,800
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September 2027
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Clean Fee: 
$575 per week
Tax: State & Local: 
11.7

 

 

 

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Distinctive Luxury Retreat Edgartown, Heated Saltwater Pool, 36 x 19', Pickle Ball Court

Luxurious Custom Crafted Edgartown Home, featuring Outstanding Outdoor Living Spaces with a Heated Saltwater Gunite Pool and Stone Patio Surround, Spa, Pickle Ball Court, Outdoor Kitchen & Grill area,  Outdoor Deck...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
4
Price Range:
$20,000 - $36,000
June 2027
SuMoTuWeThFrSaWeek
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3
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$21,000
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21
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$29,000
27
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29
30
 $29,000
July 2027
SuMoTuWeThFrSaWeek
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2
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$29,000
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$29,000
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$29,000
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$33,000
25
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$33,000
August 2027
SuMoTuWeThFrSaWeek
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$36,000
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$36,000
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$36,000
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$36,000
29
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 $33,000
September 2027
SuMoTuWeThFrSaWeek
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$33,000
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$21,000
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$21,000
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$21,000
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29
30
 
Clean Fee: 
$1400 per week
Tax: State & Local: 
11.7

Pool and Spa heated to 101 degrees, 4 to 8 pm daily July & August included in Rental Rate.  Four hour period can be changed upon request.

 

Pool and Spa Heated to 101 degrees, 4 to 8 pm June & Sept weeks additional $500 propane surcharge per week.  Spa in the Pool is only heated to the same temperature as the pool if no request for the Spa heat.  

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Light House is a Luxurious Harborfront Home and Part of a 2 House Compound Village Center, Walk to Light House and Fuller St Beaches

The Light House is part of a two-house luxury compound located waterfront on spectacular Edgartown Harbor with stunning views.  This unique residence was designed by one of the Island's leading architectural designers and has...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$10,000 - $30,000
June 2027
SuMoTuWeThFrSaWeek
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$15,000
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$20,000
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$20,000
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21
22
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$25,000
27
28
29
30
 $30,000
July 2027
SuMoTuWeThFrSaWeek
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$30,000
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$30,000
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$30,000
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$30,000
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$30,000
August 2027
SuMoTuWeThFrSaWeek
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$30,000
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$30,000
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$30,000
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$30,000
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 $30,000
September 2027
SuMoTuWeThFrSaWeek
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$30,000
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$25,000
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$25,000
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$25,000
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 $15,000
Clean Fee: 
$1000 per week
Tax: State & Local: 
11.7

 

 

 

 

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THE FERRY HOUSE IS A LUXURIOUS HARBORFRONT HOME, AND PART OF A 2 HOUSE COMPOUND, VILLAGE CENTER, WALK TO LIGHT HOUSE AND FULLER ST BEACHES

Welcome to luxury living dockside in this spectacular 3 bedroom, 3 bath restored boathouse.  The Ferry House has been featured in Architectural Digest.  Attention to detail, design, and craftsmanship are evident...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$10,000 - $25,000
June 2027
SuMoTuWeThFrSaWeek
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$15,000
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$20,000
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$20,000
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$25,000
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 $25,000
July 2027
SuMoTuWeThFrSaWeek
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$25,000
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$25,000
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$25,000
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$25,000
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$25,000
August 2027
SuMoTuWeThFrSaWeek
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$25,000
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$25,000
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$25,000
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$25,000
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 $25,000
September 2027
SuMoTuWeThFrSaWeek
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$25,000
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$20,000
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$20,000
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$20,000
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 $15,000
Clean Fee: 
$1000 per week
Tax: State & Local: 
11.7

 

 

 

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Stunning New 7 Bedroom Luxury Home, 7 baths, Heated Saltwater Pool, Multiple Decks, Screened Porch, Waterview, on the Edgartown Great Pond, Kayak to Private Association Beach on the South Shore

Experience unparalleled luxury in this newly completed, stunning home nestled on 9 acres along the serene Great Pond. Enjoy exclusive access to the Edgartown Great Pond perfect for kayaking. Owner provides...Read more

Location: 
Edgartown
Sleeps: 
14
Bedrooms: 
7
Baths: 
7
Price Range:
$29,000 - $42,500
June 2027
SuMoTuWeThFrSaWeek
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$29,000
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$29,000
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$29,000
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$29,000
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 $42,500
July 2027
SuMoTuWeThFrSaWeek
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$42,500
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$42,500
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$42,500
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$42,500
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$42,500
August 2027
SuMoTuWeThFrSaWeek
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$49,000
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$49,000
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$49,000
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$49,000
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 $29,000
September 2027
SuMoTuWeThFrSaWeek
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$29,000
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$29,000
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29
30
 
Clean Fee: 
$1500 per week
Tax: State & Local: 
11.7

Pool Heated to 82,  July & August included in rental rate. Last Saturday in June until last weekend of August.

Spa is on 6 to 10 pm at 101 degrees in July & August, additional times upon request

Pool Heated to 82, May, June, September, October, additional propane fee $350 per week. 

Spa, May, June, September can be turned on by owner for 3 or 4 hours per day at additional cost, inquire with agent! 

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Stunning Luxury Home, Heated 18 x 42 Gunite Pool, Spectacular Yard & Patio Areas, Ideally Located with a 10 minute Walk to Village, 7 minute drive to South Beach

Contemporary, architect-designed coastal-style farmhouse, this luxurious vacation home will exceed your every expectation in amenity, quality, furnishings, and location. Situated in a distinctive enclave of eight luxury homes on 1-2...Read more

Location: 
Edgartown
Sleeps: 
9
Bedrooms: 
5
Baths: 
5
Price Range:
$14,000 - $14,000
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: 
$750 per week
Tax: State & Local: 
11.7

Owner will rent June & July weeks of 2026 on a Fri to Fri basis available. 

 

Pool Heated to 81 degrees July & August, included in the rental rate. Pool Heated to 81 June & September,  additional $400 per week propane fee. 

 

 

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Waterfront & View on Edgartown Great Pond, Association Private Beach and Tennis, Central A/C

Waterfront Retreat on Edgartown Great Pond with Private Beach Access & Tennis

MVVR EXCLUSIVE:
Set in a peaceful waterfront location within the desirable Boldwater area, this beautiful contemporary 4-bedroom,...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$3,200 - $8,900
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$3,200
6
7
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12
$3,600
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$3,600
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25
26
$4,200
27
28
29
30
 $5,800
July 2027
SuMoTuWeThFrSaWeek
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2
3
$5,800
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5
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$7,500
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$7,500
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24
$7,500
25
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30
31
$8,900
August 2027
SuMoTuWeThFrSaWeek
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2
3
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$8,900
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$8,900
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$8,900
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$8,900
29
30
31
 $3,700
September 2027
SuMoTuWeThFrSaWeek
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2
3
4
$3,700
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6
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11
$3,250
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$3,250
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25
$3,250
26
27
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29
30
 $3,250
Clean Fee: 
$625 per week
Tax: State & Local: 
11.7

 

 

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Newly update mid-century modern beach house set in the private community of homes surrounding Sengekontacket pond. The cozy summer cottage offers indoor and outdoor living at its best with a...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
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: 
$400 per week
Tax: State & Local: 
11.7
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Modern Summer Home, Newly updated, Perfect Central Location

MVVR Exclusive:  Charming Summer Vacation Home in Dodger's Hole area of Edgartown

Step into the perfect summer retreat with this inviting coastal cottage-style home, designed with an open first-floor layout, highlighted in...Read more

Location: 
Edgartown
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$2,000 - $3,600
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$2,000
6
7
8
9
10
11
12
$2,000
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14
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16
17
18
19
$2,500
20
21
22
23
24
25
26
$2,800
27
28
29
30
 $3,600
July 2027
SuMoTuWeThFrSaWeek
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2
3
$3,600
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5
6
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10
$3,600
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$3,600
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24
$3,600
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30
31
$3,900
August 2027
SuMoTuWeThFrSaWeek
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2
3
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$4,100
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14
$4,100
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$4,100
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$3,500
29
30
31
 $2,700
September 2027
SuMoTuWeThFrSaWeek
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2
3
4
$2,700
5
6
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11
$2,700
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$2,700
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25
$2,700
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28
29
30
 
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7

 

 

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Gorgeous Katama Vacation Home, Heated Pool 20 x 40. 1.2 mi to Beach and Town, Large Landscaped Yard.

This beautifully detailed home offers the perfect retreat for vacationing families, ideally situated just 1.2 miles from both Edgartown Village and South Beach. Convenient bike paths are only a few...Read more

Location: 
Katama
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,000 - $17,000
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$9,800
6
7
8
9
10
11
12
$9,800
13
14
15
16
17
18
19
$11,500
20
21
22
23
24
25
26
$15,000
27
28
29
30
 $15,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$15,500
4
5
6
7
8
9
10
$15,500
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17
$15,500
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19
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24
$15,500
25
26
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30
31
$17,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$17,000
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14
$17,000
15
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$17,000
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$17,000
29
30
31
 $9,000
September 2027
SuMoTuWeThFrSaWeek
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2
3
4
$9,000
5
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$7,500
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$7,500
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25
$7,500
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27
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29
30
 $6,000
Clean Fee: 
$420 per week
Tax: State & Local: 
11.7

Pool Heated to 84 degrees, included in rental rate July & August weeks

Pool Heated 84 degrees, additional $500 June & September

Pool Heated to 84 degrees May and October please inquire!

 

Pet Friendly on a case by case basis

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