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Luxury Gambrel Home. Heated Pool, Bluestone Patio Surround, Patio Dining, Walk to Town, 4 Bedrooms, 3.5 Baths

Unwind with family and friends in this newly constructed vacation home, featuring a heated pool and ideally situated on a peaceful lane, just a short stroll to the village center....Read more

Location: 
Edgartown
Sleeps: 
10
Bedrooms: 
4
Baths: 
3
Price Range:
$11,500 - $22,500
June 2025
SuMoTuWeThFrSa
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July 2025
SuMoTuWeThFrSaWeek
 1
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$22,500
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$22,500
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$22,500
27
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31
 $24,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$24,500
3
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$24,500
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$24,500
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$24,500
24
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28
29
30
$24,500
31
 $15,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
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5
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$15,500
7
8
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10
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$13,500
14
15
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19
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$13,500
21
22
23
24
25
26
27
$13,500
28
29
30
 $11,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Ferry Tickets Available for weeks 8/30-9/6 - please inquire

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HERGT

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Property Details
Luxury Retreat Chilmark, Key to Quansoo Private Association Beach, Heated Pool, Stone Patio, Pool Pavillion, Propane Fire Pit, Set on 7.5 private acres

New for 2024: Heated Pool with Patio Surround, Propane Fire Pit,  Post and Beam Pool Pavillion with outdoor kitchen hosting 36" Lynx Grill,  Lynx Sink, Power Burner, undercounter Fridge and dishwasher, Raised...Read more

Location: 
Chilmark
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$15,000 - $15,000
June 2025
SuMoTuWeThFrSa
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July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
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$20,500
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$22,500
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$22,500
27
28
29
30
31
 $25,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$25,000
3
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$25,000
10
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$25,000
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18
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22
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$25,000
24
25
26
27
28
29
30
$15,000
31
 $15,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
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5
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$15,000
7
8
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$15,000
14
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19
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$15,000
21
22
23
24
25
26
27
$15,000
28
29
30
 $15,000
Clean Fee: 
$850 per week
Tax: State & Local: 
11.7

Transferrable ferry ticket available 8/23-8/30.  Please inquire for details! (mv)

 

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

 

Pool Heated to 82 degrees June & Sept weeks $300/week 

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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:
$0 - $0
June 2025
SuMoTuWeThFrSa
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29
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July 2025
SuMoTuWeThFrSaWeek
 1
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$35,000
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$35,000
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25
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$35,000
27
28
29
30
31
 $35,000
August 2025
SuMoTuWeThFrSaWeek
 1
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$35,000
3
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$35,000
10
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$35,000
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$35,000
24
25
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27
28
29
30
$35,000
31
 $30,000
September 2025
SuMoTuWeThFrSaWeek
 1
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$30,000
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21
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25
26
27
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29
30
 
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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RANSW

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Property Details
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:
$22,000 - $57,000
June 2025
SuMoTuWeThFrSa
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29
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July 2025
SuMoTuWeThFrSaWeek
 1
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$57,000
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$57,000
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$57,000
27
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31
 $57,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$57,000
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$57,000
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$57,000
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$57,000
24
25
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27
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29
30
$57,000
31
 $57,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
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5
6
$57,000
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$38,000
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$38,000
21
22
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27
$38,000
28
29
30
 $22,000
Clean Fee: 
$1000 per week
Tax: State & Local: 
11.7

Owner offering a 10% discount on available weeks

 

 

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CALWM

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Property Details
Exquisite New Luxurious Home, Tucked in the Private Enclave, Known as -The Preserve, Heated Saltwater Pool 18' x 45, Screened Porch, Propane Fire pit with Adirondack Seating, Designer Interior

"The Preserve" in Oak Bluffs is a desirable enclave of homes that offers a serene and alluring living environment. This expansive luxury home designed by noted architect Chuck Sullivan was completed...Read more

Location: 
Oak Bluffs
Sleeps: 
12
Bedrooms: 
6
Baths: 
5
Price Range:
$17,000 - $32,500
June 2025
SuMoTuWeThFrSa
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July 2025
SuMoTuWeThFrSaWeek
 1
2
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$27,000
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$27,000
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$27,000
27
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30
31
 $28,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$28,500
3
4
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$30,000
10
11
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$32,500
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18
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22
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$32,500
24
25
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27
28
29
30
$27,000
31
 $20,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$20,000
7
8
9
10
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13
$17,500
14
15
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19
20
$17,500
21
22
23
24
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26
27
$17,500
28
29
30
 
Clean Fee: 
$960 per week
Tax: State & Local: 
11.7

Pool Heated to 82 degrees  July & August  weeks, included in the rental rate

Pool Heated to 82 degrees June & September weeks, additional $300 per week surcharge

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NAIDN

(0)Inquire/Share
Property Details
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:
$10,000 - $14,000
June 2025
SuMoTuWeThFrSa
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29
30
 
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$27,000
13
14
15
16
17
18
19
$30,000
20
21
22
23
24
25
26
$30,000
27
28
29
30
31
 $35,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$35,000
3
4
5
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7
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$35,000
10
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$35,000
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18
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$35,000
24
25
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29
30
$32,000
31
 $18,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$18,000
7
8
9
10
11
12
13
$14,000
14
15
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18
19
20
$14,000
21
22
23
24
25
26
27
$14,000
28
29
30
 $10,000
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

Pool Heated to 81 degrees July & August, included in the rental rate

Pool Heated to 81 June, additional $400 per week propane fee. 

Pool is not heated in September 2025 from 9/13 on. 

 

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MOR12

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Property Details
Distinctive Luxury Retreat Edgartown, Heated Saltwater Pool, 36 x 19', Pickle Ball Court, Sleeps 10

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: 
10
Bedrooms: 
5
Baths: 
4
Price Range:
$20,000 - $25,000
June 2025
SuMoTuWeThFrSa
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29
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July 2025
SuMoTuWeThFrSaWeek
 1
2
3
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5
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7
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10
11
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$25,000
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14
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18
19
$25,000
20
21
22
23
24
25
26
$32,000
27
28
29
30
31
 $32,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$32,000
3
4
5
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7
8
9
$32,000
10
11
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$32,000
17
18
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21
22
23
$29,500
24
25
26
27
28
29
30
$27,500
31
 $20,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$20,000
7
8
9
10
11
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13
$20,000
14
15
16
17
18
19
20
$20,000
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$1200 per week
Tax: State & Local: 
11.7

Rates just reduced for available weeks in July - see calendar for adjusted rates

 

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 $250 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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CHOAY

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Property Details
Gorgeous Luxury Home, Edgartown, Heated Pool, Pickle Ball Court, Multiple Living Spaces, 4 Bedrooms. 4.5 Baths Sleeps 9.

This stunning contemporary vacation home in Edgartown offers an exceptional blend of indoor and outdoor living spaces, making it an ideal retreat for relaxation and entertainment. The beautifully landscaped yard features...Read more

Location: 
Edgartown
Sleeps: 
9
Bedrooms: 
4
Baths: 
4
Price Range:
$12,000 - $15,000
June 2025
SuMoTuWeThFrSa
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29
30
 
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$15,000
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14
15
16
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18
19
$15,000
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21
22
23
24
25
26
$15,000
27
28
29
30
31
 $18,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$18,000
3
4
5
6
7
8
9
$23,000
10
11
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$22,000
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18
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21
22
23
$23,000
24
25
26
27
28
29
30
$15,000
31
 $12,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$12,000
7
8
9
10
11
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13
$12,000
14
15
16
17
18
19
20
$12,000
21
22
23
24
25
26
27
$12,000
28
29
30
 $12,000
Clean Fee: 
$1000 per week
Tax: State & Local: 
11.7

Transferrable ferry tickets available 8/24-8/31. Please inquire for details! (mv)

 

Rates just reduced for available weeks in July & August - see calendar for adjusted rates

 

Pool Heat additional $250 per week June & September

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CAS65

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Property Details
Sophisticated, Contemporary Vacation Retreat, Main & Guest House, Heated Pool, Outdoor Living Area, Pond Access for Paddle Boarding and Kayaking, Private Location

A light-filled, coastal-inspired luxury vacation home and guest house tucked in a private location featuring views of Watcha Pond, multiple living spaces, a gourmet kitchen, 4 bedrooms, 4 luxury bathrooms, and the ability to...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$15,000 - $26,000
June 2025
SuMoTuWeThFrSa
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July 2025
SuMoTuWeThFrSaWeek
 1
2
3
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5
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7
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12
$26,000
13
14
15
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18
19
$26,000
20
21
22
23
24
25
26
$26,000
27
28
29
30
31
 $26,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$26,000
3
4
5
6
7
8
9
$26,000
10
11
12
13
14
15
16
$18,000
17
18
19
20
21
22
23
$18,000
24
25
26
27
28
29
30
$26,000
31
 $19,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$19,000
7
8
9
10
11
12
13
$19,000
14
15
16
17
18
19
20
$19,000
21
22
23
24
25
26
27
$19,000
28
29
30
 
Clean Fee: 
$850 per week
Tax: State & Local: 
11.7

Ferry Tickets Availabe 8/9 - 8/16 and 8/16 - 8/23.  (mv) Inquire for details! 

RATE REDUCED FOR WEEKS 8/9-8/23 - see calendar for adjusted rates

 

Pool heated to 81 degrees included in rental rate July to 8/26.  Pool heated to 81 degrees June & September weeks additional $300 propane surcharge weekly.  

 

Main House only may be rented the weeks of  5/24 to 6/20, and 9/2 to 9/30 for $2000 less than the posted rate for Main and Guest House. Inquire for further details!

 

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JOSEJ

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Property Details
Exquisite Coastal Style Home, Pool, Patio, Landscaped Yard! 10 minute walk to Oak Bluffs Center, Luxury Interior, 3 bedrooms, 4 baths, Multiple Living Spaces

This newly constructed, luxurious home offers the perfect blend of comfort, style, and convenience. Featuring a heated 16 x 32' pool with varying depths of 3 to 8 feet, a...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,500 - $6,500
June 2025
SuMoTuWeThFrSa
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2
3
4
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9
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29
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July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$8,500
13
14
15
16
17
18
19
$10,000
20
21
22
23
24
25
26
$8,500
27
28
29
30
31
 $13,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$13,500
3
4
5
6
7
8
9
$13,500
10
11
12
13
14
15
16
$13,500
17
18
19
20
21
22
23
$13,500
24
25
26
27
28
29
30
$9,350
31
 $7,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,000
7
8
9
10
11
12
13
$6,500
14
15
16
17
18
19
20
$6,500
21
22
23
24
25
26
27
$6,500
28
29
30
 
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

Rates just reduced for available weeks in July & August by 15% - see calendar for adjusted rates

 

Pool Heated to  81 degrees included in rental rate last Sat in June to first Sat in September. Pool Depth 3 feet to 8 Feet 

Pool Heated to 81 degrees June and September weeks additional $275 per week  

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BROWA

(0)Inquire/Share
Property Details
Stylish Main & Guest House with Heated Pool, 10 x 16 Plunge Pool,Landscaped Yard, Walk to Village Center, Sleeps 8-10

This inviting 5-bedroom, 3.5-bath compound is perfect for extended families and friends. It features a Main House and separate Guest House, both offering a heated plunge pool, 10 x 16...Read more

Location: 
Edgartown
Sleeps: 
9
Bedrooms: 
5
Baths: 
3
Price Range:
$10,000 - $20,000
June 2025
SuMoTuWeThFrSa
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2
3
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12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$12,000
13
14
15
16
17
18
19
$19,000
20
21
22
23
24
25
26
$19,000
27
28
29
30
31
 $20,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$20,000
3
4
5
6
7
8
9
$20,000
10
11
12
13
14
15
16
$20,000
17
18
19
20
21
22
23
$20,000
24
25
26
27
28
29
30
$17,000
31
 $12,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$12,000
7
8
9
10
11
12
13
$12,000
14
15
16
17
18
19
20
$12,000
21
22
23
24
25
26
27
$12,000
28
29
30
 $12,000
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

Ferry Tickets available 8/23-8/30 (mv)- please inquire for details!

 

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

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

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SHAN2

(0)Inquire/Share
Property Details
Newly Updated Vacation Home, Katama Area of Edgartown, 12 x 30' Heated Pool, 4 Bedrooms, 4.5 Baths, Separate Recreation Barn with Ping Pong Table, Large Screen TV and Game Area, Bike Path to Village Center and to South Beach

Outstanding, modern farmhouse design, with heated pool and additional entertainment barn with ping-pong table, game table, game board games, and large screened TV just a few steps across the yard....Read more

Location: 
Katama
Sleeps: 
12
Bedrooms: 
4
Baths: 
4
Price Range:
$7,350 - $8,920
June 2025
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$13,650
13
14
15
16
17
18
19
$13,650
20
21
22
23
24
25
26
$14,700
27
28
29
30
31
 $15,220
August 2025
SuMoTuWeThFrSaWeek
 1
2
$15,220
3
4
5
6
7
8
9
$15,220
10
11
12
13
14
15
16
$15,220
17
18
19
20
21
22
23
$15,220
24
25
26
27
28
29
30
$10,500
31
 $8,920
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$8,920
7
8
9
10
11
12
13
$7,580
14
15
16
17
18
19
20
$7,350
21
22
23
24
25
26
27
$7,350
28
29
30
 $7,350
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Pool Heated to 80 degrees July & August included in rental rates. 

Pool heat is an additional $250 May, June, September, October

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MALFC

(0)Inquire/Share
Property Details
Stunning Luxury Home, Sought after Field Club Location, 18 x 32" Heated Gunite Pool, Main and Guest Carriage House

Luxurious Custom Crafted Home in the heart of the Katama area of Edgartown. This beautiful home offers discerning vacationers multiple indoor and outdoor living spaces, which include an 18 x...Read more

Location: 
Katama
Sleeps: 
9
Bedrooms: 
5
Baths: 
4
Price Range:
$15,000 - $25,000
June 2025
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$40,000
13
14
15
16
17
18
19
$20,000
20
21
22
23
24
25
26
$40,000
27
28
29
30
31
 $25,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$25,000
3
4
5
6
7
8
9
$40,000
10
11
12
13
14
15
16
$40,000
17
18
19
20
21
22
23
$40,000
24
25
26
27
28
29
30
$40,000
31
 $30,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$30,000
7
8
9
10
11
12
13
$25,000
14
15
16
17
18
19
20
$15,000
21
22
23
24
25
26
27
$15,000
28
29
30
 $15,000
Clean Fee: 
$1250 per week
Tax: State & Local: 
11.7

Owner reduced rates for available weeks in June and July - see calendars for adjusted rates

 

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

Pool Heated to 81 June & September weeks, additional $250 per week

Pool Heated to 81 May& October weeks, additional $300 per week

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TAVAM

(0)Inquire/Share
Property Details
Outstanding, Newly Updated Vacation Retreat, Heated Saltwater Pool. Multiple Living Spaces, All New Kitchen, Gorgeous Yard, Set in Quiet, Lovely Commmunity of Homes, Stonegate

Impeccable Vacation Getaway with Updated Amenities and a Heated Saltwater Pool

Nestled within the serene community of Stonegate, this exceptional retreat offers a rejuvenating escape. Conveniently located just a brief...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$7,000 - $16,000
June 2025
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$13,000
13
14
15
16
17
18
19
$13,000
20
21
22
23
24
25
26
$13,000
27
28
29
30
31
 $16,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$16,000
3
4
5
6
7
8
9
$16,000
10
11
12
13
14
15
16
$16,000
17
18
19
20
21
22
23
$16,000
24
25
26
27
28
29
30
$13,800
31
 $11,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$11,000
7
8
9
10
11
12
13
$11,000
14
15
16
17
18
19
20
$9,000
21
22
23
24
25
26
27
$9,000
28
29
30
 $9,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Pool heated to 82 July & August included in rental rate.  

Spa area in the pool is heated to the same temperature as the pool and is not available Spa jets are also not available for renter use. 

 

Pool heated to 82 June & September when weeks are available additional $300 per week propane surcharge.

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BELLJ

(0)Inquire/Share
Property Details
Gorgeous Beach Retreat, 20 x 40 Heated Pebble Tec Pool, Tennis Courts, Walk or Bike to South Beach

Ferry Tickets available 7/13-7/20  & 7/20 to 7/27.  Inquire for details! (mv)

This stunning newly updated contemporary beach home is just steps from South Beach, and even fewer steps to the bike...Read more

Location: 
Katama
Sleeps: 
10
Bedrooms: 
4
Baths: 
3
Price Range:
$10,000 - $30,000
June 2025
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$25,000
13
14
15
16
17
18
19
$25,000
20
21
22
23
24
25
26
$25,000
27
28
29
30
31
 $30,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$30,000
3
4
5
6
7
8
9
$30,000
10
11
12
13
14
15
16
$30,000
17
18
19
20
21
22
23
$30,020
24
25
26
27
28
29
30
$25,000
31
 $20,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$20,000
7
8
9
10
11
12
13
$11,000
14
15
16
17
18
19
20
$11,000
21
22
23
24
25
26
27
$11,000
28
29
30
 $11,000
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

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

Pool heated to 82 additional $300 per week June & September, May & October pool heated to 82 additional $400 per week

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