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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:
$15,600 - $15,600
June 2027
SuMoTuWeThFrSaWeek
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30
 $15,600
July 2027
SuMoTuWeThFrSaWeek
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2
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$15,600
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$15,600
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$15,600
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$15,600
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$15,600
August 2027
SuMoTuWeThFrSaWeek
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$15,600
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$15,600
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$15,600
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$15,600
29
30
31
 
September 2027
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Clean Fee: 
$875 per rental period
Tax: State & Local: 
11.7
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Herring Creek Summer Retreat, Waterfront, Oversized Pool, Private Association Shore Beach

Nestled into an expansive waterfront lot on the Edgartown Great Pond in prestigious Herring Creek Farm, you’ll find this true Vineyard casual cottage adorned with antique Vineyard collections of original...Read more

Location: 
Katama
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,000 - $15,500
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$8,000
6
7
8
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10
11
12
$8,500
13
14
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18
19
$10,000
20
21
22
23
24
25
26
$10,000
27
28
29
30
 $12,000
July 2027
SuMoTuWeThFrSaWeek
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2
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$12,000
4
5
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$14,000
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$14,000
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19
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21
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$14,000
25
26
27
28
29
30
31
$14,000
August 2027
SuMoTuWeThFrSaWeek
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2
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$15,500
8
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$15,500
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16
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20
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$15,000
22
23
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25
26
27
28
$15,000
29
30
31
 $14,000
September 2027
SuMoTuWeThFrSaWeek
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2
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$14,000
5
6
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$10,000
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13
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$9,000
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$8,000
26
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29
30
 $6,000
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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Exceptional Main & Guest House, 20 x 40 Heated Pool with Stone Patio Surround, Tucked on Large Landscaped Acreage, 2 miles to Beautiful Lambert's Cove Beach, Sleeps 8

This exceptional vacation home and guest house have been recently updated, offering a large, heated saltwater pool nestled on expansive, private acreage in the desirable Indian Hill area of West...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$11,000 - $15,500
June 2027
SuMoTuWeThFrSaWeek
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$11,000
6
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$11,000
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$11,000
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21
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$11,000
27
28
29
30
 $14,500
July 2027
SuMoTuWeThFrSaWeek
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2
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$14,500
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$14,500
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$14,500
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$14,500
25
26
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30
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$14,500
August 2027
SuMoTuWeThFrSaWeek
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$15,500
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$15,500
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$15,500
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$14,500
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30
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 $11,000
September 2027
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
26
27
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29
30
 $11,000
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

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

 

Pool Heated to 82 degrees, June, Sept & October additional $300 propane surcharge per week. 

 

Requests for pool heated above 82 additional cost.  Please inquire with an agent for details. 

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Picture Perfect Newly Updated Edgartown home. Heated Saltwater Pool, Gorgeous Large Yard

Note: Pool is 14 x 30', 3.5 feet to 6 feet deep. Owner offering a 10% discount off the rental rate for the weeks of 7/11, 7/18, 8/23 - 2026,...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$8,500 - $15,500
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
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$13,500
20
21
22
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25
26
$13,500
27
28
29
30
 $13,500
July 2027
SuMoTuWeThFrSaWeek
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2
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$13,500
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$14,000
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$14,000
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$14,000
25
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30
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$14,500
August 2027
SuMoTuWeThFrSaWeek
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$14,500
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$15,500
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$15,500
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$15,500
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30
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 $15,000
September 2027
SuMoTuWeThFrSaWeek
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$15,000
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$14,000
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$13,000
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$13,000
26
27
28
29
30
 
Clean Fee: 
$650 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 propane surcharge 

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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 - $15,220
June 2027
SuMoTuWeThFrSaWeek
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$7,350
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$8,920
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$11,020
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$12,650
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 $13,650
July 2027
SuMoTuWeThFrSaWeek
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$13,650
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$13,650
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$13,650
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$14,700
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$15,220
August 2027
SuMoTuWeThFrSaWeek
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$15,220
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$15,220
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$15,220
22
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$10,500
29
30
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 $8,920
September 2027
SuMoTuWeThFrSaWeek
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$8,920
5
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$7,350
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$7,350
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$7,350
26
27
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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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Owner offering 15% off all remaining weeks open 2026! 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:
$3,800 - $15,170
June 2027
SuMoTuWeThFrSaWeek
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$6,800
6
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$6,800
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$6,800
20
21
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$6,800
27
28
29
30
 $6,800
July 2027
SuMoTuWeThFrSaWeek
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2
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$6,800
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5
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$11,050
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12
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$11,050
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19
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$11,050
25
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$11,050
August 2027
SuMoTuWeThFrSaWeek
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$15,170
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$15,170
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$15,170
22
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$15,170
29
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 $5,950
September 2027
SuMoTuWeThFrSaWeek
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$5,950
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$5,950
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$5,950
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$5,950
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30
 $5,950
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Owners are also open to weekday arrival and departure to accommodate the need for auto ferry ticket reservations. 

 

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Lovely 6 Bedroom Home in Heart of Katama, Multiple Living Spaces, Perfect for Extended Families, 8/10ths mile to South Beach

Note: Recent upgrades include a newly redesigned luxury spa-style primary bath, and an additional powder room on the first level for enhanced guest convenience. Also, a new additional powder room has been added...Read more

Location: 
Katama
Sleeps: 
11
Bedrooms: 
6
Baths: 
3
Price Range:
$5,000 - $15,000
June 2027
SuMoTuWeThFrSaWeek
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2
3
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5
$6,500
6
7
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12
$6,500
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$7,000
20
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$8,500
27
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29
30
 $13,000
July 2027
SuMoTuWeThFrSaWeek
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2
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$13,000
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$14,500
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$14,500
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$15,000
25
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$15,000
August 2027
SuMoTuWeThFrSaWeek
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$15,000
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$15,000
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$15,000
22
23
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25
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27
28
$14,500
29
30
31
 $11,500
September 2027
SuMoTuWeThFrSaWeek
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2
3
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$11,500
5
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$8,000
12
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$8,000
19
20
21
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25
$8,000
26
27
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29
30
 $8,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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Spacious Contemporary Home, New Heated 20 x40 Pool, Beautifully Landscaped. Desirable Deep Bottom Community of Homes, Association Tennis Courts, Shared Dock on Great Pond for Launching Kayaks

Tucked in the exquisite community of homes known as Deep Bottom, this spacious home is sited on 2.78 acres with gorgeous views across horse pasture, pond, and meadows. Adding to the serenity of...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
5
Baths: 
3
Price Range:
$13,000 - $15,000
June 2027
SuMoTuWeThFrSaWeek
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$13,000
27
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30
 $13,000
July 2027
SuMoTuWeThFrSaWeek
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2
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$13,000
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$13,000
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$13,000
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$13,000
25
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$13,000
August 2027
SuMoTuWeThFrSaWeek
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$15,000
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$15,000
15
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$15,000
22
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$15,000
29
30
31
 
September 2027
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Spa on the property is not available for renter use. 

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Stylish Main & Guest House with Heated Pool, 10 x 16 Plunge Pool,Landscaped Yard, Walk to Village Center, Sleeps 8-10 2026- Owner will rent Main House Only in June for $10,000 per week, and $15,000 open July weeks.Inquire for Details!

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:
$15,000 - $15,000
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: 
$700 per week
Tax: State & Local: 
11.7

Owner will rent main house only for $14,000 per week plus fees. There would be no one in the guest house during renter stay!  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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Outstanding In-town Home, Gorgeous Professionally Landscaped Yard, 5 Min walk to Main Street Shops & Restaurants

Located on a quiet street in the Edgartown Village area, this lovely 5 bedroom, 3 bath Home has been all newly updated. The home is bordered by lush lawn, privacy fencing...Read more

Location: 
Edgartown
Sleeps: 
9
Bedrooms: 
5
Baths: 
3
Price Range:
$7,000 - $15,000
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$8,000
6
7
8
9
10
11
12
$8,000
13
14
15
16
17
18
19
$9,000
20
21
22
23
24
25
26
$9,000
27
28
29
30
 $12,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$12,500
4
5
6
7
8
9
10
$10,500
11
12
13
14
15
16
17
$11,000
18
19
20
21
22
23
24
$11,000
25
26
27
28
29
30
31
$12,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$13,000
8
9
10
11
12
13
14
$13,000
15
16
17
18
19
20
21
$15,000
22
23
24
25
26
27
28
$12,000
29
30
31
 $12,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$12,000
5
6
7
8
9
10
11
$8,000
12
13
14
15
16
17
18
$8,000
19
20
21
22
23
24
25
$8,000
26
27
28
29
30
 $8,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Owner reduced rates for available weeks June, July & August - see calendar for adjusted rates

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Gorgeous, Classic, Spacious New England Home, Main & Carriage House, In the Heart of the Katama Area of Edgartown, Multiple Living Spaces both Inside & Out, Sleeps 10. Private Landscaped Grounds. Multiple Decks, Screened Porch

Experience the essence of modern living in an exquisite New England home boasting classic design, nestled on meticulously landscaped grounds just moments away from South Beach and Edgartown Village.

The Main...Read more

Location: 
Katama
Sleeps: 
10
Bedrooms: 
5
Baths: 
4
Price Range:
$10,000 - $15,000
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: 
$1250 per week
Tax: State & Local: 
11.7
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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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13
14
15
16
17
18
19
20
21
22
23
24
25
26
$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
1
2
3
4
5
6
7
$15,000
8
9
10
11
12
13
14
$15,000
15
16
17
18
19
20
21
$15,000
22
23
24
25
26
27
28
$11,000
29
30
31
 $8,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,000
5
6
7
8
9
10
11
$8,000
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
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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Gorgeous Custom Contemporary Farmhouse Design, Heated Pool & Spa, Located Just on the Outskirts of Edgartown Center! 4 Bedrooms, 4.5 Baths

Heated Pool and Outdoor Living

Enjoy a beautifully designed 30x16' heated pool with a depth ranging from 3.7 feet at the shallow end to 7 feet at the deep end....Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$7,500 - $14,800
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,600
6
7
8
9
10
11
12
$7,600
13
14
15
16
17
18
19
$7,600
20
21
22
23
24
25
26
$10,600
27
28
29
30
 $12,900
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$12,900
4
5
6
7
8
9
10
$12,900
11
12
13
14
15
16
17
$12,900
18
19
20
21
22
23
24
$12,900
25
26
27
28
29
30
31
$13,650
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$14,700
8
9
10
11
12
13
14
$14,800
15
16
17
18
19
20
21
$14,700
22
23
24
25
26
27
28
$13,600
29
30
31
 $10,600
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$10,600
5
6
7
8
9
10
11
$7,600
12
13
14
15
16
17
18
$7,600
19
20
21
22
23
24
25
$7,600
26
27
28
29
30
 $7,600
Clean Fee: 
$575
Tax: State & Local: 
11.7

Pool heated to 80 included in the rental rate last week in June through the last week in August. Spa is heated to the same temperature as pool. 

Per a renter request the spa can be heated to 101, 4 hours per day 6 to 10 pm for an additional $200 per week.

 

June & September weeks pool heated to 80 additional $250 propane surcharge week, request for higher temperatures, speak with an agent. Spa is heated to the same temperature as the Pool.  Requests for Spa heated to 101 4 hours per day additional $200 per week. 

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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
13
14
15
16
17
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
14
15
16
17
$14,750
18
19
20
21
22
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
16
17
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

 

Special Offers from Owner:

June 13 - 20 - price reduced to $12,000

 

August 22nd - 9/5  2 Week stay for $28,000 instead of $29,500

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Mini Retreat with Pool, Private Peaceful Chilmark Location, Lucy Vincent and Menemsha Beaches Nearby.

Impeccably maintained and updated, this adorable summer home is perfect for families looking for luxury features such as quality linens in a quiet location. The 12 by 18-foot spa pool is...Read more

Location: 
Chilmark
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,800 - $14,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,350
6
7
8
9
10
11
12
$7,350
13
14
15
16
17
18
19
$8,000
20
21
22
23
24
25
26
$12,400
27
28
29
30
 $14,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$14,500
4
5
6
7
8
9
10
$14,500
11
12
13
14
15
16
17
$14,500
18
19
20
21
22
23
24
$14,500
25
26
27
28
29
30
31
$14,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$14,500
8
9
10
11
12
13
14
$14,500
15
16
17
18
19
20
21
$14,500
22
23
24
25
26
27
28
$14,500
29
30
31
 $8,300
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,300
5
6
7
8
9
10
11
$7,650
12
13
14
15
16
17
18
$7,650
19
20
21
22
23
24
25
$7,650
26
27
28
29
30
 $4,800
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

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

Pool heated to 82 degrees, May, June Sept and October additional $150 per week propane surcharge

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