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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
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$13,000
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 $13,000
July 2027
SuMoTuWeThFrSaWeek
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$13,000
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$13,000
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$13,000
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$13,000
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$13,000
August 2027
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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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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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Waterview, Walk to the Beach and Town Center, Impeccably Maintained 4 bedroom Home set in the Heart of Oak Bluffs.

This restored historic J.A. Norton Main and Guest Suite Quarters seamlessly blends 1870s character with the modern comforts today’s travelers appreciate. Nestled in a peaceful  Oak Bluffs neighborhood, the property is just...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$5,500 - $15,000
June 2027
SuMoTuWeThFrSaWeek
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$7,000
6
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$7,000
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$7,000
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$7,000
27
28
29
30
 $7,000
July 2027
SuMoTuWeThFrSaWeek
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2
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$7,000
4
5
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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
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$15,000
22
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$15,000
29
30
31
 $10,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$10,500
5
6
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$6,500
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$5,500
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$5,500
26
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29
30
 $5,500
Clean Fee: 
$400 per week
Tax: State & Local: 
14.45
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Heated Pool, 10 x 16. Edgartown Village Center, Walk to Town, Sleeps 6, South and State Beaches 10 to 12 minute drive.

Beautiful new in-town home with heated pool,screened porch, a lovely, landscaped yard with expansive lawn area and nicely tucked on a quiet street just a 10-minute walk from the Edgartown...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
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
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
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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Beautiful Newly Updated Oak Bluffs Home, Nestled on a Large Landscaped Lot in a Quiet Enclave of Homes. 4 Bedrooms. 4.5 Baths

Step inside to discover a welcoming interior, highlighted by a sunroom featuring comfortable seating around the TV. The open first-floor plan seamlessly integrates the main family room complete with a media...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,000 - $15,000
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
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$6,000
6
7
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10
11
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$6,500
13
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16
17
18
19
$7,500
20
21
22
23
24
25
26
$7,500
27
28
29
30
 $8,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$8,500
4
5
6
7
8
9
10
$8,500
11
12
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15
16
17
$8,500
18
19
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21
22
23
24
$9,000
25
26
27
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29
30
31
$10,000
August 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
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$15,000
8
9
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$16,000
15
16
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$16,000
22
23
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$10,000
29
30
31
 $7,000
September 2027
SuMoTuWeThFrSaWeek
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$7,000
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$6,000
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$6,000
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$6,000
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30
 $6,000
Clean Fee: 
$600 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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6
7
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9
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$12,000
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 $15,000
July 2027
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 2027
SuMoTuWeThFrSaWeek
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$15,000
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$15,000
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$15,000
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$11,000
29
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 $8,000
September 2027
SuMoTuWeThFrSaWeek
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$8,000
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$8,000
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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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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
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2
3
4
5
$14,750
6
7
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$14,750
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$14,750
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$14,750
27
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 $14,750
July 2027
SuMoTuWeThFrSaWeek
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2
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$14,750
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$14,750
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$14,750
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$14,750
25
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$14,750
August 2027
SuMoTuWeThFrSaWeek
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2
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$14,750
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$14,750
15
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$14,750
22
23
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$14,750
29
30
31
 $14,750
September 2027
SuMoTuWeThFrSaWeek
 1
2
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$14,750
5
6
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$14,750
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13
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$14,750
19
20
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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

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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 - $14,700
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
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2
3
$12,900
4
5
6
7
8
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10
$12,900
11
12
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$12,900
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19
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24
$12,900
25
26
27
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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
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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
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10
11
$7,600
12
13
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$7,600
19
20
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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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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 - $14,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,500
6
7
8
9
10
11
12
$6,500
13
14
15
16
17
18
19
$7,000
20
21
22
23
24
25
26
$8,500
27
28
29
30
 $13,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$13,000
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
$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
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18
19
20
21
$15,000
22
23
24
25
26
27
28
$14,500
29
30
31
 $11,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,500
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
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Spacious Colonial with Contemporary Detailing in Fresh Pond Estates, Multiple Living Spaces, Screened Porch, Spacious Deck, AC, Wifi, Beautifully Furnished, Bike Paths at the head of the Road

Spacious, 4 bedroom 3.5 bath contemporary home set in a quiet lovely community on the outskirts of Oak Bluffs. . The main living level features an open concept and hosts a family...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,700 - $14,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,900
6
7
8
9
10
11
12
$5,900
13
14
15
16
17
18
19
$5,900
20
21
22
23
24
25
26
$5,900
27
28
29
30
 $6,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$6,500
4
5
6
7
8
9
10
$6,500
11
12
13
14
15
16
17
$6,500
18
19
20
21
22
23
24
$7,000
25
26
27
28
29
30
31
$7,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$14,500
8
9
10
11
12
13
14
$15,500
15
16
17
18
19
20
21
$15,500
22
23
24
25
26
27
28
$9,000
29
30
31
 $8,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,000
5
6
7
8
9
10
11
$6,900
12
13
14
15
16
17
18
$6,500
19
20
21
22
23
24
25
$6,000
26
27
28
29
30
 $5,700
Clean Fee: 
$550 per week ($375 for interim cleaning on multiple week rentals)
Tax: State & Local: 
14.45
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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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Gracious Village Area 5 Bedroom Home, Light Filled Interior, Mulitple Living Spaces, Large Landscaped Yard, Located on Quiet Side St, 5 min Walk to Main St.

Stunning Edgartown Village Home! This meticulously maintained and newly updated property offers multiple living areas, 5 bedrooms, and 3.5 baths, surrounded by a lushly landscaped yard. Just a 5-minute walk...Read more

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

 

Parking for 3 cars, no on street parking

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Newly Updated Contemporary Home, Heated Pool, Bluestone Patio, Spacious Deck, Tucked Away and Close to Long Point Beach.

Nestled in the town of West Tisbury, this exquisite contemporary residence boasts a heated pool, surrounded by a patio, and enveloped by lush landscaping, offering a private oasis for those seeking...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$7,000 - $14,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,500
6
7
8
9
10
11
12
$8,500
13
14
15
16
17
18
19
$8,500
20
21
22
23
24
25
26
$9,500
27
28
29
30
 $9,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,500
4
5
6
7
8
9
10
$12,000
11
12
13
14
15
16
17
$12,000
18
19
20
21
22
23
24
$12,000
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
$14,000
15
16
17
18
19
20
21
$14,000
22
23
24
25
26
27
28
$14,000
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

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

Pool Heated to 81 in June & Sept additional $250 per week

Pool size is 20 x 40 

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Summer Wind in the Heart of Oak Bluffs, Water views. 2 minute Walk to Inkwell Beach & 5 minute walk to town, All Newly Remodeled 5 Bedroom, 3 Bath Home With Deluxe Amenities

Set in the heart of Oak Bluffs center, this newly renovated home features water views, walk to Inkwell Beach and Pay Beach and walk to the town center all within...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$7,000 - $14,000
June 2027
SuMoTuWeThFrSaWeek
 1
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
$10,000
27
28
29
30
 $12,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$12,000
4
5
6
7
8
9
10
$13,000
11
12
13
14
15
16
17
$14,000
18
19
20
21
22
23
24
$14,000
25
26
27
28
29
30
31
$15,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$22,000
8
9
10
11
12
13
14
$22,000
15
16
17
18
19
20
21
$22,000
22
23
24
25
26
27
28
$14,000
29
30
31
 $9,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,500
5
6
7
8
9
10
11
$8,000
12
13
14
15
16
17
18
$8,500
19
20
21
22
23
24
25
$8,500
26
27
28
29
30
 $7,000
Clean Fee: 
$550
Tax: State & Local: 
14.45
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Edgartown, Katama Area, Spacious Luxury with Designer Detailing, Chef's Kitchen, Multiple Living Spaces, 4 Bedrooms, 3.5 Baths

New in 2022 large addition and full renovation to this beautiful Katama home. Located within walking distance of town (1.4 miles) and biking to Katama South Beach (2.1 miles). 

The...Read more

Location: 
Katama
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$14,000 - $14,000
June 2027
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 2027
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
31
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
$14,000
15
16
17
18
19
20
21
$14,000
22
23
24
25
26
27
28
29
30
31
 
September 2027
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
 
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

No Rooms tax,  Owner is Tax Exempt for weeks 8/8 & 8/15

 

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Luxurious Home, Privately Situated in the West Chop Area of Vineyard Haven, Heated Pool, Spa, North Shore Waterviews, Multiple Indoor/Outdoor LIving Spaces. 6 Bedrooms, 5.5 Baths Sleeps 13.

Exceptional Luxury Rental: Elegant 6-Bedroom Estate in West Chop, Vineyard Haven

Experience refined summer living in this stunning six-bedroom, five-and-a-half-bath coastal retreat, ideally located in the prestigious West Chop area...Read more

Location: 
Vineyard Haven
Sleeps: 
13
Bedrooms: 
6
Baths: 
5
Price Range:
$14,000 - $14,000
June 2027
SuMoTuWeThFrSaWeek
 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
 $25,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$25,000
4
5
6
7
8
9
10
$25,000
11
12
13
14
15
16
17
$30,000
18
19
20
21
22
23
24
$30,000
25
26
27
28
29
30
31
$35,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$35,000
8
9
10
11
12
13
14
$35,000
15
16
17
18
19
20
21
$35,000
22
23
24
25
26
27
28
$35,000
29
30
31
 $25,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$25,000
5
6
7
8
9
10
11
$18,000
12
13
14
15
16
17
18
$18,000
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$2000 per week
Tax: State & Local: 
11.7

 

 

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