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Tucked in the Heart of the Katama area of Edgartown, Charming, Spacious, Open Floor Plan Garage Apartment

Perfect Summer Getaway in Katama

Enjoy your summer escape in this spacious and immaculate apartment, ideally located in the heart of Katama—just one mile from South Beach and two miles...Read more

Location: 
Edgartown
Sleeps: 
2
Bedrooms: 
1
Baths: 
1
Price Range:
$1,700 - $3,000
June 2025
SuMoTuWeThFrSaWeek
1
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10
11
12
13
14
15
16
17
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26
27
28
29
30
 $2,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,500
6
7
8
9
10
11
12
$2,500
13
14
15
16
17
18
19
$2,500
20
21
22
23
24
25
26
$2,500
27
28
29
30
31
 $2,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$2,500
3
4
5
6
7
8
9
$3,000
10
11
12
13
14
15
16
$3,000
17
18
19
20
21
22
23
$2,800
24
25
26
27
28
29
30
$2,500
31
 $1,700
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$1,700
7
8
9
10
11
12
13
$1,700
14
15
16
17
18
19
20
$1,700
21
22
23
24
25
26
27
$1,700
28
29
30
 
Clean Fee: 
$180 per week
Tax: State & Local: 
11.7
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South Beach Edgartown, WiFi, Central A/C

This 3 bedroom, 2 bath immaculate Katama Cape is conveniently located 2 miles to the beach and 1.5 miles to Edgartown Center.  Comfortable, bright interior and great yard and deck...Read more

Location: 
Katama
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2025
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
 $3,600
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,600
6
7
8
9
10
11
12
$3,600
13
14
15
16
17
18
19
$3,600
20
21
22
23
24
25
26
$3,600
27
28
29
30
31
 $3,600
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,600
3
4
5
6
7
8
9
$3,600
10
11
12
13
14
15
16
$3,600
17
18
19
20
21
22
23
$3,600
24
25
26
27
28
29
30
$3,000
31
 $2,600
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,600
7
8
9
10
11
12
13
$2,000
14
15
16
17
18
19
20
$2,000
21
22
23
24
25
26
27
$1,800
28
29
30
 $1,800
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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Ocean View House! Luxury Main & Guest, Waterfront on the Vineyard Sound, Association Beach, 5 Bedrooms, 3 Baths

Stunning Spring Point Vacation Retreat! This newly renovated Main & Guest House is situated in a 335 acre parcel of Chilmark with approximately 40 homes scattered throughout the acreage, and is...Read more

Location: 
Chilmark
Sleeps: 
8
Bedrooms: 
5
Baths: 
3
Price Range:
$15,000 - $30,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
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12
13
14
15
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17
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20
21
22
23
24
25
26
27
28
29
30
 $40,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$40,000
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
 $25,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$25,000
3
4
5
6
7
8
9
$25,000
10
11
12
13
14
15
16
$25,000
17
18
19
20
21
22
23
$25,000
24
25
26
27
28
29
30
$25,000
31
 $17,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$17,000
7
8
9
10
11
12
13
$17,000
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: 
$750 per week
Tax: State & Local: 
11.7
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Lovely Updated Cape Style Home, Beautifully Landscaped Yard, Deck & Patio with Multiple Seating Areas & Outdoor Dining

Nestled in a peaceful lane in Edgartown's desirable Dodger’s Hole Area, this charming Cape-style home offers a central location with easy access to Edgartown, Oak Bluffs, Vineyard Haven, and several...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,500 - $6,500
June 2025
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
 $3,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
6
7
8
9
10
11
12
$4,500
13
14
15
16
17
18
19
$3,500
20
21
22
23
24
25
26
$3,500
27
28
29
30
31
 $4,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,000
3
4
5
6
7
8
9
$6,500
10
11
12
13
14
15
16
$6,500
17
18
19
20
21
22
23
$6,500
24
25
26
27
28
29
30
$4,500
31
 $4,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,500
7
8
9
10
11
12
13
$3,500
14
15
16
17
18
19
20
$3,000
21
22
23
24
25
26
27
$3,000
28
29
30
 $2,500
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Owner reduced rates for available weeks in July - see calendar for adjusted rates

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Katama South Beach, 20 x 40 Heated Gunite Pool, Walk or Bike to the Beach, Luxury Home,

Stunning tri-level vacation home bordered by professionally landscaped grounds with Gunite pool, located in a quiet Katama neighborhood, walk or bike to South Beach. This spacious home is perfect for...Read more

Location: 
Katama
Sleeps: 
12
Bedrooms: 
5
Baths: 
3
Price Range:
$17,500 - $19,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
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5
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8
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15
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20
21
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23
24
25
26
27
28
29
30
 $17,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$17,500
6
7
8
9
10
11
12
$17,500
13
14
15
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18
19
$17,500
20
21
22
23
24
25
26
$17,500
27
28
29
30
31
 $17,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$17,500
3
4
5
6
7
8
9
$19,500
10
11
12
13
14
15
16
$19,500
17
18
19
20
21
22
23
$19,500
24
25
26
27
28
29
30
$18,000
31
 $15,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$15,500
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: 
$650 per week
Tax: State & Local: 
11.7

Pool Heated to 82 degrees, last week of June through first week of September included in rental rate

Pool Heat to 82 degrees, first three weeks of June and last three weeks of September additional $300.      

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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
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
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10
11
12
13
14
15
16
17
18
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20
21
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23
24
25
26
27
28
29
30
 $13,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$13,000
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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Luxurious Home located in The Preserve, 18 x 36 Heated Pool , Multiple Indoo/Outdoor Entertainment Areas

Welcome to this stunning, expansive luxury residence nestled within the exclusive enclave of homes known as The Preserve!

Situated on the outskirts of Oak Bluffs, The Preserve is a lovely community...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
4
Price Range:
$10,500 - $20,000
June 2025
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
 $18,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$18,000
6
7
8
9
10
11
12
$18,000
13
14
15
16
17
18
19
$18,000
20
21
22
23
24
25
26
$20,000
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
$18,500
31
 $11,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$11,500
7
8
9
10
11
12
13
$10,500
14
15
16
17
18
19
20
$10,500
21
22
23
24
25
26
27
$10,500
28
29
30
 
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

Pool Heated to 82 July and August weeks included in Rental Rate. 

Pool Heated to 82 June & September weeks additional $350 per week.  

 

The poolside spa maintains the same temperature as the pool itself, and the jets are not activated. However, should you desire, the spa can be heated for a duration of 4 hours daily, subject to an additional weekly charge. For more information, kindly reach out to the agent for further details.

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SPACIOUS LIGHTFILLED 3 BEDROOM, 3 BATH HOME, PRIVATE DECK WITH PATIO DINING, LOCATED IN QUIET COMMUNITY OF HOMES

Enjoy the best of the Island—the serenity of a secluded wooded sanctuary, the convenience, fun and shopping of the 3 Down Island towns (Oak Bluffs, Edgartown and Vineyard Haven), and easy access...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$3,500 - $5,200
June 2025
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
 $4,100
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,100
6
7
8
9
10
11
12
$4,100
13
14
15
16
17
18
19
$4,100
20
21
22
23
24
25
26
$4,100
27
28
29
30
31
 $4,900
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,900
3
4
5
6
7
8
9
$5,100
10
11
12
13
14
15
16
$5,100
17
18
19
20
21
22
23
$5,100
24
25
26
27
28
29
30
$4,900
31
 $4,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,500
7
8
9
10
11
12
13
$4,500
14
15
16
17
18
19
20
$4,000
21
22
23
24
25
26
27
$4,000
28
29
30
 $4,000
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

 

 

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Modern, Newly Renovated, Architecturally Significant Beach Cottage Design. Close to Town and Beaches, Tucked in the Lovely Community of Summer Homes, Waterview Farms!

Gorgeous all newly renovated and newly furnished mid-century beach cottage, now a modern vacation oasis designed by the prominent interior design firm, - Tersigni Palachek. This eloquent, yet beachy home offers...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,600 - $4,100
June 2025
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
 $6,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,500
6
7
8
9
10
11
12
$6,500
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$6,500
27
28
29
30
31
 $6,400
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,400
3
4
5
6
7
8
9
$6,600
10
11
12
13
14
15
16
$6,600
17
18
19
20
21
22
23
$6,600
24
25
26
27
28
29
30
$6,600
31
 $6,600
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,600
7
8
9
10
11
12
13
$4,100
14
15
16
17
18
19
20
$4,100
21
22
23
24
25
26
27
$4,100
28
29
30
 $2,600
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

Rate reduced for week 7/11-7/18 - see calendar for adjusted rates

 

Owner books Fri to Fri July & August weeks!

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Beautiful Long View Country House, Walk to Lambert's Cove Beach, Central A/C

Extended families will enjoy this lovely 5 bedroom, 3 bath home featuring expanded living space with a first-floor living room and second-floor family/tv room.  Spacious modern kitchen with prep island...Read more

Location: 
West Tisbury
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$3,200 - $8,300
June 2025
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
 $8,000
July 2025
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
$8,000
27
28
29
30
31
 $8,300
August 2025
SuMoTuWeThFrSaWeek
 1
2
$8,300
3
4
5
6
7
8
9
$8,300
10
11
12
13
14
15
16
$8,300
17
18
19
20
21
22
23
$8,300
24
25
26
27
28
29
30
$8,300
31
 $6,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,500
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
 $6,500
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

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