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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 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$11,000
6
7
8
9
10
11
12
$11,000
13
14
15
16
17
18
19
$11,000
20
21
22
23
24
25
26
$11,000
27
28
29
30
 $13,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$13,000
4
5
6
7
8
9
10
$13,000
11
12
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$13,000
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19
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24
$13,000
25
26
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29
30
31
$16,000
August 2027
SuMoTuWeThFrSaWeek
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2
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7
$16,000
8
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$16,000
15
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21
$16,000
22
23
24
25
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27
28
$14,000
29
30
31
 $11,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,000
5
6
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10
11
$8,000
12
13
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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 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 - $30,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$15,000
6
7
8
9
10
11
12
$15,000
13
14
15
16
17
18
19
$15,000
20
21
22
23
24
25
26
$15,000
27
28
29
30
 $20,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$20,000
4
5
6
7
8
9
10
$20,000
11
12
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$20,000
18
19
20
21
22
23
24
$25,000
25
26
27
28
29
30
31
$25,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$25,000
8
9
10
11
12
13
14
$25,000
15
16
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18
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20
21
$30,000
22
23
24
25
26
27
28
$30,000
29
30
31
 $20,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$20,000
5
6
7
8
9
10
11
$20,000
12
13
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15
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18
$20,000
19
20
21
22
23
24
25
$15,000
26
27
28
29
30
 $15,000
Clean Fee: 
$800 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. The owner will activate the spa, see additional cost below

2 hours per day,  additional $350 per week

4 hours per day,  additional $600 per week

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SPACIOUS LIGHTFILLED 3 BEDROOM, 3 BATH HOME, PRIVATE DECK WITH PATIO DINING, 7 MINUTE DRIVE TO THE CENTER OF OAK BLUFFS AND INKWELL BEACH

Experience the best of Island living—peaceful residential surroundings, the vibrant shops and attractions of the three Down Island towns (Oak Bluffs, Edgartown, and Vineyard Haven), and quick access to public...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$2,700 - $5,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,900
6
7
8
9
10
11
12
$3,900
13
14
15
16
17
18
19
$3,900
20
21
22
23
24
25
26
$4,300
27
28
29
30
 $4,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,500
4
5
6
7
8
9
10
$4,500
11
12
13
14
15
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17
$4,500
18
19
20
21
22
23
24
$4,500
25
26
27
28
29
30
31
$4,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,500
8
9
10
11
12
13
14
$5,500
15
16
17
18
19
20
21
$5,500
22
23
24
25
26
27
28
$5,500
29
30
31
 $5,200
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,200
5
6
7
8
9
10
11
$3,700
12
13
14
15
16
17
18
$3,200
19
20
21
22
23
24
25
$3,200
26
27
28
29
30
 $3,200
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 - $7,200
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
6
7
8
9
10
11
12
$3,500
13
14
15
16
17
18
19
$3,900
20
21
22
23
24
25
26
$3,900
27
28
29
30
 $6,400
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$6,400
4
5
6
7
8
9
10
$6,400
11
12
13
14
15
16
17
$6,400
18
19
20
21
22
23
24
$6,400
25
26
27
28
29
30
31
$6,400
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$7,200
8
9
10
11
12
13
14
$7,200
15
16
17
18
19
20
21
$7,200
22
23
24
25
26
27
28
$7,200
29
30
31
 $7,200
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,200
5
6
7
8
9
10
11
$2,700
12
13
14
15
16
17
18
$2,700
19
20
21
22
23
24
25
$2,700
26
27
28
29
30
 $2,700
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

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:
$6,900 - $8,500
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSa
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25
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30
31
August 2027
SuMoTuWeThFrSaWeek
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2
3
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$8,500
8
9
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11
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14
$8,500
15
16
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20
21
$8,500
22
23
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25
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27
28
$8,500
29
30
31
 
September 2027
SuMoTuWeThFrSa
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2
3
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25
26
27
28
29
30
 
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
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Lovely Cape Home, Newly Updated, Private Back Deck with Outdoor Dining & Grill, 3 Bedrooms w/AC and TV, 1.5 baths

Nestled on a serene lane in the outskirts of Vineyard Haven, this newly updated & charming Cape Style residence exudes chic charm. Step inside to discover an inviting open layout...Read more

Location: 
Vineyard Haven
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$3,000 - $4,400
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,000
6
7
8
9
10
11
12
$3,000
13
14
15
16
17
18
19
$3,000
20
21
22
23
24
25
26
$3,500
27
28
29
30
 $3,700
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,700
4
5
6
7
8
9
10
$3,700
11
12
13
14
15
16
17
$3,700
18
19
20
21
22
23
24
$3,700
25
26
27
28
29
30
31
$4,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,000
8
9
10
11
12
13
14
$4,400
15
16
17
18
19
20
21
$4,400
22
23
24
25
26
27
28
$4,000
29
30
31
 $3,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,500
5
6
7
8
9
10
11
$3,000
12
13
14
15
16
17
18
$3,000
19
20
21
22
23
24
25
$3,000
26
27
28
29
30
 $3,000
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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Exquisite New Contemporary Waterfront Home, Multiple Indoor& Outdoor Living Spaces with Waterviews.

This stunning luxury waterfront home, nestled on the Lagoon, offers breathtaking water views from every corner of the newly built residence. Enjoy the seamless transition between indoor and outdoor living...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
3
Baths: 
4
Price Range:
$12,500 - $14,000
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSa
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August 2027
SuMoTuWeThFrSa
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September 2027
SuMoTuWeThFrSa
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29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Owner requires two week minimum booking during months July & August

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Luxury 2-Bedroom Condo at Mariner’s Landing – Unit #3 of 8

Discover the perfect retreat just a short stroll from Edgartown Village Center. This condo offers easy access to scenic bike paths that lead to both the village center and the beautiful...Read more

Location: 
Edgartown
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$3,000 - $5,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,000
6
7
8
9
10
11
12
$3,000
13
14
15
16
17
18
19
$3,000
20
21
22
23
24
25
26
$3,100
27
28
29
30
 $4,200
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,200
4
5
6
7
8
9
10
$4,200
11
12
13
14
15
16
17
$4,200
18
19
20
21
22
23
24
$4,500
25
26
27
28
29
30
31
$4,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,000
8
9
10
11
12
13
14
$5,000
15
16
17
18
19
20
21
$5,000
22
23
24
25
26
27
28
$4,200
29
30
31
 $4,200
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,200
5
6
7
8
9
10
11
$3,100
12
13
14
15
16
17
18
$3,100
19
20
21
22
23
24
25
$3,000
26
27
28
29
30
 $3,000
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7
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New Modern Farmhouse Design, Great Location!, Wraparound Farmers Porch, Deck Area.

Beautiful new 4 bedroom home, 3.5 bath sleeps 8.  Ideally located just 2 miles from the center of Oak Bluffs and just minutes by car to the towns of Vineyard Haven and...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,100 - $6,900
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,800
6
7
8
9
10
11
12
$3,800
13
14
15
16
17
18
19
$3,800
20
21
22
23
24
25
26
$3,800
27
28
29
30
 $6,400
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$6,400
4
5
6
7
8
9
10
$6,400
11
12
13
14
15
16
17
$6,400
18
19
20
21
22
23
24
$6,400
25
26
27
28
29
30
31
$6,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,900
8
9
10
11
12
13
14
$6,900
15
16
17
18
19
20
21
$6,900
22
23
24
25
26
27
28
$6,900
29
30
31
 $6,900
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,900
5
6
7
8
9
10
11
$3,800
12
13
14
15
16
17
18
$3,800
19
20
21
22
23
24
25
$3,800
26
27
28
29
30
 $3,800
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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Contemporary 4 Bedroom, 4 Bath, Multiple Living Spaces, Walk to Oak Bluffs Center and Inkwell Beach-10 minutes

Perfect for extended families and friends, this spacious tri-level contemporary home offers multiple gathering spaces, comfortable accommodations, and an ideal location just a short stroll from the heart of Oak Bluffs....Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$4,000 - $7,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$4,000
13
14
15
16
17
18
19
$4,000
20
21
22
23
24
25
26
$4,500
27
28
29
30
 $5,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,500
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
$6,500
25
26
27
28
29
30
31
$6,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$7,500
8
9
10
11
12
13
14
$8,800
15
16
17
18
19
20
21
$8,800
22
23
24
25
26
27
28
$7,500
29
30
31
 $5,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,500
5
6
7
8
9
10
11
$4,000
12
13
14
15
16
17
18
$4,000
19
20
21
22
23
24
25
$4,000
26
27
28
29
30
 $4,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

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