Vacation Rentals

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Beautiful Upscale Contemporary Home, Designer Details Throughout, 4 Bedrooms, 4.5 Baths, Muliple Living Areas

Discover this stunning tri-level vacation home nestled in a peaceful community just on the outskirts of Oak Bluffs and minutes away from Oak Bluffs center, Edgartown Village, downtown Vineyard Haven, and several...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
4
Price Range:
$10 - $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
$7,500
29
30
 $7,800
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,800
6
7
8
9
10
11
12
$7,800
13
14
15
16
17
18
19
$7,800
20
21
22
23
24
25
26
$7,800
27
28
29
30
31
 $8,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$8,000
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
$7,500
31
 
September 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
 
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
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Newly Refurbished Contemporary Home, Beautifully Furnished, Privately Situated with Large Yard and Wraparound Farmer’s Porch, Dodger’s Hole Area

A great vacation begins with a great vacation home. This spacious home set on a private, large landscaped lot is sure to please. The summer wrap around porch is the perfect...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$10 - $7,150
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,750
8
9
10
11
12
13
14
$6,750
15
16
17
18
19
20
21
$6,750
22
23
24
25
26
27
28
$6,750
29
30
 $6,950
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,950
6
7
8
9
10
11
12
$6,950
13
14
15
16
17
18
19
$6,950
20
21
22
23
24
25
26
$6,950
27
28
29
30
31
 $7,150
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,150
3
4
5
6
7
8
9
$7,150
10
11
12
13
14
15
16
$7,150
17
18
19
20
21
22
23
$7,150
24
25
26
27
28
29
30
$7,150
31
 $6,550
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,550
7
8
9
10
11
12
13
$6,550
14
15
16
17
18
19
20
$6,550
21
22
23
24
25
26
27
$6,550
28
29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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Katama Area, Stylish Designer Luxury, Bike to South Beach and Village Areas, Spacious Bluestone Patio overlooks Private Yard Area

All newly renovated and beautifully furnished, the main level of this traditional style floor plan includes, - hardwood floors throughout, bead board accents, a living room with balcony, TV center,...Read more

Location: 
Katama
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$10 - $8,900
June 2025
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
$7,500
22
23
24
25
26
27
28
$8,900
29
30
 $8,900
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,900
6
7
8
9
10
11
12
$8,900
13
14
15
16
17
18
19
$8,900
20
21
22
23
24
25
26
$8,900
27
28
29
30
31
 $8,900
August 2025
SuMoTuWeThFrSaWeek
 1
2
$8,900
3
4
5
6
7
8
9
$8,900
10
11
12
13
14
15
16
$8,900
17
18
19
20
21
22
23
$8,900
24
25
26
27
28
29
30
$8,900
31
 $8,900
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$8,900
7
8
9
10
11
12
13
$6,300
14
15
16
17
18
19
20
$4,800
21
22
23
24
25
26
27
$4,800
28
29
30
 $4,000
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Owner requires minimum of 2 week bookings

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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:
$10 - $57,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$29,000
8
9
10
11
12
13
14
$29,000
15
16
17
18
19
20
21
$45,000
22
23
24
25
26
27
28
$57,000
29
30
 $57,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$57,000
6
7
8
9
10
11
12
$57,000
13
14
15
16
17
18
19
$57,000
20
21
22
23
24
25
26
$57,000
27
28
29
30
31
 $57,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$57,000
3
4
5
6
7
8
9
$57,000
10
11
12
13
14
15
16
$57,000
17
18
19
20
21
22
23
$57,000
24
25
26
27
28
29
30
$57,000
31
 $57,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$57,000
7
8
9
10
11
12
13
$38,000
14
15
16
17
18
19
20
$38,000
21
22
23
24
25
26
27
$38,000
28
29
30
 $22,000
Clean Fee: 
$1000 per week
Tax: State & Local: 
11.7

 

 

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Long Point Beach Area, Heated Pool, Large Patio with Living and Dining Areas, Gorgeous Contemporary Coastal Interior, Large Private Yard

Gorgeous all newly updated 4 bedroom home with central AC, privately tucked away in the Long Point Beach area of West Tisbury, a family-friendly community of lovely homes, and only minutes away...Read more

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

Pool heated by aqua-solar panels throughout the rental period.  Specific request for 82 degrees by use of propane heat incurs a $400 per week surcharge.

 

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Water Views, Heated Pool , Walk/Drive to Private Association Waterfront, 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:
$10 - $14,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$7,500
8
9
10
11
12
13
14
$7,500
15
16
17
18
19
20
21
$14,500
22
23
24
25
26
27
28
$14,500
29
30
 $14,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$14,500
6
7
8
9
10
11
12
$14,500
13
14
15
16
17
18
19
$14,500
20
21
22
23
24
25
26
$14,500
27
28
29
30
31
 $14,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$14,500
3
4
5
6
7
8
9
$14,500
10
11
12
13
14
15
16
$14,500
17
18
19
20
21
22
23
$14,500
24
25
26
27
28
29
30
$14,500
31
 $14,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$14,500
7
8
9
10
11
12
13
$14,500
14
15
16
17
18
19
20
$14,500
21
22
23
24
25
26
27
$14,500
28
29
30
 $14,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Rates reduced for weeks 5/23 - 6/15 (pool heat included for these dates) - see calendar for adjusted rates

 

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 Katama Home, Heated Pool, Large Private Pool Patio and Landscaped Yard, Screened Porch and Expansive Deck, Located Just one mile to South Beach

Gorgeous home in the Katama area of Edgartown with a heated pool.  Ideally situated midway between South Beach and Edgartown village area!  Bike paths at the end of the street provide an easy bike ride...Read more

Location: 
Katama
Sleeps: 
10
Bedrooms: 
5
Baths: 
4
Price Range:
$10 - $10
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$8,000
8
9
10
11
12
13
14
$8,000
15
16
17
18
19
20
21
$8,000
22
23
24
25
26
27
28
$15,000
29
30
 $17,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$17,000
6
7
8
9
10
11
12
$17,000
13
14
15
16
17
18
19
$17,000
20
21
22
23
24
25
26
$17,000
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
$15,000
31
 $15,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$15,000
7
8
9
10
11
12
13
$15,000
14
15
16
17
18
19
20
$15,000
21
22
23
24
25
26
27
$15,000
28
29
30
 
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

 Pool heat included in rental rate in July & August

June and September pool heat is an additional cost to the renter of $300 per week

 

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Close to Edgartown Center and Beaches, Bike Paths 2/10 mile from house, Large and Private Deck, Central AC

This lovely 3 bedroom, 2.5 bath home features open concept living, dining, and kitchen areas. The spacious living and dining area opens via glass sliders to a large and private 20 x 40 ft...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $4,700
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,100
8
9
10
11
12
13
14
$2,300
15
16
17
18
19
20
21
$2,300
22
23
24
25
26
27
28
$3,270
29
30
 $3,270
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,270
6
7
8
9
10
11
12
$3,270
13
14
15
16
17
18
19
$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
31
 $4,700
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,700
3
4
5
6
7
8
9
$4,700
10
11
12
13
14
15
16
$4,700
17
18
19
20
21
22
23
$4,700
24
25
26
27
28
29
30
$4,700
31
 $2,400
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,400
7
8
9
10
11
12
13
$2,300
14
15
16
17
18
19
20
$2,300
21
22
23
24
25
26
27
$2,300
28
29
30
 $2,000
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

Ferry Tickets availalbe for weeks 7/26-8/2, 8/16-8/23, 8/23-8/30 - please inquire

 

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

Exceptional Rental Offering: Stunning 6-Bedroom, 5.5-Bath Home in West Chop, Vineyard Haven

Experience the epitome of summer luxury living in this exquisite 6-bedroom, 5.5-bath home nestled in the desirable West...Read more

Location: 
Vineyard Haven
Sleeps: 
13
Bedrooms: 
6
Baths: 
5
Price Range:
$10 - $35,000
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
 $25,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$25,000
6
7
8
9
10
11
12
$25,000
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
6
7
8
9
$35,000
10
11
12
13
14
15
16
$35,000
17
18
19
20
21
22
23
$35,000
24
25
26
27
28
29
30
$35,000
31
 $25,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$25,000
7
8
9
10
11
12
13
$18,000
14
15
16
17
18
19
20
$18,000
21
22
23
24
25
26
27
$16,000
28
29
30
 $14,000
Clean Fee: 
$1750 per week
Tax: State & Local: 
11.7

Ferry Tickets available for weeks 6/29-7/6, 7/6-7/13, 7/13-7/20, 7/20-7/27, 8/17-8/24 (2 tix), 8/24-8/31 - please inquire!

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

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