The Beach House There are few homes anywhere on the island directly on a sandy swimming beach like Beach House. If you love a sunset, and water views that seemingly never...Read more
Makonikey, Water View, Walk to Private Association Beach, Large Yard Area.
Located in Makonikey, a private enclave of homes on the North Shore.
Beautifully maintained four-bedroom vacation home with water views. Just a short walk or drive to private Makonikey association beach, This...Read more
Spacious Oak Bluffs Contemporary Home, 4 Bedrooms & 4 Baths, Quiet Private Location in Bayes Hill Community of Homes
Privately situated on the outskirts of Oak Bluffs, yet centrally located to towns and beaches. The home features a large patio area with outdoor dining and grill area and a spacious...Read more
Exquisite New Home with Heated Pool, 18 x 38, 4 Bedrooms, 3.5 Baths, Multiple Living Areas
Note for 2025: Additional furnishings, including a large TV for the family room, new bedding, and window treatments, will be arriving in April and May 2025. The spacious deck will...Read more
Location:
Edgartown
Sleeps:
10
Bedrooms:
4
Baths:
3
Price Range:
$7,500 - $22,000
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$14,000
7
8
9
10
11
12
13
$14,000
14
15
16
17
18
19
20
$14,000
21
22
23
24
25
26
27
$14,000
28
29
30
$15,000
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$15,000
5
6
7
8
9
10
11
$15,000
12
13
14
15
16
17
18
$15,000
19
20
21
22
23
24
25
$15,000
26
27
28
29
30
31
$15,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$15,000
2
3
4
5
6
7
8
$22,000
9
10
11
12
13
14
15
$22,000
16
17
18
19
20
21
22
$22,000
23
24
25
26
27
28
29
$22,000
30
31
$10,500
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$10,500
6
7
8
9
10
11
12
$7,500
13
14
15
16
17
18
19
$7,500
20
21
22
23
24
25
26
$7,500
27
28
29
30
$7,500
Clean Fee:
$600 per week
Tax: State & Local:
11.7
Pool Heated to 81 degrees, included in the rental rate July & August weeks.
Pool Heated to 81 degrees, June & September weeks, additional propane surcharge $300 per week.
Pool Spa will be heated to 101 degrees, 4 hours per day 6/10 pm, included in the rental rate July & August weeks.
Pool Spa heated to 101 degrees June & September weeks, 4 hours per day 6 to 10 pm, additional $200 per week.
Charming & Cozy 2 Bedroom, 2 Bath Home, West Chop area of Vineyard Haven, Located on a Quiet Street, Close to Town & Beach
Ideally located in the West Chop woods area of Vineyard Haven, just 1 mile to town center and the business district, and a 10 to 15-minute drive to various public...Read more
The Retreat at Towanticut Where Coastal Elegance Meets Island Serenity, 3 Bedrooms, 2 Baths, Landscaped Yard, Deck Dining Area
Welcome to The Retreat at Towanticut— a chic coastal escape where upscale comfort meets effortless Vineyard charm. Nestled in the heart of Oak Bluffs and just a 15-minute stroll to Circuit Avenue...Read more
Luxury Retreat Chilmark, Key to Quansoo Private Association Beach, Heated Pool, Stone Patio, Pool Pavillion, Propane Fire Pit, Set on 7.5 private acres
New for 2024: Heated Pool with Patio Surround, Propane Fire Pit, Post and Beam Pool Pavillion with outdoor kitchen hosting 36" Lynx Grill, Lynx Sink, Power Burner, undercounter Fridge and dishwasher, Raised...Read more
Location:
Chilmark
Sleeps:
8
Bedrooms:
4
Baths:
3
Price Range:
$15,000 - $25,000
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
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
$22,500
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$22,500
5
6
7
8
9
10
11
$22,500
12
13
14
15
16
17
18
$22,500
19
20
21
22
23
24
25
$22,500
26
27
28
29
30
31
$25,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$25,000
2
3
4
5
6
7
8
$25,000
9
10
11
12
13
14
15
$25,000
16
17
18
19
20
21
22
$25,000
23
24
25
26
27
28
29
$25,000
30
31
$22,500
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$22,500
6
7
8
9
10
11
12
$20,500
13
14
15
16
17
18
19
$18,500
20
21
22
23
24
25
26
$18,500
27
28
29
30
$18,500
Clean Fee:
$850 per week ($650 interim clean)
Tax: State & Local:
11.7
Pool will be heated to 82 degrees July and August included in rental rate.
Pool Heated to 82 degrees June & Sept weeks $300/week
Beautiful Oak Bluffs home just blocks from the Center of Town, Ocean Park and Inkwell Beach.
Note: the kitchen is being completely remodeled for summer 2024 and will have all new high-end appliances, Subzero, Thermador, and new cabinets, and counters.
Stunning Waterfront Home on the Lagoon, Complete Renovation and Professionally Decorated. Private Beach Area and Dock, Perfect Retreat for Extended Families, Walk to Town. Swim, Sun, Kayak or Bring your own boat.
Exquisite waterfront family compound sleeps 12, with 270-degree water view of the Lagoon, 85' of sandy beach on the lagoon, and a private dock for boaters. Private dock (12' draft) with mooring and private sandy...Read more
Location:
Vineyard Haven
Sleeps:
12
Bedrooms:
6
Baths:
4
Price Range:
$8,500 - $25,000
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$14,000
7
8
9
10
11
12
13
$14,000
14
15
16
17
18
19
20
$14,000
21
22
23
24
25
26
27
$14,000
28
29
30
$19,250
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$19,250
5
6
7
8
9
10
11
$19,250
12
13
14
15
16
17
18
$19,250
19
20
21
22
23
24
25
$22,500
26
27
28
29
30
31
$25,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$25,000
2
3
4
5
6
7
8
$25,000
9
10
11
12
13
14
15
$25,000
16
17
18
19
20
21
22
$25,000
23
24
25
26
27
28
29
$22,000
30
31
$14,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$14,000
6
7
8
9
10
11
12
$12,000
13
14
15
16
17
18
19
$11,000
20
21
22
23
24
25
26
$11,000
27
28
29
30
$11,000
Clean Fee:
$750 per week
Tax: State & Local:
11.7
Private Dock plus Mooring that draws 12 feet. If you plan to bring a boat please speak with the agent for details as must be approved by owner!
New Tri Level Luxury Home, Heated Pool with Bluestone Patio Surround
Location location!
Just 1 mile from Oak Bluffs center this stunning 5 bedroom, 4.5 bath features a gunite pool with a bluestone patio surround, sure to be the focal point...Read more
Location:
Oak Bluffs
Sleeps:
10
Bedrooms:
5
Baths:
4
Price Range:
$7,500 - $17,600
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
$13,600
21
22
23
24
25
26
27
$15,300
28
29
30
$15,700
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$15,700
5
6
7
8
9
10
11
$15,700
12
13
14
15
16
17
18
$15,700
19
20
21
22
23
24
25
$16,800
26
27
28
29
30
31
$16,800
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$16,800
2
3
4
5
6
7
8
$17,600
9
10
11
12
13
14
15
$17,600
16
17
18
19
20
21
22
$17,600
23
24
25
26
27
28
29
$17,600
30
31
$10,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$10,000
6
7
8
9
10
11
12
$7,500
13
14
15
16
17
18
19
$7,500
20
21
22
23
24
25
26
$7,500
27
28
29
30
$7,500
Clean Fee:
$850 per week
Tax: State & Local:
11.7
Pool Heated to 81 included in rental rate, July and August weeks
June & September weeks to 81 degrees additional $500 fee. Higher temp upon request additional fee
Notice: Ring doorbell cameras are located on the front entry door and door on the left/parking side of the house:
