Tucked away on a lovely parcel in the heart of Edgartown Village, this elegant modern farmhouse retreat offers a blend of sophistication and relaxed coastal living, with distant views of Nantucket...Read more
Luxury Retreat, Heart of Edgartown Village, Heated Salt Water Pool, 500 yards to Fuller St Beach, Two Blocks to Lighthouse Beach, 5 minute Walk to Village Center
Custom tri-level home with designer touches throughout. Features open concept main level with French doors leading to the pool and patio areas and to the portico with fireplace. Several living entertainment ...Read more
Stunning Luxury Home, Heated 18 x 42 Gunite Pool, Spectacular Yard & Patio Areas, Ideally Located with a 10 minute Walk to Village, 7 minute drive to South Beach
Contemporary, architect-designed coastal-style farmhouse, this luxurious vacation home will exceed your every expectation in amenity, quality, furnishings, and location. Situated in a distinctive enclave of eight luxury homes on 1-2...Read more
Location:
Edgartown
Sleeps:
9
Bedrooms:
5
Baths:
5
Price Range:
$10,000 - $28,000
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
$16,000
14
15
16
17
18
19
20
$20,000
21
22
23
24
25
26
27
$25,000
28
29
30
$30,000
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$30,000
5
6
7
8
9
10
11
$30,000
12
13
14
15
16
17
18
$28,000
19
20
21
22
23
24
25
$28,000
26
27
28
29
30
31
$35,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$35,000
2
3
4
5
6
7
8
$35,000
9
10
11
12
13
14
15
$35,000
16
17
18
19
20
21
22
$35,000
23
24
25
26
27
28
29
$24,000
30
31
$20,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$20,000
6
7
8
9
10
11
12
$14,000
13
14
15
16
17
18
19
$14,000
20
21
22
23
24
25
26
$14,000
27
28
29
30
Clean Fee:
$750 per week
Tax: State & Local:
11.7
Pool Heated to 81 degrees July & August, included in the rental rate
Pool Heated to 81 June, additional $400 per week propane fee.
Pool is not heated in September 2025 from 9/13 on.
Deluxe Family & Friends Compound, Heated Pool, 7 bedrooms 5.5 Baths
This exceptional estate is nestled in the prestigious Oyster Pond enclave, located on the outskirts of Edgartown. Set on expansive private grounds, this vacation retreat features 7 bedrooms and 5.5...Read more
Location:
Edgartown
Sleeps:
14
Bedrooms:
7
Baths:
5
Price Range:
$14,000 - $27,500
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
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
$15,500
28
29
30
$20,000
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$20,000
5
6
7
8
9
10
11
$20,000
12
13
14
15
16
17
18
$20,000
19
20
21
22
23
24
25
$20,000
26
27
28
29
30
31
$24,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$24,000
2
3
4
5
6
7
8
$27,500
9
10
11
12
13
14
15
$27,500
16
17
18
19
20
21
22
$24,000
23
24
25
26
27
28
29
$22,500
30
31
$18,500
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$18,500
6
7
8
9
10
11
12
$18,500
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
Tax: State & Local:
11.7
Pool is heated to 81 degrees and included in the rent July & August weeks. Off season May to October there is an additional fee for pool heat. Inquire with an agent for details
Sophisticated, Contemporary Vacation Retreat, Main & Guest House, Heated Pool, Outdoor Living Area, Pond Access for Paddle Boarding and Kayaking, Private Location
A light-filled, coastal-inspired luxury vacation home and guest house tucked in a private location featuring views of Watcha Pond, multiple living spaces, a gourmet kitchen, 4 bedrooms, 4 luxury bathrooms, and the ability to...Read more
Location:
West Tisbury
Sleeps:
8
Bedrooms:
4
Baths:
4
Price Range:
$15,000 - $26,000
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
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
$26,000
28
29
30
$26,000
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$26,000
5
6
7
8
9
10
11
$26,000
12
13
14
15
16
17
18
$26,000
19
20
21
22
23
24
25
$26,000
26
27
28
29
30
31
$26,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$26,000
2
3
4
5
6
7
8
$26,000
9
10
11
12
13
14
15
$26,000
16
17
18
19
20
21
22
$26,000
23
24
25
26
27
28
29
$26,000
30
31
$22,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$22,000
6
7
8
9
10
11
12
$19,000
13
14
15
16
17
18
19
$19,000
20
21
22
23
24
25
26
$19,000
27
28
29
30
Clean Fee:
$850 per week
Tax: State & Local:
11.7
Pool heated to 81 degrees included in rental rate July to 8/26. Pool heated to 81 degrees June & September weeks additional $300 propane surcharge weekly.
Essence of Chilmark Living, Tucked on High Knoll Providing Expansive Waterviews of the Atlantic, Luxurious Custom Design, Lush Gardens, 5 minute Drive to Lucy Vincent Beach
Experience the essence of Martha's Vineyard with family and friends at this exceptional home nestled on Peaked Hill in Chilmark, offering breathtaking views of the Atlantic. Set on 8 acres...Read more
Stunning New Home with Heated Pool. Walk to Edgartown Village Center, 5 Minute Drive to Beach
Outstanding Luxury Home with multiple living spaces both indoor and outdoor. 4 Bedrooms, 3.5 baths, sleeps 10. Heated pool, large patio with outdoor dining and living area, and chaise lounge chairs (patio...Read more
Location:
Edgartown
Sleeps:
10
Bedrooms:
4
Baths:
3
Price Range:
$10,000 - $25,500
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$10,000
7
8
9
10
11
12
13
$10,000
14
15
16
17
18
19
20
$18,000
21
22
23
24
25
26
27
$25,500
28
29
30
$25,500
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$25,500
5
6
7
8
9
10
11
$25,500
12
13
14
15
16
17
18
$25,500
19
20
21
22
23
24
25
$25,500
26
27
28
29
30
31
$25,500
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$25,500
2
3
4
5
6
7
8
$25,500
9
10
11
12
13
14
15
$25,500
16
17
18
19
20
21
22
$25,500
23
24
25
26
27
28
29
$18,000
30
31
$12,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$12,000
6
7
8
9
10
11
12
$12,000
13
14
15
16
17
18
19
$12,000
20
21
22
23
24
25
26
$12,000
27
28
29
30
$10,000
Clean Fee:
$650 per week
Tax: State & Local:
11.7
Pool Heated to 81, included in rental rate July & August weeks
Pool Heated to 81 June & September weeks additional $350 per week. Pool Heat in May and October, additional cost. Please inquire with your agent!
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
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:
$850 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!
Light House is a Luxurious Harborfront Home and Part of a 2 House Compound Village Center, Walk to Light House and Fuller St Beaches
The Light House is part of a two-house luxury compound located waterfront on spectacular Edgartown Harbor with stunning views. This unique residence was designed by one of the Island's leading architectural designers and has...Read more
THE FERRY HOUSE IS A LUXURIOUS HARBORFRONT HOME, AND PART OF A 2 HOUSE COMPOUND, VILLAGE CENTER, WALK TO LIGHT HOUSE AND FULLER ST BEACHES
Welcome to luxury living dockside in this spectacular 3 bedroom, 3 bath restored boathouse. The Ferry House has been featured in Architectural Digest. Attention to detail, design, and craftsmanship are evident...Read more
Exquisite New Luxurious Home, Tucked in the Private Enclave, Known as -The Preserve, Heated Saltwater Pool 18' x 45, Screened Porch, Propane Fire pit with Adirondack Seating, Designer Interior
"The Preserve" in Oak Bluffs is a desirable enclave of homes that offers a serene and alluring living environment. This expansive luxury home designed by noted architect Chuck Sullivan was completed...Read more
Location:
Oak Bluffs
Sleeps:
12
Bedrooms:
6
Baths:
5
Price Range:
$17,000 - $25,000
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$20,000
7
8
9
10
11
12
13
$20,000
14
15
16
17
18
19
20
$22,500
21
22
23
24
25
26
27
$25,000
28
29
30
$27,000
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$27,000
5
6
7
8
9
10
11
$27,000
12
13
14
15
16
17
18
$27,000
19
20
21
22
23
24
25
$27,000
26
27
28
29
30
31
$28,500
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$28,500
2
3
4
5
6
7
8
$30,000
9
10
11
12
13
14
15
$32,500
16
17
18
19
20
21
22
$32,500
23
24
25
26
27
28
29
$30,000
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
$20,000
13
14
15
16
17
18
19
$18,500
20
21
22
23
24
25
26
$18,500
27
28
29
30
$17,000
Clean Fee:
$960 per week
Tax: State & Local:
11.7
Pool Heated to 82 degrees July & August weeks, included in the rental rate
Pool Heated to 82 degrees June & September weeks, additional $300 per week surcharge
Luxury Gambrel Home. Heated Pool, Bluestone Patio Surround, Patio Dining, Walk to Town, 4 Bedrooms, 3.5 Baths
Unwind with family and friends in this newly constructed vacation home, featuring a heated pool and ideally situated on a peaceful lane, just a short stroll to the village center....Read more
Perfect Family Compound in Katama, Heated Pool, Tennis Courts. Main and Guest House., 1.5 miles to Soutn Beach and 1.5 Miles to Edgartown Village
Edgartown, Katama Area, Family Compound
Ideally located halfway between Edgartown Center and South Beach, this wooded lot strikes a balance between privacy and convenience. Take the bike path running alongside...Read more
Location:
Katama
Sleeps:
20
Bedrooms:
11
Baths:
7
Price Range:
$9,500 - $24,000
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
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
$18,500
28
29
30
$18,500
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$18,500
5
6
7
8
9
10
11
$18,500
12
13
14
15
16
17
18
$18,500
19
20
21
22
23
24
25
$24,000
26
27
28
29
30
31
$24,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$24,000
2
3
4
5
6
7
8
$24,000
9
10
11
12
13
14
15
$24,000
16
17
18
19
20
21
22
$18,500
23
24
25
26
27
28
29
$18,500
30
31
$12,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$12,000
6
7
8
9
10
11
12
$12,000
13
14
15
16
17
18
19
$12,000
20
21
22
23
24
25
26
$12,000
27
28
29
30
$11,000
Clean Fee:
$1300 per week
Tax: State & Local:
11.7
Pool Heated to 82, July & August weeks included in Rental Rate
Pool Heated to 82 May, June, Sept & October weeks additional $350 per week surcharge.
