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52 properties available
Luxurious new construction in the prestigious Deep Bottom neighborhood with five en Suite bedrooms, including two primary suites, one on each floor, and plenty of space to spread out. When you walk into the foyer and see through the living area to the deck and pool beyond you know a serene and peaceful vacation awaits.
Cook in the well-appoint
$24,000.00 - $30,000.00 / per week + taxes and fees
5
beds
5
Full,
1
Half Bath
sleeps
10
Pets Not Allowed
No Events/Gatherings
West Tisbury 1105
Luxurious new construction in the prestigious Deep Bottom neighborhood with five en Suite bedrooms, including two primary suites, one on each floor, a... Read More
Luxurious new construction in the prestigious Deep Bottom neighborhood with five en Suite bedrooms, including two primary suites, one on each floor, a... Read More
June 2026
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| 1 | 2 | 3 | 4 | 5 | $26,000 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | $26,000 13 |
| 14 | 15 | 16 | 17 | 18 | 19 | $26,000 20 |
| 21 | 22 | 23 | 24 | 25 | 26 | $26,000 27 |
| 28 | 29 | 30 |
July 2026
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| 1 | 2 | 3 | $28,000 4 | |||
| 5 | 6 | 7 | 8 | 9 | 10 | $28,000 11 |
| 12 | 13 | 14 | 15 | 16 | 17 | $28,000 18 |
| 19 | 20 | 21 | 22 | 23 | 24 | $30,000 25 |
| 26 | 27 | 28 | 29 | 30 | 31 |
August 2026
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| 1 | ||||||
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| 9 | 10 | 11 | 12 | 13 | 14 | $30,000 15 |
| 16 | 17 | 18 | 19 | 20 | 21 | $30,000 22 |
| 23 | 24 | 25 | 26 | 27 | 28 | $30,000 29 |
| 30 | 31 |
Available
Unavailable
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Experience the epitome of luxury at this estate in the heart of Katama's most sought-after enclave, where over 6,700 square feet of impeccably curated living space invite you to indulge in a lifestyle reminiscent of a five-star retreat. This five-bedroom residence seamlessly blends timeless elegance with contemporary comfort. The interiors are all
$25,000.00 - $50,000.00 / per week + taxes and fees
5
beds
6
Full,
2
Half Bath
sleeps
10
Pets Considered
No Events/Gatherings
Edgartown Katama 673
Experience the epitome of luxury at this estate in the heart of Katama's most sought-after enclave, where over 6,700 square feet of impeccably curated... Read More
Experience the epitome of luxury at this estate in the heart of Katama's most sought-after enclave, where over 6,700 square feet of impeccably curated... Read More
June 2026
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| 1 | 2 | 3 | 4 | 5 | $35,000 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | $35,000 13 |
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July 2026
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| 19 | 20 | 21 | 22 | 23 | 24 | $50,000 25 |
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August 2026
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| 9 | 10 | 11 | 12 | 13 | 14 | $50,000 15 |
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| 23 | 24 | 25 | 26 | 27 | 28 | 29 |
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Available
Unavailable
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Stunning and immaculate 4500 square foot, 5 bedroom, custom Field Club home is waiting for your enjoyment. Inside you will find an open floor plan that extends the full length of the home. A large fully equipped chefs kitchen with a working island with access to ample seating, which spills to either indoor or outdoor dining just steps away. The f
$35,000.00 / per week + taxes and fees
5
beds
7
Full Bath
sleeps
10
Pets Not Allowed
No Events/Gatherings
Edgartown Katama 601
Stunning and immaculate 4500 square foot, 5 bedroom, custom Field Club home is waiting for your enjoyment. Inside you will find an open floor plan t... Read More
Stunning and immaculate 4500 square foot, 5 bedroom, custom Field Club home is waiting for your enjoyment. Inside you will find an open floor plan t... Read More
June 2026
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July 2026
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August 2026
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Available
Unavailable
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Welcome to this stunning 5-bedroom, 4.5-bathroom home located just outside Edgartown Village. This remarkable property is the ideal retreat for groups of up to 12 guests. Upon entering, you'll be welcomed by a spacious open-concept layout that seamlessly combines the kitchen, dining, and living areas. With lofty ceilings and an abundance of natural
$30,000.00 - $35,000.00 / per week + taxes and fees
5
beds
4
Full,
1
Half Bath
sleeps
12
Pets Not Allowed
No Events/Gatherings
Edgartown Downtown 9
Welcome to this stunning 5-bedroom, 4.5-bathroom home located just outside Edgartown Village. This remarkable property is the ideal retreat for groups... Read More
Welcome to this stunning 5-bedroom, 4.5-bathroom home located just outside Edgartown Village. This remarkable property is the ideal retreat for groups... Read More
June 2026
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July 2026
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August 2026
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| 23 | 24 | 25 | 26 | 27 | 28 | $35,000 29 |
| 30 | 31 |
Available
Unavailable
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Check-Out
Waterfront West Chop property overlooking Vineyard Sound. This expansive single-story home with separate second-floor apartment and short path to private beach, has plenty of room for everyone. Begin the day in the well appropriate kitchen, eat in the breakfast nook or the nearby screened in porch, both facing the water. Through the butler's pant
$17,500.00 - $28,000.00 / per week + taxes and fees
6
beds
5
Full Bath
sleeps
12
Pets Considered
No Events/Gatherings
Vineyard Haven 910
Waterfront West Chop property overlooking Vineyard Sound. This expansive single-story home with separate second-floor apartment and short path to pri... Read More
Waterfront West Chop property overlooking Vineyard Sound. This expansive single-story home with separate second-floor apartment and short path to pri... Read More
June 2026
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July 2026
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August 2026
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| 23 | 24 | 25 | 26 | 27 | 28 | $28,000 29 |
| 30 | 31 |
Available
Unavailable
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Check-Out
One of the most beautiful homes on North Water Street -- this seven bedroom historic Captain's Home, designed by Tracker Interiors, features multiple living spaces, game rooms and state of the art luxury. Pool in backyard. Outdoor dining for 10.
$25,000.00 - $45,000.00 / per week + taxes and fees
5
beds
5
Full,
1
Half Bath
sleeps
14
Pets Considered
No Events/Gatherings
Edgartown Downtown 15
One of the most beautiful homes on North Water Street -- this seven bedroom historic Captain's Home, designed by Tracker Interiors, features multiple ... Read More
One of the most beautiful homes on North Water Street -- this seven bedroom historic Captain's Home, designed by Tracker Interiors, features multiple ... Read More
June 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | $30,000 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | $45,000 13 |
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| 28 | 29 | 30 |
July 2026
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August 2026
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| 16 | 17 | 18 | 19 | 20 | 21 | 22 |
| 23 | 24 | 25 | 26 | 27 | 28 | $35,000 29 |
| 30 | 31 |
Available
Unavailable
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Check-Out
A matriarch among Edgartown waterfront homes with sweeping views along Edgartown Harbor says it all. Offering a private beach and private dock, a house this perfect, a life this easy - could hardly be imagined, let alone actually exist - until now. Featuring a single level design and a floorplan which follows the curve of the shore, and large windo
$10,000.00 - $31,500.00 / per week + taxes and fees
4
beds
3
Full Bath
sleeps
8
Pets Not Allowed
No Events/Gatherings
Edgartown Downtown 77
A matriarch among Edgartown waterfront homes with sweeping views along Edgartown Harbor says it all. Offering a private beach and private dock, a hous... Read More
A matriarch among Edgartown waterfront homes with sweeping views along Edgartown Harbor says it all. Offering a private beach and private dock, a hous... Read More
June 2026
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July 2026
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August 2026
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| 16 | 17 | 18 | 19 | 20 | 21 | $18,500 22 |
| 23 | 24 | 25 | 26 | 27 | 28 | 29 |
| 30 | 31 |
Available
Unavailable
Check-In
Check-Out
Edgartown 7747
... Read More
... Read More
June 2026
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July 2026
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| 19 | 20 | 21 | 22 | 23 | 24 | $28,000 25 |
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August 2026
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Available
Unavailable
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No detail was overlooked in the design of this stunning five-bedroom home set on the hill. This home offers comfort and style and features rich countertops, stainless steel appliances, and an open floor plan that flows effortlessly between the kitchen, dining, and living areas. Three of the five bedrooms are en-suites, and the third-floor media and
$20,000.00 - $40,000.00 / per week + taxes and fees
5
beds
5
Full,
1
Half Bath
sleeps
12
Pets Not Allowed
No Events/Gatherings
Edgartown Downtown 123
No detail was overlooked in the design of this stunning five-bedroom home set on the hill. This home offers comfort and style and features rich counte... Read More
No detail was overlooked in the design of this stunning five-bedroom home set on the hill. This home offers comfort and style and features rich counte... Read More
June 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | $25,000 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | $25,000 13 |
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July 2026
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| 5 | 6 | 7 | 8 | 9 | 10 | $38,500 11 |
| 12 | 13 | 14 | 15 | 16 | 17 | $38,500 18 |
| 19 | 20 | 21 | 22 | 23 | 24 | $38,500 25 |
| 26 | 27 | 28 | 29 | 30 | 31 |
August 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
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| 16 | 17 | 18 | 19 | 20 | 21 | 22 |
| 23 | 24 | 25 | 26 | 27 | 28 | $40,000 29 |
| 30 | 31 |
Available
Unavailable
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Check-Out
Brand new to the rental market: a new rendition of a classic Chappy home with a private dock and beach access -- renovations include an interior refresh: crisp white walls and vaulted ceilings, new bathrooms, air conditioning, all new furnishings - understated luxury, surrounded by 180-degree water views over Edgartown Harbor and Cape Pogue from th
$8,000.00 - $26,500.00 / per week + taxes and fees
5
beds
2
Full Bath
sleeps
10
Pets Not Allowed
No Events/Gatherings
Edgartown Chappaquiddick 305
Brand new to the rental market: a new rendition of a classic Chappy home with a private dock and beach access -- renovations include an interior refre... Read More
Brand new to the rental market: a new rendition of a classic Chappy home with a private dock and beach access -- renovations include an interior refre... Read More
June 2026
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July 2026
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August 2026
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Available
Unavailable
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Imagine indulging in luxury in this stunning four-bedroom home in Katama, just about a mile from downtown Edgartown and two miles from South Beach. The first floor features spacious living and dining areas and a beautiful eat-in kitchen. The primary bedroom is a true oasis, complete with a soaking tub in the en-suite bathroom and direct access to t
$7,000.00 - $28,000.00 / per week + taxes and fees
4
beds
5
Full Bath
sleeps
9
Pets Not Allowed
No Events/Gatherings
Edgartown 591
Imagine indulging in luxury in this stunning four-bedroom home in Katama, just about a mile from downtown Edgartown and two miles from South Beach. Th... Read More
Imagine indulging in luxury in this stunning four-bedroom home in Katama, just about a mile from downtown Edgartown and two miles from South Beach. Th... Read More
June 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | $12,250 6 | |
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| 21 | 22 | 23 | 24 | 25 | 26 | $22,000 27 |
| 28 | 29 | 30 |
July 2026
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|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | |||
| 5 | 6 | 7 | 8 | 9 | 10 | $22,000 11 |
| 12 | 13 | 14 | 15 | 16 | 17 | 18 |
| 19 | 20 | 21 | 22 | 23 | 24 | $25,000 25 |
| 26 | 27 | 28 | 29 | 30 | 31 |
August 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
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| 23 | 24 | 25 | 26 | 27 | 28 | $14,000 29 |
| 30 | 31 |
Available
Unavailable
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Check-Out
Located approximately 0.05 miles from the heart of downtown Edgartown, this beautifully designed and elegantly furnished five-bedroom coastal farmhouse offers a spacious first-floor living area. The large chef's kitchen features a prep island, granite countertops, Le Creuset cookware, a wine fridge, two dishwashers, and commercial-grade stainless s
$14,000.00 - $35,000.00 / per week + taxes and fees
5
beds
4
Full,
1
Half Bath
sleeps
10
Pets Not Allowed
No Events/Gatherings
Edgartown Katama 522
Located approximately 0.05 miles from the heart of downtown Edgartown, this beautifully designed and elegantly furnished five-bedroom coastal farmhous... Read More
Located approximately 0.05 miles from the heart of downtown Edgartown, this beautifully designed and elegantly furnished five-bedroom coastal farmhous... Read More
June 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | $16,000 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | 13 |
| 14 | 15 | 16 | 17 | 18 | 19 | $24,000 20 |
| 21 | 22 | 23 | 24 | 25 | 26 | $25,000 27 |
| 28 | 29 | 30 |
July 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | $30,000 4 | |||
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August 2026
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Available
Unavailable
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