Martha's Vineyard Vacation Rentals - Homes with Pools
143 properties available
This spacious 5 Bedroom home with a brand-new 20x60 saltwater pool and 8x12 hot tub is the ultimate Chappy getaway. Walk into the main level and you will find 4 of the 5 bedrooms, 2 full bathrooms and comfortable living space. Upstairs is the main living area, open concept kitchen, dining space, and primary en suite bedroom which all offer stunning
$12,000.00 - $17,000.00 / per week + taxes and fees
5
beds
4
Full,
1
Half Bath
sleeps
12
Pets Considered
No Events/Gatherings
Edgartown Chappaquiddick 421
This spacious 5 Bedroom home with a brand-new 20x60 saltwater pool and 8x12 hot tub is the ultimate Chappy getaway. Walk into the main level and you w... Read More
This spacious 5 Bedroom home with a brand-new 20x60 saltwater pool and 8x12 hot tub is the ultimate Chappy getaway. Walk into the main level and you w... Read More
June 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
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| 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 |
July 2026
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August 2026
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| 9 | 10 | 11 | 12 | 13 | 14 | $17,000 15 |
| 16 | 17 | 18 | 19 | 20 | 21 | $17,000 22 |
| 23 | 24 | 25 | 26 | 27 | 28 | $17,000 29 |
| 30 | 31 |
Available
Unavailable
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Experience the epitome of luxury and relaxation in this exquisite rental home. This meticulously designed retreat boasts high-end furnishings throughout, promising the utmost in comfort and style. Fully equipped, truly your home away from home. Outside is a private oasis, where an in-ground pool beckons you to unwind in the sun-drenched serenity of
$6,000.00 - $17,000.00 / per week + taxes and fees
4
beds
5
Full Bath
sleeps
8
Pets Not Allowed
No Events/Gatherings
Edgartown Downtown 2
Experience the epitome of luxury and relaxation in this exquisite rental home. This meticulously designed retreat boasts high-end furnishings througho... Read More
Experience the epitome of luxury and relaxation in this exquisite rental home. This meticulously designed retreat boasts high-end furnishings througho... Read More
June 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | $10,000 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | $12,000 13 |
| 14 | 15 | 16 | 17 | 18 | 19 | $15,000 20 |
| 21 | 22 | 23 | 24 | 25 | 26 | $17,000 27 |
| 28 | 29 | 30 |
July 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
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| 1 | 2 | 3 | $17,000 4 | |||
| 5 | 6 | 7 | 8 | 9 | 10 | $17,000 11 |
| 12 | 13 | 14 | 15 | 16 | 17 | $17,000 18 |
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August 2026
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| 16 | 17 | 18 | 19 | 20 | 21 | $15,000 22 |
| 23 | 24 | 25 | 26 | 27 | 28 | $15,000 29 |
| 30 | 31 |
Available
Unavailable
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Welcome to your Martha's Vineyard retreat in Edgartown! This stunning home, a testament to modern luxury, boasts new construction and is beautifully furnished throughout. Spacious and tastefully decorated living space, where the open-concept layout seamlessly connects the living room, dining area, and fully equipped kitchen, making it perfect for e
$18,000.00 - $27,000.00 / per week + taxes and fees
4
beds
3
Full,
1
Half Bath
sleeps
9
Pets Not Allowed
No Events/Gatherings
Edgartown Downtown 11
Welcome to your Martha's Vineyard retreat in Edgartown! This stunning home, a testament to modern luxury, boasts new construction and is beautifully f... Read More
Welcome to your Martha's Vineyard retreat in Edgartown! This stunning home, a testament to modern luxury, boasts new construction and is beautifully f... Read More
June 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 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 | $22,000 27 |
| 28 | 29 | 30 |
July 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
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| 1 | 2 | 3 | 4 | |||
| 5 | 6 | 7 | 8 | 9 | 10 | $22,000 11 |
| 12 | 13 | 14 | 15 | 16 | 17 | $22,000 18 |
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August 2026
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| 16 | 17 | 18 | 19 | 20 | 21 | $25,000 22 |
| 23 | 24 | 25 | 26 | 27 | 28 | $18,000 29 |
| 30 | 31 |
Available
Unavailable
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This exquisite residence boasts approximately 7,900 square feet of elegantly designed living space situated in an exceptional location. Encircled by Herring Creek Farm, the property offers exclusive access to a private dock and a secluded beach, providing a rare combination of seclusion and proximity to South Beach and Edgartown Village.
Within the
$45,000.00 - $65,000.00 / per week + taxes and fees
6
beds
7
Full,
2
Half Bath
sleeps
14
Pets Not Allowed
No Events/Gatherings
Edgartown Katama 524
This exquisite residence boasts approximately 7,900 square feet of elegantly designed living space situated in an exceptional location. Encircled by H... Read More
This exquisite residence boasts approximately 7,900 square feet of elegantly designed living space situated in an exceptional location. Encircled by H... Read More
June 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | $45,000 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | $45,000 13 |
| 14 | 15 | 16 | 17 | 18 | 19 | $45,000 20 |
| 21 | 22 | 23 | 24 | 25 | 26 | $55,000 27 |
| 28 | 29 | 30 |
July 2026
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| 1 | 2 | 3 | $55,000 4 | |||
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August 2026
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Available
Unavailable
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Nora's Lane is private, pristine and beautifully landscaped with a few ponds in a well thought out neighborhood setting. Fully air conditioned, five bedroom custom home is located just minutes from Edgartown village. This home includes a first floor primary en suite with walk in shower, double sinks and flat screen tv with doors out to the back dec
$9,000.00 - $27,750.00 / per week + taxes and fees
5
beds
6
Full Bath
sleeps
10
Pets Not Allowed
No Events/Gatherings
Edgartown Katama 528
Nora's Lane is private, pristine and beautifully landscaped with a few ponds in a well thought out neighborhood setting. Fully air conditioned, five b... Read More
Nora's Lane is private, pristine and beautifully landscaped with a few ponds in a well thought out neighborhood setting. Fully air conditioned, five b... Read More
June 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | $15,500 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | $25,500 13 |
| 14 | 15 | 16 | 17 | 18 | 19 | $26,500 20 |
| 21 | 22 | 23 | 24 | 25 | 26 | $27,000 27 |
| 28 | 29 | 30 |
July 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | $27,000 4 | |||
| 5 | 6 | 7 | 8 | 9 | 10 | $27,000 11 |
| 12 | 13 | 14 | 15 | 16 | 17 | $27,000 18 |
| 19 | 20 | 21 | 22 | 23 | 24 | $27,750 25 |
| 26 | 27 | 28 | 29 | 30 | 31 |
August 2026
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| 1 | ||||||
| 2 | 3 | 4 | 5 | 6 | 7 | 8 |
| 9 | 10 | 11 | 12 | 13 | 14 | 15 |
| 16 | 17 | 18 | 19 | 20 | 21 | $27,750 22 |
| 23 | 24 | 25 | 26 | 27 | 28 | $26,500 29 |
| 30 | 31 |
Available
Unavailable
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Check-Out
This vacation rental is a luxurious, in-town property located in the village of Edgartown. The home features four spacious bedrooms, several bathrooms, and multiple living areas, including a media room and two dens. The first floor includes a chef's kitchen, a dining room, a sitting room, and a porch with views of the backyard and pool. The primary
$15,000.00 - $25,000.00 / per week + taxes and fees
4
beds
4
Full,
1
Half Bath
sleeps
10
Pets Not Allowed
No Events/Gatherings
Edgartown Downtown 61
This vacation rental is a luxurious, in-town property located in the village of Edgartown. The home features four spacious bedrooms, several bathrooms... Read More
This vacation rental is a luxurious, in-town property located in the village of Edgartown. The home features four spacious bedrooms, several bathrooms... Read More
June 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | $18,000 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | $18,000 13 |
| 14 | 15 | 16 | 17 | 18 | 19 | $25,000 20 |
| 21 | 22 | 23 | 24 | 25 | 26 | 27 |
| 28 | 29 | 30 |
July 2026
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August 2026
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Available
Unavailable
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This private Main house abuts the backside of the third green of the nine hole Mink Meadows Golf Course in Vineyard Haven. The first floor includes a full den with a sleep sofa. TV's in all the bedrooms, living room, den and family room. The Guesthouse can be rented separately (please view rental code #1224 for more details). This property offers a
$6,500.00 - $8,500.00 / per week + taxes and fees
4
beds
3
Full,
1
Half Bath
sleeps
8
Pets Not Allowed
No Events/Gatherings
Vineyard Haven 1223
This private Main house abuts the backside of the third green of the nine hole Mink Meadows Golf Course in Vineyard Haven. The first floor includes a ... Read More
This private Main house abuts the backside of the third green of the nine hole Mink Meadows Golf Course in Vineyard Haven. The first floor includes a ... Read More
June 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | $6,500 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | $6,500 13 |
| 14 | 15 | 16 | 17 | 18 | 19 | $6,500 20 |
| 21 | 22 | 23 | 24 | 25 | 26 | $6,500 27 |
| 28 | 29 | 30 |
July 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | $7,800 4 | |||
| 5 | 6 | 7 | 8 | 9 | 10 | $7,800 11 |
| 12 | 13 | 14 | 15 | 16 | 17 | $7,800 18 |
| 19 | 20 | 21 | 22 | 23 | 24 | $7,800 25 |
| 26 | 27 | 28 | 29 | 30 | 31 |
August 2026
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| 16 | 17 | 18 | 19 | 20 | 21 | 22 |
| 23 | 24 | 25 | 26 | 27 | 28 | $8,500 29 |
| 30 | 31 |
Available
Unavailable
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Nestled on the tranquil bay side of Katama, this remarkable rental property stands as a true gem in the coastal landscape. A single-level architectural marvel bathes its interiors in an abundance of natural light, creating an inviting and spacious atmosphere. With two bedrooms boasting its own private bath, and two additional bunk rooms sharing the
$25,000.00 / per week + taxes and fees
4
beds
3
Full Bath
sleeps
8
Pets Not Allowed
No Events/Gatherings
Edgartown Katama 7028
Nestled on the tranquil bay side of Katama, this remarkable rental property stands as a true gem in the coastal landscape. A single-level architectura... Read More
Nestled on the tranquil bay side of Katama, this remarkable rental property stands as a true gem in the coastal landscape. A single-level architectura... 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 |
| 14 | 15 | 16 | 17 | 18 | 19 | $25,000 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 | $25,000 4 | |||
| 5 | 6 | 7 | 8 | 9 | 10 | $25,000 11 |
| 12 | 13 | 14 | 15 | 16 | 17 | $25,000 18 |
| 19 | 20 | 21 | 22 | 23 | 24 | $25,000 25 |
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August 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
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| 1 | ||||||
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| 16 | 17 | 18 | 19 | 20 | 21 | $25,000 22 |
| 23 | 24 | 25 | 26 | 27 | 28 | $25,000 29 |
| 30 | 31 |
Available
Unavailable
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Check-Out
Welcome to your perfect getaway on Martha's Vineyard! This beautifully decorated 3-bedroom, 2-bath home offers relaxation and convenience. Step outside and enjoy the heated saltwater pool, surrounded by comfortable lounge furniture - the ideal spot for soaking up the sun or unwinding in the evening. The floor plan is an open concept living, dining
$4,320.00 - $12,200.00 / per week + taxes and fees
3
beds
2
Full Bath
sleeps
10
Pets Considered
No Events/Gatherings
Edgartown 7823
Welcome to your perfect getaway on Martha's Vineyard! This beautifully decorated 3-bedroom, 2-bath home offers relaxation and convenience. Step outsid... Read More
Welcome to your perfect getaway on Martha's Vineyard! This beautifully decorated 3-bedroom, 2-bath home offers relaxation and convenience. Step outsid... Read More
June 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | $6,750 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | $7,000 13 |
| 14 | 15 | 16 | 17 | 18 | 19 | 20 |
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| 28 | 29 | 30 |
July 2026
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August 2026
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| 23 | 24 | 25 | 26 | 27 | 28 | $12,200 29 |
| 30 | 31 |
Available
Unavailable
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Relax in this nicely updated three-bedroom home located in the quiet neighborhood of Island Grove. The open-concept living room, dining area, and kitchen offer a comfortable and welcoming space for entertaining. The first floor includes a bedroom, an updated hall bath with laundry room. Upstairs, you'll find two spacious bedrooms that share a hall
$6,000.00 - $9,500.00 / per week + taxes and fees
3
beds
2
Full Bath
sleeps
6
Pets Considered
No Events/Gatherings
Edgartown 7825
Relax in this nicely updated three-bedroom home located in the quiet neighborhood of Island Grove. The open-concept living room, dining area, and kitc... Read More
Relax in this nicely updated three-bedroom home located in the quiet neighborhood of Island Grove. The open-concept living room, dining area, and kitc... Read More
June 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | $6,000 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | 13 |
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| 28 | 29 | 30 |
July 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
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| 1 | 2 | 3 | 4 | |||
| 5 | 6 | 7 | 8 | 9 | 10 | 11 |
| 12 | 13 | 14 | 15 | 16 | 17 | $8,700 18 |
| 19 | 20 | 21 | 22 | 23 | 24 | $8,700 25 |
| 26 | 27 | 28 | 29 | 30 | 31 |
August 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
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| 1 | ||||||
| 2 | 3 | 4 | 5 | 6 | 7 | 8 |
| 9 | 10 | 11 | 12 | 13 | 14 | $9,500 15 |
| 16 | 17 | 18 | 19 | 20 | 21 | 22 |
| 23 | 24 | 25 | 26 | 27 | 28 | $6,000 29 |
| 30 | 31 |
Available
Unavailable
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Approximately two miles from the heart of the Katama and South Beach areas. This beautifully designed and elegantly furnished six bedroom four and a half bathroom home is nestled in the Island Grove neighborhood where summer living is at its best. Lovely front curb appeal with cozy front porch, which wraps to the back spacious lawn where you will f
$5,500.00 - $18,500.00 / per week + taxes and fees
6
beds
4
Full,
1
Half Bath
sleeps
12
Pets Not Allowed
No Events/Gatherings
Edgartown Katama 7817
Approximately two miles from the heart of the Katama and South Beach areas. This beautifully designed and elegantly furnished six bedroom four and a h... Read More
Approximately two miles from the heart of the Katama and South Beach areas. This beautifully designed and elegantly furnished six bedroom four and a h... Read More
June 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | $10,000 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | 13 |
| 14 | 15 | 16 | 17 | 18 | 19 | $15,000 20 |
| 21 | 22 | 23 | 24 | 25 | 26 | $17,000 27 |
| 28 | 29 | 30 |
July 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | |||
| 5 | 6 | 7 | 8 | 9 | 10 | 11 |
| 12 | 13 | 14 | 15 | 16 | 17 | $17,500 18 |
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August 2026
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Available
Unavailable
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Vacation bliss awaits in this newer four-bedroom home with a pool in Chilmark. Enjoy the quiet luxury of up-island in this sophisticated contemporary retreat. Lounge by the pool, dine outdoors, and sleep peacefully in one of the Thuma beds. The main floor offers open-concept living, dining and kitchen spaces with grand vaulted ceilings anchored by
$15,000.00 - $20,000.00 / per week + taxes and fees
4
beds
3
Full,
1
Half Bath
sleeps
8
Pets Considered
No Events/Gatherings
Chilmark 2001
Vacation bliss awaits in this newer four-bedroom home with a pool in Chilmark. Enjoy the quiet luxury of up-island in this sophisticated contemporary ... Read More
Vacation bliss awaits in this newer four-bedroom home with a pool in Chilmark. Enjoy the quiet luxury of up-island in this sophisticated contemporary ... Read More
June 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 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 | $20,000 27 |
| 28 | 29 | 30 |
July 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | $20,000 4 | |||
| 5 | 6 | 7 | 8 | 9 | 10 | $20,000 11 |
| 12 | 13 | 14 | 15 | 16 | 17 | $20,000 18 |
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August 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | ||||||
| 2 | 3 | 4 | 5 | 6 | 7 | 8 |
| 9 | 10 | 11 | 12 | 13 | 14 | $20,000 15 |
| 16 | 17 | 18 | 19 | 20 | 21 | $18,000 22 |
| 23 | 24 | 25 | 26 | 27 | 28 | $15,000 29 |
| 30 | 31 |
Available
Unavailable
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Check-Out
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