Martha's Vineyard Vacation Rentals - Homes with Pools
145 properties available
Just blocks to Edgartown Village! The compound includes main house, guest house and in ground pool, located on Clevelandtown Road. The main house offers 3 bedrooms including a primary bedroom with en suite bathroom, separate staircase, a beautifully flowing floorplan offers multiple casual and comfortable living spaces. A lovely front porch with co
$10,000.00 - $22,000.00 / per week + taxes and fees
4
beds
4
Full Bath
sleeps
10
Pets Not Allowed
No Events/Gatherings
Edgartown Downtown 142
Just blocks to Edgartown Village! The compound includes main house, guest house and in ground pool, located on Clevelandtown Road. The main house offe... Read More
Just blocks to Edgartown Village! The compound includes main house, guest house and in ground pool, located on Clevelandtown Road. The main house offe... Read More
June 2026
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| 1 | 2 | 3 | 4 | 5 | $11,000 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | $11,000 13 |
| 14 | 15 | 16 | 17 | 18 | 19 | $11,000 20 |
| 21 | 22 | 23 | 24 | 25 | 26 | $22,000 27 |
| 28 | 29 | 30 |
July 2026
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| 1 | 2 | 3 | $22,000 4 | |||
| 5 | 6 | 7 | 8 | 9 | 10 | $22,000 11 |
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August 2026
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| 16 | 17 | 18 | 19 | 20 | 21 | $22,000 22 |
| 23 | 24 | 25 | 26 | 27 | 28 | $12,500 29 |
| 30 | 31 |
Available
Unavailable
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A stunning home that exudes sophistication and a keen eye for design, this contemporary 5 bedroom, 4 bathroom home encompasses all of your vacations wants AND needs. The reverse floorplan has 3 bedrooms, two baths and a beautiful living space on the first floor, along with expansive windows and doors to beyond. The second floor unfolds in an open c
$10,000.00 - $30,000.00 / per week + taxes and fees
5
beds
4
Full,
1
Half Bath
sleeps
10
Pets Not Allowed
No Events/Gatherings
Edgartown Katama 5022
A stunning home that exudes sophistication and a keen eye for design, this contemporary 5 bedroom, 4 bathroom home encompasses all of your vacations w... Read More
A stunning home that exudes sophistication and a keen eye for design, this contemporary 5 bedroom, 4 bathroom home encompasses all of your vacations w... Read More
June 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
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| 1 | 2 | 3 | 4 | 5 | $15,000 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | $15,000 13 |
| 14 | 15 | 16 | 17 | 18 | 19 | $20,000 20 |
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July 2026
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August 2026
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Available
Unavailable
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A BRAND NEW, four-bedroom home that combines modern amenities with timeless style. Its prime location between downtown Edgartown and the beaches of Katama makes it the perfect place to enjoy all that the area has to offer. The custom entryway opens to a great room with a gas fireplace and cathedral ceilings, creating a warm and inviting space for r
$10,600.00 - $24,500.00 / per week + taxes and fees
4
beds
3
Full,
1
Half Bath
sleeps
10
Pets Not Allowed
No Events/Gatherings
Edgartown Katama 519
A BRAND NEW, four-bedroom home that combines modern amenities with timeless style. Its prime location between downtown Edgartown and the beaches of Ka... Read More
A BRAND NEW, four-bedroom home that combines modern amenities with timeless style. Its prime location between downtown Edgartown and the beaches of Ka... Read More
June 2026
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|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | 13 |
| 14 | 15 | 16 | 17 | 18 | 19 | $20,000 20 |
| 21 | 22 | 23 | 24 | 25 | 26 | $22,500 27 |
| 28 | 29 | 30 |
July 2026
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| 1 | 2 | 3 | 4 | |||
| 5 | 6 | 7 | 8 | 9 | 10 | 11 |
| 12 | 13 | 14 | 15 | 16 | 17 | $22,500 18 |
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| 26 | 27 | 28 | 29 | 30 | 31 |
August 2026
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| 23 | 24 | 25 | 26 | 27 | 28 | $15,100 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 charming Cape style property with 12' x 25' pool is perfect for making memories on your summer vacation. In the well-appointed kitchen, conveniently located just steps from the rear deck, everything you need to prepare meals, have a lobster boil or BBQ is at your fingertips. Dine on the deck overlooking the pool and well landscaped backyard.
$7,000.00 - $9,500.00 / per week + taxes and fees
3
beds
1
Full,
2
Half Bath
sleeps
8
Pets Not Allowed
No Events/Gatherings
Edgartown 746
This charming Cape style property with 12' x 25' pool is perfect for making memories on your summer vacation. In the well-appointed kitchen, convenie... Read More
This charming Cape style property with 12' x 25' pool is perfect for making memories on your summer vacation. In the well-appointed kitchen, convenie... Read More
June 2026
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| 1 | 2 | 3 | 4 | 5 | 6 | |
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| 21 | 22 | 23 | 24 | 25 | 26 | $7,000 27 |
| 28 | 29 | 30 |
July 2026
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| 5 | 6 | 7 | 8 | 9 | 10 | 11 |
| 12 | 13 | 14 | 15 | 16 | 17 | $8,000 18 |
| 19 | 20 | 21 | 22 | 23 | 24 | $8,000 25 |
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August 2026
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Available
Unavailable
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Nestled on a quiet street in the heart of Edgartown Village, this inviting four-bedroom home offers the perfect blend of comfort, privacy, and convenience. Featuring a 25x15 in-ground heated pool and spa, as well as generous off-street parking, this property is an ideal island retreat.
The thoughtfully designed open floor plan features a spacious p
$20,000.00 - $30,000.00 / per week + taxes and fees
6
beds
5
Full,
2
Half Bath
sleeps
12
Pets Not Allowed
No Events/Gatherings
Edgartown Downtown 145
Nestled on a quiet street in the heart of Edgartown Village, this inviting four-bedroom home offers the perfect blend of comfort, privacy, and conveni... Read More
Nestled on a quiet street in the heart of Edgartown Village, this inviting four-bedroom home offers the perfect blend of comfort, privacy, and conveni... Read More
June 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | $20,000 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | $20,000 13 |
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July 2026
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| 5 | 6 | 7 | 8 | 9 | 10 | $30,000 11 |
| 12 | 13 | 14 | 15 | 16 | 17 | $30,000 18 |
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August 2026
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| 16 | 17 | 18 | 19 | 20 | 21 | $28,000 22 |
| 23 | 24 | 25 | 26 | 27 | 28 | $28,000 29 |
| 30 | 31 |
Available
Unavailable
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Check-Out
Rambling meadow and a pond to view glorious sunsets while enjoying lots of outdoor space in West Tisbury. This centrally air conditioned custom home is located in a prestigious Deep Bottom neighborhood, with lots of privacy and lovely curb appeal. The queen guest bedroom is located on the first floor, while the King primary suite and other bedrooms
$13,000.00 - $15,000.00 / per week + taxes and fees
5
beds
3
Full Bath
sleeps
10
Pets Not Allowed
No Events/Gatherings
West Tisbury 1098
Rambling meadow and a pond to view glorious sunsets while enjoying lots of outdoor space in West Tisbury. This centrally air conditioned custom home i... Read More
Rambling meadow and a pond to view glorious sunsets while enjoying lots of outdoor space in West Tisbury. This centrally air conditioned custom home i... 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 | $15,000 22 |
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| 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 | 27 |
| 28 | 29 | 30 |
July 2026
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August 2026
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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 |
| 26 | 27 | 28 | 29 | 30 | 31 |
August 2026
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Available
Unavailable
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The perfect Katama home with every feature you could wish for in a rental property. This property offers ample room for living and lounging. Relax under an umbrella by the 800 Square foot heated pool. (Extra charge for pool heat in the off season). Grab a drink at the pool house while taking in a baseball game on the flat screen tv. Read a book in
$4,000.00 - $16,000.00 / per week + taxes and fees
6
beds
4
Full,
1
Half Bath
sleeps
14
Pets Not Allowed
No Events/Gatherings
Edgartown Katama 7188
The perfect Katama home with every feature you could wish for in a rental property. This property offers ample room for living and lounging. Relax und... Read More
The perfect Katama home with every feature you could wish for in a rental property. This property offers ample room for living and lounging. Relax und... Read More
June 2026
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|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | $8,000 6 | |
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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 | $16,000 29 |
| 30 | 31 |
Available
Unavailable
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Check-Out
As you head out of town down a private dirt road lined with glimpses of the ocean and sprawling lawns, you round a corner and find a house where the ocean envelopes you. The view from the driveway looks out to the front lawn, porch, patio, pool and ocean. A well-thought out design with an emphasis on private spaces, multiple living spaces both ind
$35,000.00 - $60,000.00 / per week + taxes and fees
7
beds
6
Full,
1
Half Bath
sleeps
10
Pets Not Allowed
No Events/Gatherings
Edgartown Downtown 109
As you head out of town down a private dirt road lined with glimpses of the ocean and sprawling lawns, you round a corner and find a house where the o... Read More
As you head out of town down a private dirt road lined with glimpses of the ocean and sprawling lawns, you round a corner and find a house where the o... Read More
June 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | 5 | $37,500 6 | |
| 7 | 8 | 9 | 10 | 11 | 12 | $37,500 13 |
| 14 | 15 | 16 | 17 | 18 | 19 | $37,500 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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Check-Out
Upon entering the prestigious Field Club development, you will be graced by an exquisitely designed home with a wonderful eye for detail. It is furnished with the finest linens, bedding, furniture and plenty of comfy sofas throughout. The first floor offers a long open floor plan beginning with a chefs dream kitchen of black granite counter tops
$20,000.00 - $40,000.00 / per week + taxes and fees
5
beds
4
Full Bath
sleeps
10
Pets Not Allowed
No Events/Gatherings
Edgartown Katama 7182
Upon entering the prestigious Field Club development, you will be graced by an exquisitely designed home with a wonderful eye for detail. It is furni... Read More
Upon entering the prestigious Field Club development, you will be graced by an exquisitely designed home with a wonderful eye for detail. It is furni... 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 | $40,000 27 |
| 28 | 29 | 30 |
July 2026
| Su | Mo | Tu | We | Th | Fr | Sa |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | $40,000 4 | |||
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| 19 | 20 | 21 | 22 | 23 | 24 | $40,000 25 |
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August 2026
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Available
Unavailable
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