Martha's Vineyard Vacation Rentals - Homes with Pools


Properties Available 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
Hot HOT 16
$12,000.00 - $17,000.00 / per week + taxes and fees
Beds 5 beds
Baths 4 Full, 1 Half Bath
Sleeps sleeps 12
Pet Friendly Pets Considered
Not Pet Friendly 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
June 2026
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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
Beds 4 beds
Baths 5 Full Bath
Sleeps sleeps 8
Not Pet Friendly Pets Not Allowed
Not Pet Friendly 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
June 2026
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  1 2 3 4 5 $10,000 6
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14 15 16 17 18 19 $15,000 20
21 22 23 24 25 26 $17,000 27
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July 2026
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August 2026
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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
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps sleeps 9
Not Pet Friendly Pets Not Allowed
Not Pet Friendly 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
June 2026
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  1 2 3 4 5 $18,500 6
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14 15 16 17 18 19 $18,500 20
21 22 23 24 25 26 $22,000 27
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July 2026
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5 6 7 8 9 10 $22,000 11
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August 2026
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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
Beds 6 beds
Baths 7 Full, 2 Half Bath
Sleeps sleeps 14
Not Pet Friendly Pets Not Allowed
Not Pet Friendly 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
June 2026
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  1 2 3 4 5 $45,000 6
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21 22 23 24 25 26 $55,000 27
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July 2026
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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
Hot HOT 20
$9,000.00 - $27,750.00 / per week + taxes and fees
Beds 5 beds
Baths 6 Full Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly 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
June 2026
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  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
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July 2026
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August 2026
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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
Beds 4 beds
Baths 4 Full, 1 Half Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly 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
June 2026
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  1 2 3 4 5 $18,000 6
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14 15 16 17 18 19 $25,000 20
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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
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps sleeps 8
Not Pet Friendly Pets Not Allowed
Not Pet Friendly 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
June 2026
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  1 2 3 4 5 $6,500 6
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July 2026
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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
Hot HOT 23
$25,000.00 / per week + taxes and fees
Beds 4 beds
Baths 3 Full Bath
Sleeps sleeps 8
Not Pet Friendly Pets Not Allowed
Not Pet Friendly 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
June 2026
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  1 2 3 4 5 $25,000 6
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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
Ferry Tickets Ferry Tickets
Ferry Tickets
July 5th - July 12th, August 2nd - August 9th
$4,320.00 - $12,200.00 / per week + taxes and fees
Beds 3 beds
Baths 2 Full Bath
Sleeps sleeps 10
Pet Friendly Pets Considered
Not Pet Friendly 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
June 2026
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  1 2 3 4 5 $6,750 6
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July 2026
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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
Beds 3 beds
Baths 2 Full Bath
Sleeps sleeps 6
Pet Friendly Pets Considered
Not Pet Friendly 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
June 2026
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July 2026
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August 2026
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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
Hot HOT 10
$5,500.00 - $18,500.00 / per week + taxes and fees
Beds 6 beds
Baths 4 Full, 1 Half Bath
Sleeps sleeps 12
Not Pet Friendly Pets Not Allowed
Not Pet Friendly 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
June 2026
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  1 2 3 4 5 $10,000 6
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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
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps sleeps 8
Pet Friendly Pets Considered
Not Pet Friendly 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
June 2026
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  1 2 3 4 5 $15,000 6
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July 2026
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23 24 25 26 27 28 $15,000 29
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