Homes with Pools

your own pool. your own place

Martha's Vineyard already offers some of the most beautiful water you'll find anywhere on the Eastern Seaboard — but there's something uniquely indulgent about having a pool waiting for you the moment you step outside. No beach crowds, no timing swims around parking availability, no negotiating with the kids about when it's time to leave. Just your pool, your patio, your morning coffee beside it, and a vacation that unfolds entirely on your own terms.

Whatever size or style of home you're looking for, if a pool is on your list, this is where your search ends. For families with young children, it's a gamechanger. For groups of adults, it becomes the natural gathering place. For couples, it's simply one of the great quiet luxuries a vacation can offer.

Browse the full selection below.

Properties Available 141 properties available
A taste of Chilmark in Edgartown - Stunning four-bedroom, 2 1/2 bath vacation home in the center of Edgartown Village, on a quiet cul-de-sac that is a 5-minute walk to restaurants and shops in downtown Edgartown. Listen to the bells ring from the Whaling Church, a quintessential part of the magic of downtown, yet with the space and privacy to rela
Hot HOT 17
Edgartown Downtown 42
Edgartown Downtown 42 2
Edgartown Downtown 42 3
Edgartown Downtown 42 4
Edgartown Downtown 42 5
Prev
Next
$20,000.00 - $24,000.00 / per week + taxes and fees
Beds 4 beds
Baths 2 Full, 1 Half Bath
Sleeps sleeps 8
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Downtown 42
A taste of Chilmark in Edgartown - Stunning four-bedroom, 2 1/2 bath vacation home in the center of Edgartown Village, on a quiet cul-de-sac that is ... Read More
June 2027
Su Mo Tu We Th Fr Sa
    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      
July 2027
Su Mo Tu We Th Fr Sa
        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 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $24,000 7
8 9 10 11 12 13 $24,000 14
15 16 17 18 19 20 $24,000 21
22 23 24 25 26 27 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out
Stunning Edgartown house with the wow factor! Located in Edgartown Village, this home is more than meets the eye. Completely re-mixed and updated for your fun and relaxing vacation. The bright contemporary decor has it all. The first floor has open-concept living, dining and a well-equipped kitchen. French doors bring you onto the patio and to the
Hot HOT 15
Edgartown Downtown 265
Edgartown Downtown 265 2
Edgartown Downtown 265 3
Edgartown Downtown 265 4
Edgartown Downtown 265 5
Prev
Next
$8,000.00 - $30,000.00 / per week + taxes and fees
Beds 4 beds
Baths 4 Full Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Downtown 265
Stunning Edgartown house with the wow factor! Located in Edgartown Village, this home is more than meets the eye. Completely re-mixed and updated for ... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $10,000 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      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 $20,000 17
18 19 20 21 22 23 $20,000 24
25 26 27 28 29 30 $25,000 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $30,000 7
8 9 10 11 12 13 $30,000 14
15 16 17 18 19 20 $25,000 21
22 23 24 25 26 27 $25,000 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out
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
Edgartown Katama 673
Edgartown Katama 673 2
Edgartown Katama 673 3
Edgartown Katama 673 4
Edgartown Katama 673 5
Prev
Next
$25,000.00 - $50,000.00 / per week + taxes and fees
Beds 5 beds
Baths 6 Full, 2 Half Bath
Sleeps sleeps 10
Pet Friendly Pets Considered
Not Pet Friendly 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
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $35,000 5
6 7 8 9 10 11 $35,000 12
13 14 15 16 17 18 $35,000 19
20 21 22 23 24 25 $50,000 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $50,000 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 $50,000 24
25 26 27 28 29 30 31
August 2027
Su Mo Tu We Th Fr Sa
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 $50,000 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out
 Discover the ultimate 5-bedroom retreat, where luxury and relaxation converge to redefine your vacation experience. This top-of-the-line, two-story home features central air, an inviting swimming pool, a sauna, cold plunge, and ocean views. Enjoy the spacious elegance and bright living spaces in the main house, featuring an en suite bedroom conven
Edgartown Chappaquiddick 300
Edgartown Chappaquiddick 300 2
Edgartown Chappaquiddick 300 3
Edgartown Chappaquiddick 300 4
Edgartown Chappaquiddick 300 5
Prev
Next
$5,000.00 - $23,000.00 / per week + taxes and fees
Beds 5 beds
Baths 5 Full, 1 Half Bath
Sleeps sleeps 9
Pet Friendly Pets Considered
Not Pet Friendly No Events/Gatherings
Edgartown Chappaquiddick 300
 Discover the ultimate 5-bedroom retreat, where luxury and relaxation converge to redefine your vacation experience. This top-of-the-line, two-story h... Read More
June 2027
Su Mo Tu We Th Fr Sa
    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      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 $21,000 17
18 19 20 21 22 23 $21,000 24
25 26 27 28 29 30 $21,000 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $23,000 7
8 9 10 11 12 13 $23,000 14
15 16 17 18 19 20 $23,000 21
22 23 24 25 26 27 $18,000 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out
Enjoy your summer vacation in this charming three-bedroom colonial-style home, featuring a relaxing in-ground heated pool. The property is located at the end of a quiet, dead-end street. Whether you head to the beach or enjoy a swim in your backyard, you'll have plenty of options for leisure. The home offers an ample dining room and deck space for
Edgartown 7767
Edgartown 7767 2
Edgartown 7767 3
Edgartown 7767 4
Edgartown 7767 5
Prev
Next
$7,000.00 - $12,000.00 / per week + taxes and fees
Beds 3 beds
Baths 3 Full, 1 Half Bath
Sleeps sleeps 8
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown 7767
Enjoy your summer vacation in this charming three-bedroom colonial-style home, featuring a relaxing in-ground heated pool. The property is located at ... Read More
June 2027
Su Mo Tu We Th Fr Sa
    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      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 $10,000 24
25 26 27 28 29 30 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 $12,000 21
22 23 24 25 26 27 $12,000 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out
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
Edgartown Katama 7817
Edgartown Katama 7817 2
Edgartown Katama 7817 3
Edgartown Katama 7817 4
Edgartown Katama 7817 5
Prev
Next
$5,500.00 - $18,750.00 / 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 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $10,250 5
6 7 8 9 10 11 $13,250 12
13 14 15 16 17 18 $15,500 19
20 21 22 23 24 25 $17,500 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $17,500 3
4 5 6 7 8 9 10
11 12 13 14 15 16 $18,000 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 $16,500 21
22 23 24 25 26 27 $12,000 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out
Experience this equestrian lover's dream home. This magnificent and meticulously maintained property features a spacious layout with an attached horse barn and an indoor riding arena. The heated pool is ideally situated between the primary residence and the barn, steps away from the house. The chef's kitchen comes equipped with all the modern ameni
West Tisbury 100055
West Tisbury 100055 2
West Tisbury 100055 3
West Tisbury 100055 4
West Tisbury 100055 5
Prev
Next
$14,000.00 / per week + taxes and fees
Beds 5 beds
Baths 4 Full, 1 Half Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
West Tisbury 100055
Experience this equestrian lover's dream home. This magnificent and meticulously maintained property features a spacious layout with an attached horse... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $14,000 5
6 7 8 9 10 11 $14,000 12
13 14 15 16 17 18 $14,000 19
20 21 22 23 24 25 $14,000 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $14,000 3
4 5 6 7 8 9 $14,000 10
11 12 13 14 15 16 $14,000 17
18 19 20 21 22 23 $14,000 24
25 26 27 28 29 30 $14,000 31
August 2027
Su Mo Tu We Th Fr Sa
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 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out
Large compound located in desirable Katama area and close to South Beach. The main house kitchen flows into a dining area with a large farm table. There is also a sun room, a living room and a TV room all located on the first floor. This spacious main house has seven bedrooms 5 bathrooms. Off the main living room is the entrance to the garage apart
Hot HOT 10
Edgartown Katama 511
Edgartown Katama 511 2
Edgartown Katama 511 3
Edgartown Katama 511 4
Edgartown Katama 511 5
Prev
Next
$9,500.00 - $24,000.00 / per week + taxes and fees
Beds 11 beds
Baths 7 Full Bath
Sleeps sleeps 20
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Katama 511
Large compound located in desirable Katama area and close to South Beach. The main house kitchen flows into a dining area with a large farm table. The... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $15,000 5
6 7 8 9 10 11 $15,000 12
13 14 15 16 17 18 $19,000 19
20 21 22 23 24 25 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        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 31
August 2027
Su Mo Tu We Th Fr Sa
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 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out
Martha's Vineyard gem. All you could want for Vineyard summer living. Beautifully appointed home with great indoor and outdoor spaces. This Down Harbor address offers an association beach and dock on beautiful Katama Bay, perfect for relaxing, sunning, swimming and fishing. In addition, the beach is ideal for launching a kayak or paddleboard and th
Edgartown Katama 7180
Edgartown Katama 7180 2
Edgartown Katama 7180 3
Edgartown Katama 7180 4
Edgartown Katama 7180 5
Prev
Next
$30,000.00 - $35,000.00 / per week + taxes and fees
Beds 5 beds
Baths 5 Full, 2 Half Bath
Sleeps sleeps 11
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Katama 7180
Martha's Vineyard gem. All you could want for Vineyard summer living. Beautifully appointed home with great indoor and outdoor spaces. This Down Harbo... Read More
June 2027
Su Mo Tu We Th Fr Sa
    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      
July 2027
Su Mo Tu We Th Fr Sa
        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 31
August 2027
Su Mo Tu We Th Fr Sa
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 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out
Welcome to this spacious four bedroom West Tisbury property with a private pool in a lovely community. This home is the perfect vacation destination for your family and friends. Walk in the front entry and you are greeted by an open grand space with high ceilings in the living area with the dining area and updated kitchen beyond. These spaces all
West Tisbury 100037
West Tisbury 100037 2
West Tisbury 100037 3
West Tisbury 100037 4
West Tisbury 100037 5
Prev
Next
$7,875.00 - $15,000.00 / per week + taxes and fees
Beds 4 beds
Baths 4 Full Bath
Sleeps sleeps 10
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
West Tisbury 100037
Welcome to this spacious four bedroom West Tisbury property with a private pool in a lovely community. This home is the perfect vacation destination f... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $8,500 5
6 7 8 9 10 11 $8,500 12
13 14 15 16 17 18 $10,000 19
20 21 22 23 24 25 $12,000 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $12,000 3
4 5 6 7 8 9 $12,000 10
11 12 13 14 15 16 $12,000 17
18 19 20 21 22 23 $12,000 24
25 26 27 28 29 30 $15,000 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $15,000 7
8 9 10 11 12 13 $15,000 14
15 16 17 18 19 20 $12,000 21
22 23 24 25 26 27 $12,000 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out
This Edgartown home is a dream come true for those seeking a luxurious island living experience. The expansive estate features six luxurious bedrooms, including two primary suites, one on each floor, with private en suite bathrooms. Two guest bedrooms with their own en suite baths offer added privacy, and two additional bedrooms share a well-appoin
Hot HOT 20
Edgartown 602
Edgartown 602 2
Edgartown 602 3
Edgartown 602 4
Edgartown 602 5
Prev
Next
$25,000.00 - $45,000.00 / per week + taxes and fees
Beds 6 beds
Baths 5 Full, 3 Half Bath
Sleeps sleeps 12
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown 602
This Edgartown home is a dream come true for those seeking a luxurious island living experience. The expansive estate features six luxurious bedrooms,... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $25,000 5
6 7 8 9 10 11 $30,000 12
13 14 15 16 17 18 $30,000 19
20 21 22 23 24 25 $41,500 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $41,500 3
4 5 6 7 8 9 $41,500 10
11 12 13 14 15 16 $41,500 17
18 19 20 21 22 23 $40,000 24
25 26 27 28 29 30 $45,000 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $45,000 7
8 9 10 11 12 13 $45,000 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out
Five-bedroom Cape centrally located in Oak Bluffs. The main house has been beautifully appointed, including an open kitchen, dining, and a living area with vaulted ceilings. The living area offers an oversized flat-screen TV and wood-burning fireplace leading into the Dining area, which opens up onto the back deck and pool area. The primary bedroo
Oak Bluffs 8116
Oak Bluffs 8116 2
Oak Bluffs 8116 3
Oak Bluffs 8116 4
Oak Bluffs 8116 5
Prev
Next
$9,100.00 - $20,000.00 / per week + taxes and fees
Beds 5 beds
Baths 4 Full Bath
Sleeps sleeps 14
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Oak Bluffs 8116
Five-bedroom Cape centrally located in Oak Bluffs. The main house has been beautifully appointed, including an open kitchen, dining, and a living area... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $9,100 5
6 7 8 9 10 11 $12,000 12
13 14 15 16 17 18 $16,500 19
20 21 22 23 24 25 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 3
4 5 6 7 8 9 $18,000 10
11 12 13 14 15 16 $19,000 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
August 2027
Su Mo Tu We Th Fr Sa
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 31        
Prev
Next
Available
Unavailable
Check-In
Check-Out

Tell us what you're looking for and someone will contact you with available options.

I agree