Martha's Vineyard Vacation Rentals - Homes with Pools

Properties Available 131 properties available
BR1 King En Suite with Shower Stall & Tub, First FloorBR2 King En Suite with Shower Stall & Tub, Second Floor BR3 King En Suite with Shower Stall, Second FloorBR4 Queen En Suite with Shower Stall, Second FloorBR5 Queen En Suite with Tub Shower Combo, Second FloorPowder Room, First FloorPowder Room, Poolhouse
Oak Bluffs 826
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Pet Friendly
$15,000.00 - $30,000.00 / per week + taxes and fees
Beds 5 beds
Baths 5 Full, 1 Half Bath
Sleeps 10 sleeps
Oak Bluffs 826
The Preserve off of County Road boasts luxurious accommodations with five modern air-conditioned bedrooms, each with an en-suite bathroom. The first-f... Read More
June 2025
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July 2025
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    1 2 3 4 $24000 5
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BR1 King en suite soaking tub and shower & private deck,, 2nd floorBR2 King en suite with shower, 2nd floorBR3 Queen en suite shower, 2nd floorBR4 Queen en suite shower, 2nd floorAdditional: (2)Twin beds, 3rd floor loftHall bath tub/shower, 3rd floor loftHalf bath, 1st floorHall bath with shower, lower level
Edgartown Downtown 45
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$27,000.00 - $29,500.00 / per week + taxes and fees
Beds 4 beds
Baths 6 Full, 1 Half Bath
Sleeps 10 sleeps
Edgartown Downtown 45
In town Edgartown on the west side of Cooke Street, this four bedroom, all en suite with a loft area for extra sleeping, is exquisitely designed and t... Read More
June 2025
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1 2 3 4 5 6 $27000 7
8 9 10 11 12 13 $27000 14
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10 11 12 13 14 15 $29500 16
17 18 19 20 21 22 $29500 23
24 25 26 27 28 29 $29500 30
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BR1 King Bedroom, en-suite, with attached sitting are with a flat-screen TV. Main floor BR2 Queen Bedroom, en-suite, flat-screen TV, Second Floor BR3 Queen Bedroom, en-suite, Second Floor BR4 (2)Twins, en-suite, Second Floor Additional Sleeping alcove with a Twin Day bed, Second Floor
Edgartown 591
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$15,000.00 - $30,000.00 / per week + taxes and fees
Beds 4 beds
Baths 5 Full Bath
Sleeps 9 sleeps
Edgartown 591
Imagine indulging in luxury in this stunning four-bedroom Katama home, located about a mile away from downtown Edgartown and two miles from South Beac... Read More
June 2025
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1 2 3 4 5 6 $20000 7
8 9 10 11 12 13 $20000 14
15 16 17 18 19 20 $20000 21
22 23 24 25 26 27 $22000 28
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July 2025
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    1 2 3 4 $22000 5
6 7 8 9 10 11 $25000 12
13 14 15 16 17 18 $25000 19
20 21 22 23 24 25 $30000 26
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10 11 12 13 14 15 $30000 16
17 18 19 20 21 22 $25000 23
24 25 26 27 28 29 $20000 30
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Main house:BR1 King en suite with tub and shower, 2nd floorBR2 Queen, 2nd floorBR3 Queen, 2nd floorJack & Jill bath with shower, 2nd floor (shared by BR2 & BR3)BR4 Queen, 2nd floorBR5 Queen, 2nd floorJack & Jill bath tub/shower, 2nd floor (shared by BR4 & BR5)Hall bath with shower, lower levelHalf bath, 1st floorGuesthouse above garage:BR6 Queen an
Edgartown Downtown 3
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$50,000.00 / per week + taxes and fees
Beds 7 beds
Baths 5 Full, 1 Half Bath
Sleeps 12 sleeps
Edgartown Downtown 3
Luxuriously stunning downtown Edgartown home with lovely views of the Sound on one side and poolside on the other. All you could want or need for a M... Read More
June 2025
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1 2 3 4 5 6 $50000 7
8 9 10 11 12 13 $50000 14
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July 2025
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BR1 King En Suite with Shower Stall & Tub, First FloorBR2 King & (2) Twin Beds En Suite with Shower Stall & Tub, Second FloorBR3 King En Suite with Shower Stall, Second FloorBR4 Queen En Suite, Second FloorBR5 Queen En Suite with Shower Stall, Lower Level (2) Powder Rooms, First FloorBR6 Queen, Guest HouseHall Bath with Shower Stall, Guest HousePow
Edgartown 7754
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$55,000.00 - $75,000.00 / per week + taxes and fees
Beds 6 beds
Baths 6 Full, 1 Half Bath
Sleeps 14 sleeps
Edgartown 7754
Built by one of the premier builders of Martha's Vineyard, this 10,000 square foot property sits upon a bluff overlooking Sengekontacket Pond and Nan... Read More
June 2025
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1 2 3 4 5 6 $60000 7
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15 16 17 18 19 20 $60000 21
22 23 24 25 26 27 $75000 28
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    1 2 3 4 $60000 5
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13 14 15 16 17 18 $75000 19
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          1 $75000 2
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17 18 19 20 21 22 $60000 23
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Full bath of shower tub combo on first floorAll bedrooms located on the 2nd floor with the exception of the Pool HouseBR1 King second floor, en suite (separate staircase)BR2 Double and two twins, 2nd floorBR3 Queen, 2nd floor, hall bath of shower, 2nd floor shared between BR 2 and BR 3BR4 Queen, Pool House, full bath of showerNote, full bath on fir
Hot HOT 34
Edgartown Downtown 142
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$10,000.00 - $22,000.00 / per week + taxes and fees
Beds 4 beds
Baths 4 Full Bath
Sleeps 10 sleeps
Edgartown Downtown 142
Just blocks to Edgartown Village! The compound includes main house, guest house and in ground pool, located on Clevelandtown Road. Newly renovated an... Read More
June 2025
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1 2 3 4 5 6 $11000 7
8 9 10 11 12 13 $11000 14
15 16 17 18 19 20 $11000 21
22 23 24 25 26 27 $22000 28
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July 2025
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    1 2 3 4 $22000 5
6 7 8 9 10 11 $22000 12
13 14 15 16 17 18 $22000 19
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3 4 5 6 7 8 $22000 9
10 11 12 13 14 15 $22000 16
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24 25 26 27 28 29 $12500 30
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BD1: King with Television, First Floor. BD2: Pair of Twins (XL), First Floor. First Floor. BD3: Queen Bed, Twin Over Twin Bunk Beds, Television, First Floor. BD4: King, Ensuite Bath, Television, Second Floor. BD5 (Over Garage): King with Private Bath with Shower.
Edgartown Katama 5022
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$10,000.00 - $30,000.00 / per week + taxes and fees
Beds 5 beds
Baths 4 Full, 1 Half Bath
Sleeps 10 sleeps
Edgartown Katama 5022
A stunning renovation that exudes sophistication and a keen eye for design, this contemporary 5 bedroom, 4 bathroom home encompasses all of your vacat... Read More
June 2025
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1 2 3 4 5 6 $15000 7
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13 14 15 16 17 18 $28500 19
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BR1 King en suite with separate tub and shower, 1st floorBR2 King en suite with shower, 2nd floorBR3 (2)Twin beds, 2nd floorBR4 (2)Twin beds, 2nd floorHall bath with tub/shower, 2nd floorLaundry facilities, 1st floorHalf bath, 1st floor
Oak Bluffs 8141
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$12,000.00 - $22,000.00 / per week + taxes and fees
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps 8 sleeps
Oak Bluffs 8141
Don't miss out on this amazing vacation opportunity on Martha's Vineyard! You can relax in the comfortable living room and enjoy the beautiful view th... Read More
June 2025
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1 2 3 4 5 6 $12000 7
8 9 10 11 12 13 $12000 14
15 16 17 18 19 20 $12500 21
22 23 24 25 26 27 $16000 28
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July 2025
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    1 2 3 4 $16000 5
6 7 8 9 10 11 $16500 12
13 14 15 16 17 18 $17500 19
20 21 22 23 24 25 $22000 26
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24 25 26 27 28 29 $16000 30
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BR1 Queen en suite with separate tub and shower, 2nd floorBR2 King, 3rd floorHall bath with separate tub and shower, 3rd floorBR3 Double, 1st floorBR4 Double, 1st floorHall bath with tub/shower, 1st floorGuest house: BR5 Queen, 2nd floorHall bath with tub/shower, 1st floor
Oak Bluffs 878
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$8,000.00 - $20,000.00 / per week + taxes and fees
Beds 5 beds
Baths 5 Full Bath
Sleeps 10 sleeps
Oak Bluffs 878
Sprawling family compound tucked into the woods of Oak Bluffs. Entering into this beautifully landscaped property, the split rail fencing leads past t... Read More
June 2025
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1 2 3 4 5 6 $16000 7
8 9 10 11 12 13 $16000 14
15 16 17 18 19 20 $16000 21
22 23 24 25 26 27 $20000 28
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July 2025
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    1 2 3 4 $20000 5
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13 14 15 16 17 18 $20000 19
20 21 22 23 24 25 $20000 26
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24 25 26 27 28 29 $8000 30
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BR1 King en suite tub/shower, 1st floor BR2 Queen, 1st floorHall bath tub/shower, 1st floorBR3 King, 2nd floorBR4 (2)Twin beds & Daybed, 2nd floor(Daybed tucked in large closet)Hall bath tub/shower, 2nd floorHalf bath & laundry, 1st floor
West Tisbury 1112
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Pet Friendly
$12,000.00 - $14,000.00 / per week + taxes and fees
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps 8 sleeps
West Tisbury 1112
Lovely pool and private setting off of Indian Hill Road in West Tisbury. Enjoy summer days in this spacious four bedroom home with a great front farm... Read More
June 2025
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17 18 19 20 21 22 $12000 23
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BR1 Queen En Suite with Shower Stall, First FloorBR2 Queen, First FloorHall Bath with Shower Stall, First FloorBR3 (2) Twin Beds, First FloorQueen Sleeper Sofa in Den
Edgartown Downtown 81
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$6,500.00 - $13,575.00 / per week + taxes and fees
Beds 3 beds
Baths 2 Full Bath
Sleeps 8 sleeps
Edgartown Downtown 81
Recently renovated, this three-bedroom single-story bungalow is centrally located in Edgartown. The dining area opens up to an outdoor living space wi... Read More
June 2025
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1 2 3 4 5 6 $6500 7
8 9 10 11 12 13 $7500 14
15 16 17 18 19 20 $8500 21
22 23 24 25 26 27 $10000 28
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BR1 King En suite with Soaking Tub and Shower, First FloorBR2 Queen En suite with Shower Stall, First FloorBR3 Queen En suite with Shower Stall, First FloorBR4 Queen En suite with Shower Stall, First Floor
Oak Bluffs 8134
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$23,000.00 - $24,000.00 / per week + taxes and fees
Beds 4 beds
Baths 5 Full, 1 Half Bath
Sleeps 8 sleeps
Oak Bluffs 8134
A stunning four-bedroom home in one of the prestigious "Preserve" neighborhood in Oak Bluffs - perched on a hill overlooking the pond, the sprawling ... Read More
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