Martha's Vineyard Vacation Rentals - Homes with Pools

Properties Available 130 properties available
BR1 King En Suite with Separate Tub/Shower, Second FloorBR2 King, Second FloorHall Bath with Tub/Shower, Second FloorBR3 Queen En Suite with Shower Stall, Second FloorAdditional Sleeping (2) Twin Beds, LoftHall Bath with Tub/Shower, First FloorPowder Room, Lower LevelBR4 Queen En Suite with Half Bath, Second Floor Guest House
Edgartown 7772
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Edgartown 7772 3
Edgartown 7772 4
Edgartown 7772 5
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$20,000.00 - $32,000.00 / per week + taxes and fees
Beds 4 beds
Baths 4 Full, 2 Half Bath
Sleeps sleeps 10
Edgartown 7772
Immerse yourself in luxury and play at this gorgeous home - a multitude of living spaces, both indoor and outdoor, and the utmost in finishes inside, ... Read More
June 2025
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1 2 3 4 5 6 $27,500 7
8 9 10 11 12 13 $27,500 14
15 16 17 18 19 20 $27,500 21
22 23 24 25 26 27 $29,500 28
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July 2025
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    1 2 3 4 $29,500 5
6 7 8 9 10 11 $29,500 12
13 14 15 16 17 18 $32,000 19
20 21 22 23 24 25 $32,000 26
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August 2025
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24 25 26 27 28 29 $27,500 30
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BR1 Queen, Ensuite Bath with Combination Tub Shower, First FloorBR2 Queen Ensuite Bath with Soaking Tub, Shower, Double Vanity, Second FloorBR3 Pair of Twins with Trundle, Ensuite Bath with Combination Tub Shower, Second FloorBR4 Pair of Twin Over Twin Bunk Beds, Ensuite Bath with Combination Tub Shower, Second FloorBR5 Carriage House: Queen, Ensui
Edgartown Downtown 1
Edgartown Downtown 1 2
Edgartown Downtown 1 3
Edgartown Downtown 1 4
Edgartown Downtown 1 5
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$16,500.00 - $22,500.00 / per week + taxes and fees
Beds 5 beds
Baths 5 Full, 1 Half Bath
Sleeps sleeps 12
Edgartown Downtown 1
A charming Village home with separate guest accommodations and dipping pool set behind a white picket fence. The main house includes four bedrooms, al... Read More
June 2025
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1 2 3 4 5 6 $16,500 7
8 9 10 11 12 13 $16,500 14
15 16 17 18 19 20 $16,500 21
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July 2025
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August 2025
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24 25 26 27 28 29 $16,500 30
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BR1 King en suite with soaking tub and shower, First FloorBR2 King en suite with Shower, Second FloorBR3 Queen, Second FloorHall bath with tub/showerBR4 Queen en suite with shower, Second FloorHalf bath, First FloorLaundry area, First Floor
Edgartown Katama 722
Edgartown Katama 722 2
Edgartown Katama 722 3
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Edgartown Katama 722 5
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$12,000.00 - $25,000.00 / per week + taxes and fees
Beds 4 beds
Baths 5 Full, 1 Half Bath
Sleeps sleeps 8
Edgartown Katama 722
Picture yourself enjoying every luxurious detail of this gorgeous 4 bedroom home located approximately 1 mile from Downtown Edgartown. The first floor... Read More
June 2025
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1 2 3 4 5 6 $13,500 7
8 9 10 11 12 13 $15,100 14
15 16 17 18 19 20 $17,100 21
22 23 24 25 26 27 $22,000 28
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July 2025
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BR1 King En Suite with Shower Stall, First FloorBR2 King En Suite with Shower Stall, First FloorBR3 King & (2) Twin Beds in Loft En Suite with Shower Tub Combo (door to hallway), First FloorBR4 Bunk Bed (Twin/Twin), First FloorPowder Room, First FloorBR5 King En Suite with Shower Stall, Guest House
Hot HOT 37
West Tisbury 100051
West Tisbury 100051 2
West Tisbury 100051 3
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West Tisbury 100051 5
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$11,700.00 - $32,500.00 / per week + taxes and fees
Beds 5 beds
Baths 4 Full, 1 Half Bath
Sleeps sleeps 12
West Tisbury 100051
Nestled in a serene and secluded setting on the shore of Watcha Pond, this stunning 5-bedroom, 4.5-bathroom home spans 4,000 sq. ft. of luxurious livi... Read More
June 2025
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1 2 3 4 5 6 $16,300 7
8 9 10 11 12 13 $18,600 14
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July 2025
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    1 2 3 4 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 $32,500 26
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August 2025
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          1 $32,500 2
3 4 5 6 7 8 $32,500 9
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BR1 King En Suite with Shower Stall and Tub, First FloorBR2 Queen En Suite with Shower Stall and Tub, Second FloorBR3 Queen, Second FloorHall Bath with Shower Tub Combo, Second FloorBR4 (2) Twin Beds, Second FloorOverflow: Queen Sofabed, Den First FloorHall Bath with Shower Tub Combo, First Floor
Hot HOT 10
West Tisbury 100037
West Tisbury 100037 2
West Tisbury 100037 3
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West Tisbury 100037 5
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$7,875.00 - $13,335.00 / per week + taxes and fees
Beds 4 beds
Baths 4 Full Bath
Sleeps sleeps 10
West Tisbury 100037
Stunning four bedroom West Tisbury property with a private pool in a lovely community. This spacious home is the perfect vacation destination for you... Read More
June 2025
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July 2025
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    1 2 3 4 $12,000 5
6 7 8 9 10 11 $13,335 12
13 14 15 16 17 18 $13,335 19
20 21 22 23 24 25 $13,335 26
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August 2025
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10 11 12 13 14 15 $13,335 16
17 18 19 20 21 22 23
24 25 26 27 28 29 $8,000 30
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BR1 King En Suite with Shower Stall, First FloorBR2 Queen & Twin Bed En Suite with Shower Stall, Second FloorBR3 Queen En Suite with Shower Stall (only bedroom with no A/C ), Second FloorBR4 (2) Twin Beds, First FloorHall Bath with Shower Stall & Tub, First FloorPowder Room, Poolhouse
West Tisbury 100035
West Tisbury 100035 2
West Tisbury 100035 3
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$15,000.00 - $20,000.00 / per week + taxes and fees
Beds 4 beds
Baths 4 Full, 1 Half Bath
Sleeps sleeps 8
West Tisbury 100035
A spectacularly serene estate, contemporary design with Japanese influence, reflecting the surrounding landscape and accents from travels around the w... Read More
June 2025
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1 2 3 4 5 6 $15,000 7
8 9 10 11 12 13 $15,000 14
15 16 17 18 19 20 $15,000 21
22 23 24 25 26 27 $17,000 28
29 30          
July 2025
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    1 2 3 4 $20,000 5
6 7 8 9 10 11 $20,000 12
13 14 15 16 17 18 $20,000 19
20 21 22 23 24 25 $20,000 26
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August 2025
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          1 $20,000 2
3 4 5 6 7 8 $20,000 9
10 11 12 13 14 15 $20,000 16
17 18 19 20 21 22 $20,000 23
24 25 26 27 28 29 $20,000 30
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BR1 King en suite with separate tub and shower, 2nd floorBR2 (2)Twin beds en suite with tub/shower, 2nd floorHalf bath, 1st floorLaundry facilities, 1st floor
Hot HOT 10
Vineyard Haven 922
Vineyard Haven 922 2
Vineyard Haven 922 3
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$4,250.00 - $5,800.00 / per week + taxes and fees
Beds 2 beds
Baths 2 Full, 1 Half Bath
Sleeps sleeps 4
Vineyard Haven 922
Classic, custom built Tashmoo Cove two bedroom condo is located in a most sought after area of Vineyard Haven on Martha's Vineyard. This beautifully m... Read More
June 2025
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1 2 3 4 5 6 $4,250 7
8 9 10 11 12 13 $4,250 14
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Main House:BR1 King En Suite with Shower Stall and Tub, Second FloorBR2 King, Second FloorHall Bath with Shower Tub Combo, Second FloorBR3 King, Second FloorPrivate Staircase to BR4 King with walkthrough to BR5 (2) Twin Beds, Second FloorBR4 & BR5 Shared Bath with Shower Tub Combo, Second FloorGuest House:BR6 King En Suite with Shower Stall, Second
West Tisbury 100031
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West Tisbury 100031 3
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$15,000.00 - $25,000.00 / per week + taxes and fees
Beds 6 beds
Baths 5 Full, 1 Half Bath
Sleeps sleeps 14
West Tisbury 100031
Overlooking a seemingly endless meadow on over two and a half acres, you are at once overcome by tranquility and relaxation upon passing through the g... Read More
June 2025
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1 2 3 4 5 6 $25,000 7
8 9 10 11 12 13 $25,000 14
15 16 17 18 19 20 $25,000 21
22 23 24 25 26 27 $25,000 28
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July 2025
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    1 2 3 4 $25,000 5
6 7 8 9 10 11 $25,000 12
13 14 15 16 17 18 $25,000 19
20 21 22 23 24 25 $25,000 26
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August 2025
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BR1 Queen, 1st floor en suite with large shower BR2 King, second floor, en suite tub and showerBR3 Queen, 2nd floor BR 4 Two twins, 2nd floor BR 3 and BR 4, adjoining bathroom with shower
Hot HOT 10
Edgartown Downtown 2
Edgartown Downtown 2 2
Edgartown Downtown 2 3
Edgartown Downtown 2 4
Edgartown Downtown 2 5
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$5,000.00 - $17,000.00 / per week + taxes and fees
Beds 4 beds
Baths 5 Full Bath
Sleeps sleeps 8
Edgartown Downtown 2
Experience the epitome of luxury and relaxation in this exquisite, brand-new rental home. This meticulously designed retreat boasts high-end furnishin... Read More
June 2025
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1 2 3 4 5 6 $10,000 7
8 9 10 11 12 13 $12,000 14
15 16 17 18 19 20 $15,000 21
22 23 24 25 26 27 $17,000 28
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July 2025
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6 7 8 9 10 11 $17,000 12
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August 2025
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17 18 19 20 21 22 $15,000 23
24 25 26 27 28 29 $15,000 30
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BR1 Queen, en suite, first floor BR2 King, en suite, second floor BR3 King, en suite, second floor BR4 Queen and Twin bunk, en suite BR5 King, en suite.
Edgartown Chappaquiddick 300
Edgartown Chappaquiddick 300 2
Edgartown Chappaquiddick 300 3
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Pet Friendly
$5,000.00 - $23,000.00 / per week + taxes and fees
Beds 5 beds
Baths 5 Full, 1 Half Bath
Sleeps sleeps 9
Edgartown Chappaquiddick 300
Discover the ultimate 5-bedroom, 9-sleeper retreat on Chappaquiddick Island, Martha's Vineyard, where luxury and relaxation converge to redefine your ... Read More
June 2025
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1 2 3 4 5 6 $8,000 7
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July 2025
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24 25 26 27 28 29 $12,000 30
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BR1 Queen En Suite with Shower Stall, First FloorBR2 King, 2nd floorBR3 Queen, 2nd floorHall bath with tub and shower, 2nd floorBR4 (2) doubles, lower levelHall Bath with Shower Stall, Lower Level
Vineyard Haven 965
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Vineyard Haven 965 3
Vineyard Haven 965 4
Vineyard Haven 965 5
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$12,000.00 - $18,000.00 / per week + taxes and fees
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps sleeps 10
Vineyard Haven 965
Experience this modern and contemporary home nestled in a private setting off Lambert's Cove Road. Spread out on 3 levels, this home has modern amenit... Read More
June 2025
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $12,000 7
8 9 10 11 12 13 $12,000 14
15 16 17 18 19 20 $16,000 21
22 23 24 25 26 27 $16,000 28
29 30          
July 2025
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    1 2 3 4 $16,000 5
6 7 8 9 10 11 $16,000 12
13 14 15 16 17 18 $16,000 19
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August 2025
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17 18 19 20 21 22 $18,000 23
24 25 26 27 28 29 $16,000 30
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BR1 King en suite with soaking tub and shower, 1st floorBR2 King en suite with shower stall, 2nd floorBR3 Queen en suite with shower, 2nd floorBR4 Double with trundle en suite with tub/shower, 2nd floorBR5 (2)Bunk beds and double bed en suite with shower stall, lower levelHall bath, lower levelBR6 (2)Bunk beds and double bed en suite with shower st
Hot HOT 22
Oak Bluffs 8168
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Oak Bluffs 8168 3
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Oak Bluffs 8168 5
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$17,500.00 - $34,000.00 / per week + taxes and fees
Beds 6 beds
Baths 9 Full Bath
Sleeps sleeps 16
Oak Bluffs 8168
Designed by renowned architect Patrick Ahearn, this house is meant to be a contemporary interpretation of a Martha's Vineyard Cape. Evoking the grand... Read More
June 2025
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1 2 3 4 5 6 $25,000 7
8 9 10 11 12 13 $25,000 14
15 16 17 18 19 20 $27,500 21
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