Martha's Vineyard Vacation Rentals with Pools

Book your spacious and private Martha's Vineyard vacation rental with a pool. These homes have everything you need for a stress-free vacation with one of the best amenities - a pool! Contact Point B Realty to help you find the perfect Martha's Vineyard Rental for your next trip.  You can also view all of our incredible Martha's Vineyard vacation rentals.

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116 properties returned | Your Current Search: Pool Features: Pools

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Casa Katama: Luxury Compound With Guest House And Pool $35,000 - $40,000/week

  • Property Highlights
    Unit Code: KAT KWEI-24
    Pets Considered: Yes
    Town/Area: Edgartown - Katama
    • Bedrooms:6
    • Bath:8.5
    • Sleeps:16
  • Description:
    POINT B EXCLUSIVE - This stunning Katama compound features a Main House with three levels of uniquely designed green... Read More
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Stunning Katama Compound With Pool, Hot Tub And Private Beach $35,000 - $40,000/week

  • Property Highlights
    Unit Code: KAT LCRI-22
    Pets Considered: No
    Town/Area: Edgartown - Katama
    • Bedrooms:6
    • Bath:5.5
    • Sleeps:12
  • Description:
    POINT B EXCLUSIVE - Quietly tucked away on a knoll just above Katama Bay, this stunning Modern Farmhouse Compound is... Read More
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Grand Edgartown Village Compound With Pool $10,000 - $35,000/week

  • Property Highlights
    Unit Code: EDG TMOR-27
    Pets Considered: No
    Town/Area: Edgartown - Village
    • Bedrooms:6
    • Bath:6.5
    • Sleeps:16
  • Description:
    POINT B EXCLUSIVE - Located in a quiet neighborhood on the edge of Edgartown Village, this newly built Grand Colonial... Read More
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Luxurious Compound In The Village With Pool And Pool House $10,000 - $35,000/week

  • Property Highlights
    Unit Code: EDG CBRI-12
    Pets Considered: No
    Town/Area: Edgartown - Village
    • Bedrooms:6
    • Bath:6.5
    • Sleeps:12
  • Description:
    POINT B EXCLUSIVE - Designed by noted architect Patrick Ahearn, this grand in-town compound features deluxe... Read More
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Elegant Country Estate With Pool In Katama $15,000 - $35,000/week

  • Property Highlights
    Unit Code: KAT CCAS-29
    Pets Considered: No
    Town/Area: Edgartown - Katama
    • Bedrooms:4
    • Bath:4.5
    • Sleeps:12
  • Description:
    POINT B EXCLUSIVE - Sited at the end of a long private drive, amid a bucolic 1.5-acre meadow setting with stone... Read More
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discount tag Peak Weeks Available For August 2025


Some of the biggest events of the summer on Martha's Vineyard are moving a week later next year. The Agricultural Fair, Illumination Night, and the Oak Bluffs Fireworks are ALL moving to the third week of August in 2025 (August 15 - 24). This past summer, all those peak week events occured during the second week. Given the popularity of that week, lots of Martha's Vineyard vacation rentals are booked by repeat renters or get rented quickly. Good news, we've got a great collection of luxury homes that are available for next August. You can browse the collection here or call our Rental Team to explore your options 508.939.9422

Modern Farmhouse At Oyster Pond With Pool And Party Barn $10,000 - $32,500/week

  • Property Highlights
    Unit Code: EDG WBAK-80
    Pets Considered: No
    Town/Area: Edgartown - Other
    • Bedrooms:5
    • Bath:4.5
    • Sleeps:10
  • Description:
    POINT B EXCLUSIVE - Quietly set back on four private acres in the prestigious Oyster Pond area of Edgartown, this... Read More
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In-Town Modern Colonial Compound With Pool $8,500 - $30,000/week

  • Property Highlights
    Unit Code: EDG CCAS-31
    Pets Considered: No
    Town/Area: Edgartown - Village
    • Bedrooms:5
    • Bath:5.5
    • Sleeps:14
  • Description:
    POINT B EXCLUSIVE - This luxurious in-town Modern Colonial with pool, is designed for indoor-outdoor living, with lots... Read More
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Grand Coastal-Style Estate In The Preserve With Pool And Hot Tub $10,000 - $30,000/week

  • Property Highlights
    Unit Code: OB RSMI-16
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:5
    • Bath:6.5
    • Sleeps:12
  • Description:
    POINT B EXCLUSIVE - This recently built luxury home features three floors of deluxe indoor living space, with nicely... Read More
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discount tag Peak Weeks Available For August 2025


Some of the biggest events of the summer on Martha's Vineyard are moving a week later next year. The Agricultural Fair, Illumination Night, and the Oak Bluffs Fireworks are ALL moving to the third week of August in 2025 (August 15 - 24). This past summer, all those peak week events occured during the second week. Given the popularity of that week, lots of Martha's Vineyard vacation rentals are booked by repeat renters or get rented quickly. Good news, we've got a great collection of luxury homes that are available for next August. You can browse the collection here or call our Rental Team to explore your options 508.939.9422

Katama Compound With Pool, Pool House, Pickleball + Tennis Court $15,000 - $30,000/week

  • Property Highlights
    Unit Code: KAT KODO-11
    Pets Considered: No
    Town/Area: Edgartown - Katama
    • Bedrooms:4
    • Bath:3.5
    • Sleeps:9
  • Description:
    POINT B EXCLUSIVE - This luxurious Katama Compound has undergone a complete reimagining of and renovation throughout the... Read More
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Modern Farmhouse With Pool And Carriage House $7,500 - $28,000/week

  • Property Highlights
    Unit Code: KAT MALI-05
    Pets Considered: No
    Town/Area: Edgartown - Katama
    • Bedrooms:5
    • Bath:5.5
    • Sleeps:10
  • Description:
    POINT B EXCLUSIVE - *Special Offer: Save 25-30% on September Weeks* (new rates programmed). Designed by noted... Read More
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discount tag Peak Weeks Available For August 2025


Some of the biggest events of the summer on Martha's Vineyard are moving a week later next year. The Agricultural Fair, Illumination Night, and the Oak Bluffs Fireworks are ALL moving to the third week of August in 2025 (August 15 - 24). This past summer, all those peak week events occured during the second week. Given the popularity of that week, lots of Martha's Vineyard vacation rentals are booked by repeat renters or get rented quickly. Good news, we've got a great collection of luxury homes that are available for next August. You can browse the collection here or call our Rental Team to explore your options 508.939.9422

Luxurious New Gambrel With Pool $10,000 - $28,000/week

  • Property Highlights
    Unit Code: EDG JROG-16
    Pets Considered: No
    Town/Area: Edgartown - Village
    • Bedrooms:4
    • Bath:4.5
    • Sleeps:10
  • Description:
    POINT B EXCLUSIVE - This luxurious architect-designed Gambrel is made for indoor-outdoor island living, with great... Read More
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Sleek Modern Farmhouse In Katama With Pool $15,000 - $28,000/week

  • Property Highlights
    Unit Code: KAT MCHA-37
    Pets Considered: No
    Town/Area: Edgartown - Katama
    • Bedrooms:5
    • Bath:4.5
    • Sleeps:12
  • Description:
    POINT B EXCLUSIVE - This recently built Modern Farmhouse is located in a quiet central Katma neighborhood. It features... Read More
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