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

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discount tag Limited-Edition Luxury Short Stay

Introducing the Luxury Short Stay - A Rare Opportunity From Our Exclusive Vineyard Luxury Collection. Shorter 3 & 4-night escapes now available for May, June, and July. Unwind on your terms from midweek to long weekends. Email our rental team or give us a call 508.939.9422 

 

Luxe Katama Compound With Guest House, Pool And Spa $28,000 - $45,000/week

  • Property Highlights
    Unit Code: KAT RSTO-09C
    Pets Considered: Yes
    Town/Area: Edgartown - Katama
    • Bedrooms:6
    • Bath: 6.5
    • Sleeps:14
  • Description:
    POINT B EXCLUSIVE - This architect-designed Modern Farmhouse compound near South Beach, is tucked away in a quiet area... 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:
    **AUGUST SPECIAL: SAVE $2,500 Off 8/23 - 8/30 | NEW RATES PROGRAMMED IN** POINT B EXCLUSIVE - Located in a quiet... Read More
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Luxury In-Town Compound With Carriage House, Pool And Hot Tub $35,000 - $35,000/week

  • Property Highlights
    Unit Code: EDG DYAS-148
    Pets Considered: No
    Town/Area: Edgartown - Village
    • Bedrooms:6
    • Bath: 7.5
    • Sleeps:10
  • Description:
    POINT B EXCLUSIVE - Tucked away on Main Street at the top of Edgartown Village, this in-town luxury compound is designed... Read More
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Luxurious Compound In The Village With Pool And Pool House $10,000 - $35,000/week

100 Collection
  • 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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discount tag Limited-Edition Luxury Short Stay

Introducing the Luxury Short Stay - A Rare Opportunity From Our Exclusive Vineyard Luxury Collection. Shorter 3 & 4-night escapes now available for May, June, and July. Unwind on your terms from midweek to long weekends. Email our rental team or give us a call 508.939.9422 

 

Modern Farmhouse In Katama With Pool $20,000 - $35,000/week

  • Property Highlights
    Unit Code: KAT RSTO-09
    Pets Considered: No
    Town/Area: Edgartown - Katama
    • Bedrooms:4
    • Bath: 4.5
    • Sleeps:10
  • Description:
    POINT B EXCLUSIVE - This architect-designed Modern Farmhouse near South Beach, is tucked away in a quiet area of Katama... Read More
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discount tag Limited-Edition Luxury Short Stay

Introducing the Luxury Short Stay - A Rare Opportunity From Our Exclusive Vineyard Luxury Collection. Shorter 3 & 4-night escapes now available for May, June, and July. Unwind on your terms from midweek to long weekends. Email our rental team or give us a call 508.939.9422 

 

Elegant Country Estate With Pool In Katama $15,000 - $35,000/week

100 Collection
  • 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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Modern Farmhouse At Oyster Pond With Pool And Party Barn $14,000 - $32,025/week

100 Collection
  • 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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discount tag Limited-Edition Luxury Short Stay

Introducing the Luxury Short Stay - A Rare Opportunity From Our Exclusive Vineyard Luxury Collection. Shorter 3 & 4-night escapes now available for May, June, and July. Unwind on your terms from midweek to long weekends. Email our rental team or give us a call 508.939.9422 

 

In-Town Modern Colonial Compound With Pool $10,500 - $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:
    ** JULY+AUGUST SPECIAL: SAVE $3,000/WEEK OFF 6/27 - 7/4; 7/4 - 7/11; 8/22 - 8/29 | NEW RATES PROGRAMMED CALL TO BOOK **... Read More
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discount tag Limited-Edition Luxury Short Stay

Introducing the Luxury Short Stay - A Rare Opportunity From Our Exclusive Vineyard Luxury Collection. Shorter 3 & 4-night escapes now available for May, June, and July. Unwind on your terms from midweek to long weekends. Email our rental team or give us a call 508.939.9422 

 

Modern Farmhouse With Pool And Carriage House $7,000 - $30,000/week

100 Collection
  • 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 - Designed by noted architectural firm Hutker Architects, this modern interpretation of a classic... Read More
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discount tag Limited-Edition Luxury Short Stay

Introducing the Luxury Short Stay - A Rare Opportunity From Our Exclusive Vineyard Luxury Collection. Shorter 3 & 4-night escapes now available for May, June, and July. Unwind on your terms from midweek to long weekends. Email our rental team or give us a call 508.939.9422 

 

Luxurious Coastal-Style Living With Pool And Hot Tub In The Preserve $10,500 - $30,000/week

100 Collection
  • 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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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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