Vineyard Homes with Pools

MERRY

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Merry Farm Summer Estate, Heated Pool, Set on 28 Acres, Open Meadows, Private Retreat surrounded by Natural Beauty

Gorgeous, unique rental offering with heated pool, spectacular pastoral views across stone walls and acres of open fields bordered by mature oaks. The yard around the house is beautifully landscaped with...Read more

Location:

West Tisbury

Sleeps:

Bedrooms:

Bathrooms:

Price Range:

$9,000 - $15,000

Clean Fee:

$800 per week

Tax: State & Local:

11.7

Pool Heat July & August 82 to 84 degrees, included in rental rate

Pool Heat June & September 82 to 84 degrees, additional $300 per week

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CLAID

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Gorgeous New Contemporary Luxury Home, 18 x 38 Heated Pool, Hot Tub, Expansive Bluestone Patio, Beautiful Private Yard

Gorgeous new architect designed home featuring heated 18 x 30 - foot gunite pool with spacious bluestone patio, hot tub, 8 chaise lounge chairs and patio umbrellas. Additional patio area...Read more

Location:

Katama

Sleeps:

Bedrooms:

Bathrooms:

Price Range:

$9,500 - $21,500

Clean Fee:

$475 per week

Tax: State & Local:

9.7

2021 Pool Heated to 80 included in rental rate from 6/25 and ending 9/3

2021 Pool Heat all other weeks, temperatures vary and additional charges are set per the owner. Please inquire with agent for details and charges.

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SIMOA

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Exquisite New Luxury Home, Saltwater Pool 18 x 32 and Hot Tub, Ideally Situated in the Village Area, Walk to Shops, Dining and Harbor Area

Welcome to this gorgeous, and all newly renovated Edgartown Village area luxury home. This spacious home features expansive out-side entertainment area with heated saltwater pool, hot tub, large patio surround and deck with outdoor dining...Read more

Location:

Edgartown

Sleeps:

Bedrooms:

Bathrooms:

Price Range:

$10,000 - $20,000

Clean Fee:

$500

Tax: State & Local:

9.7

Pool is heated to 82 in July and August, included in rental rate. Pool heat June and September weeks, additional cost please inquire.

3 and 4 night Stays Available in May & after September 8th, Please inquire with agent!

Pool, Patios, Outdoor Dining, Patio Area with Firepit

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BRIGY

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Outstanding Designer Luxury Home, 18 X 30' Pool, Expansive Bluestone Patio with Outdoor Dining and Seating Areas

Oak Bluffs retreat featuring 18 X 30 foot pool, outdoor patio with sectional sofa seating, spacious dining deck and three levels of luxury living. The outstanding home has been professionally...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Bathrooms:

Price Range:

$6,500 - $12,500

Clean Fee:

$500 per week

Tax: State & Local:

11.7

Ferry Ticket available for week 7/28-8/4 (MV) - Please inquire

Pool heated to 81 degrees included in rental rate July & August, pool heated to 81 degrees June & September weeks additional $300 per week!

Hot Tub Heat, additional cost per week! Please inquire for details! Hot Tub heated by request only and owner operates remotley!

Yard, Pool, Patio, Deck and Outdoor Dining

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GORDM

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Gorgeous Contemporary Home, New Heated 20 x40 Pool for Summer 2016, New Furnishings for Summer 2016, Beautifully Landscaped in Most Desirable Deep Bottom, Association Tennis Courts, Shared Dock on Great Pond

Designed and built by one of the island premier firms and tucked in the exquisite community of homes known as Deep Bottom, this gracious home is sited on 2.78 acres with...Read more

Location:

West Tisbury

Sleeps:

Bedrooms:

Bathrooms:

Price Range:

$14,500 - $14,500

Clean Fee:

$500 per week

Tax: State & Local:

11.7

Pool Heated to 80 additional $250 per week first 2 weeks in September and $350 per week the last 2 weeks in September.

Pool, Hot Tub, Bluestone Pato, Dining and Grill area under Pergola

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CASTN

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Nora's Meadow, New Designer Home with Heated Gunite Pool and Hot Tub, Expansive Bluestone Patio, Screened Porch, 10 Minute Walk to Edgartown Village Center, Sleeps 14

Perfect for extended families,gorgeous new 5 bedroom, 4.5 bath luxury shore home, sleeps 14. This lovely home features a heated pool, patio area with pergola, hot tub and screened porch which overlooks...Read more

Location:

Edgartown

Sleeps:

Bedrooms:

Bathrooms:

Price Range:

$5,000 - $24,000

Clean Fee:

$850 per week

Tax: State & Local:

9.7

Owner has reduced rates on available weeks in 2020 - see calendar for adjusted rates.

Note: Pool heat and hot tub, heated to 81 degrees additional $350 per week

Request for Hot tub heated above 81 degrees in July and August, available upon request additional $325 weekly.

Note: Pool heat and hot tub shoulder season months: June, Sept and October to 81 degrees additional $350 per week. Hot tub heated to 98 upon request add an additional $350 per week. Combined cost $700

Pool, Patio, Back of House with Deck & Screened Porch

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GEORS

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Family Friendly Edgartown Home, Heated Pool, 12' x 25', Screened Porch, Deck, Ideally Located, 5 Minute Drive to South Beach and Edgartown Village, Tri Level home!

This lovley spacious home is Tucked away in Island Grove just on the outskirts of Edgarown Village. The outdoor living spaces include a heate pool with patio area, screened porch...Read more

Location:

Edgartown

Sleeps:

Bedrooms:

Bathrooms:

Price Range:

$6,500 - $9,000

Clean Fee:

$500 per week

Tax: State & Local:

9.7

Available weeks in July reduced by $1000 - see calendar for adjusted rates

Pool heated to 80 degrees, June through September included in rental rate!

Patio, Pool, Carriage House with Apartment 2nd Level, Lower Level Half Bath and Wet Bar

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CANNM

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Gorgeous Katama Family Compound with Pool, Ferry Tickets, Separate Carriage House Apartment

This beautiful, updated Katama home, with guest apartment over the carriage house, is perfect for extended families and made for beach lovers ( with South Beach just 5 minutes away) and pool...Read more

Location:

Katama

Sleeps:

Bedrooms:

Bathrooms:

Price Range:

$5,000 - $12,500

Clean Fee:

$400 per week

Tax: State & Local:

9.7

Pool Heat: Additional charge for pool heat to 82 degrees off season, June and September, $250 per week.

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LUCCA

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Newly Updated, Luxury Interior, Heated Pool, Screened Porch Overlooking Pool and Bluestone Patio

Set just on the outskirts of Edgartown Village and a short drive to South Beach this lovely home has been renovated top to bottom and features, new heated pool, a bluestone patio with chaise...Read more

Location:

Edgartown

Sleeps:

Bedrooms:

Bathrooms:

Price Range:

$6,500 - $14,000

Clean Fee:

$500 per week

Tax: State & Local:

9.7

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WEISM

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Outstanding Tri -Level Katama Home, Pool, new 18 x 40 Heated Saltwater Pool, Bluestone Patio, Fire PitWalk or Bike to South Beach and 5 minute Drive to Edgartown Village Area

Beautiful tri -level contemporary home will host an all new 18 x 40 heated saltwater pool with bluestone patio, outdoor dining area, chaise lounge chairs and fire pit. This recently updated home includes, spacious open...Read more

Location:

Katama

Sleeps:

Bedrooms:

Bathrooms:

Price Range:

$4,500 - $15,000

Clean Fee:

$500 per week

Tax: State & Local:

9.7

Pool is heated to 82 degrees July & August included. Pool heat June & September 82 degrees is an additional $350/week

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CARLP

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Distinctive Luxury All New For Summer 2016, Heated Pool 16 x 32, Village Center 3 Minute Walk to Main St.

Historic Edgartown Home fully renovated top to bottom for summer 2016. Perfect blend of restoration and renovation is seen throughout this stately home. Heated Pool 16 x 32' nearing completion, there...Read more

Location:

Edgartown

Sleeps:

Bedrooms:

Bathrooms:

Price Range:

$17,500 - $35,000

Clean Fee:

$700 per week

Tax: State & Local:

9.7

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CHUR2

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Designer Tri-Level Luxury Home with Heated Pool, Spacious Patio Area, Decks, Bike to South Beach, AC

Outstanding South Beach vacation home completely renovated in 2012. This custom crafted home has been professionally decorated. Walk or bike to South Beach approximately one half mile from the house....Read more

Location:

Katama

Sleeps:

Bedrooms:

Bathrooms:

Price Range:

$3,700 - $14,500

Clean Fee:

$350 per week

Tax: State & Local:

9.7

Owner reduced rate for week 6/27-7/4 by $1000 - see calendar for adjusted rate

Contemporary Home, Pool and Yard Area, Deck Overlooks Private yard and Pool

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BERNC

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Mini Retreat with Pool, Private Peaceful Chilmark Location, Lucy Vincent and Menemsha Beaches Nearby.

Impeccably maintained and updated this adorable summer home is perfect for families looking for luxury features such as quality linens in a quiet out of the way location. The 12...Read more

Location:

Chilmark

Sleeps:

Bedrooms:

Bathrooms:

Price Range:

$4,000 - $11,700

Clean Fee:

$375 per week

Tax: State & Local:

9.7

Pool Heat: June & Sept, pool heated to 82 degrees additional $250 for propane usage.

Pool, Patio, Harborfront Side of House, Enlarge the Photo to View the Pool

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RANSW

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Spectacular all new Harborfront Retreat, Heated Pool, Spacious Patio & Deck Areas, Stunning Views of Edgartown Harbor

Newly renovated, finely crafted, refined decor and luxury amenities. Spectacular waterviews across the decks, patio and pool to the Harbor from most of the living areas on the main level of this...Read more

Location:

Edgartown

Sleeps:

Bedrooms:

Bathrooms:

Price Range:

$20,000 - $51,000

Clean Fee:

$800 per week

Tax: State & Local:

9.7

2 week minimum stay in July & August

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TALLA