Homes with Pools
your own pool. your own place
Martha's Vineyard already offers some of the most beautiful water you'll find anywhere on the Eastern Seaboard — but there's something uniquely indulgent about having a pool waiting for you the moment you step outside. No beach crowds, no timing swims around parking availability, no negotiating with the kids about when it's time to leave. Just your pool, your patio, your morning coffee beside it, and a vacation that unfolds entirely on your own terms.
Whatever size or style of home you're looking for, if a pool is on your list, this is where your search ends. For families with young children, it's a gamechanger. For groups of adults, it becomes the natural gathering place. For couples, it's simply one of the great quiet luxuries a vacation can offer.
Browse the full selection below.
142 properties available
Welcome to our exquisite vacation home in Katama! This contemporary home boasts 4 bedrooms, 2.5 baths, and sweeping views of the plains of Katama, and the distant ocean. Step onto the luxurious hardwood deck and indulge in the breathtaking scenery that surrounds you. The highlight of the property is the inviting pool area, perfect for relaxing and
Edgartown Katama 5011
Welcome to our exquisite vacation home in Katama! This contemporary home boasts 4 bedrooms, 2.5 baths, and sweeping views of the plains of Katama, and... Read More
Welcome to our exquisite vacation home in Katama! This contemporary home boasts 4 bedrooms, 2.5 baths, and sweeping views of the plains of Katama, and... Read More
No detail was overlooked in the design of this stunning five-bedroom home set on the hill. This home offers comfort and style and features rich countertops, stainless steel appliances, and an open floor plan that flows effortlessly between the kitchen, dining, and living areas. Three of the five bedrooms are en-suites, and the third-floor media and
Edgartown Downtown 123
No detail was overlooked in the design of this stunning five-bedroom home set on the hill. This home offers comfort and style and features rich counte... Read More
No detail was overlooked in the design of this stunning five-bedroom home set on the hill. This home offers comfort and style and features rich counte... Read More
Discover this stunning, rental home in the heart of Katama tucked away on a private street. Designed with comfort and style in mind, this spacious retreat offers ample room for friends and family to unwind, along with large gathering spaces perfect for shared moments. The main level boasts a vast, modern kitchen, dining area, living room, office, a
Edgartown Katama 610
Discover this stunning, rental home in the heart of Katama tucked away on a private street. Designed with comfort and style in mind, this spacious ret... Read More
Discover this stunning, rental home in the heart of Katama tucked away on a private street. Designed with comfort and style in mind, this spacious ret... Read More
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 gates of this pristine six-bedroom home. Spend the afternoon watching the horses while floating in the Salt treated pool or strolling along the nearby wildlife trails, then relax in the Salt treated ho
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
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
Stunning, newly constructed home with everything you could want for a carefree vacation! Located in downtown Edgartown's newest neighborhood, this home is a show stopper from top to bottom. The open floor plan features a large kitchen, dining area and living room with sliders spilling out to the patio and pool area. The first floor primary has a ba
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Edgartown Downtown 608
Stunning, newly constructed home with everything you could want for a carefree vacation! Located in downtown Edgartown's newest neighborhood, this hom... Read More
Stunning, newly constructed home with everything you could want for a carefree vacation! Located in downtown Edgartown's newest neighborhood, this hom... Read More
Edgartown Downtown 15
One of the most beautiful homes on North Water Street -- this seven bedroom historic Captain's Home, designed by Tracker Interiors, features multiple ... Read More
One of the most beautiful homes on North Water Street -- this seven bedroom historic Captain's Home, designed by Tracker Interiors, features multiple ... Read More
Stunning and immaculate 4500 square foot, 5 bedroom, custom Field Club home is waiting for your enjoyment. Inside you will find an open floor plan that extends the full length of the home. A large fully equipped chefs kitchen with a working island with access to ample seating, which spills to either indoor or outdoor dining just steps away. The f
Edgartown Katama 601
Stunning and immaculate 4500 square foot, 5 bedroom, custom Field Club home is waiting for your enjoyment. Inside you will find an open floor plan t... Read More
Stunning and immaculate 4500 square foot, 5 bedroom, custom Field Club home is waiting for your enjoyment. Inside you will find an open floor plan t... Read More
Meetinghouse Village end unit condo...This well appointed and adorable fully air conditioned contemporary condominium offers the privacy of an end unit, back deck for grilling and outdoor dining and an association in ground pool. Inside you will find a well equipped kitchen, lovely dining area which opens up to the spacious living area of comfy sof
Edgartown Condo 725
Meetinghouse Village end unit condo...This well appointed and adorable fully air conditioned contemporary condominium offers the privacy of an end uni... Read More
Meetinghouse Village end unit condo...This well appointed and adorable fully air conditioned contemporary condominium offers the privacy of an end uni... Read More
This private Main house abuts the backside of the third green of the nine hole Mink Meadows Golf Course in Vineyard Haven. The first floor includes a full den with a sleep sofa. TV's in all the bedrooms, living room, den and family room. The Guesthouse can be rented separately (please view rental code #1224 for more details). This property offers a
Vineyard Haven 1223
This private Main house abuts the backside of the third green of the nine hole Mink Meadows Golf Course in Vineyard Haven. The first floor includes a ... Read More
This private Main house abuts the backside of the third green of the nine hole Mink Meadows Golf Course in Vineyard Haven. The first floor includes a ... Read More
Designed by renowned architect Patrick Ahearn, this house offers a contemporary interpretation of a Martha's Vineyard Cape. Evoking the grandeur of an equestrian estate, this six-bedroom, nine-bath home is perched on a hill, overlooking a pond and situated on nearly four acres in the Preserve. The impeccably designed interiors create a sense of pla
Oak Bluffs 8168
Designed by renowned architect Patrick Ahearn, this house offers a contemporary interpretation of a Martha's Vineyard Cape. Evoking the grandeur of an... Read More
Designed by renowned architect Patrick Ahearn, this house offers a contemporary interpretation of a Martha's Vineyard Cape. Evoking the grandeur of an... Read More
Nestled amongst rolling spring lawns in a quiet, up-island setting sits a haven, echoing clean lines, meticulous design and comfort. This five bedroom with two en suite primarys, provides an abundance of sleeping room, with plenty of living spaces for family and friends to spread out. This home features a large kitchen with plenty of counter space
West Tisbury 100028
Nestled amongst rolling spring lawns in a quiet, up-island setting sits a haven, echoing clean lines, meticulous design and comfort. This five bedroom... Read More
Nestled amongst rolling spring lawns in a quiet, up-island setting sits a haven, echoing clean lines, meticulous design and comfort. This five bedroom... Read More
Tucked away on 20 acres along the shores of Vineyard Sound, Chip Chop is one of Martha's Vineyard's most iconic and storied properties. Originally built in the 1940s for Broadway star Katharine Cornell, this extraordinary beachfront compound has welcomed generations of notable guests from the worlds of theater, film, literature, and politics. Surro
Vineyard Haven 907
Tucked away on 20 acres along the shores of Vineyard Sound, Chip Chop is one of Martha's Vineyard's most iconic and storied properties. Originally bui... Read More
Tucked away on 20 acres along the shores of Vineyard Sound, Chip Chop is one of Martha's Vineyard's most iconic and storied properties. Originally bui... Read More
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