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.
143 properties available
Don't miss out on this amazing vacation opportunity on Martha's Vineyard! You can relax in the comfortable living room and enjoy the beautiful view through the French doors that open to the patio area. The patio features a large lounge area and outdoor dining, as well as a grilling area poolside. The primary suite is conveniently located near the p
Oak Bluffs 8141
Don't miss out on this amazing vacation opportunity on Martha's Vineyard! You can relax in the comfortable living room and enjoy the beautiful view th... Read More
Don't miss out on this amazing vacation opportunity on Martha's Vineyard! You can relax in the comfortable living room and enjoy the beautiful view th... Read More
Relax in this nicely updated three-bedroom home located in the quiet neighborhood of Island Grove. The open-concept living room, dining area, and kitchen offer a comfortable and welcoming space for entertaining. The first floor includes a bedroom, an updated hall bath with laundry room. Upstairs, you'll find two spacious bedrooms that share a hall
Edgartown 7825
Relax in this nicely updated three-bedroom home located in the quiet neighborhood of Island Grove. The open-concept living room, dining area, and kitc... Read More
Relax in this nicely updated three-bedroom home located in the quiet neighborhood of Island Grove. The open-concept living room, dining area, and kitc... Read More
A contemporary home featuring mid-century modern decor creates a truly unique atmosphere. The custom details, including tailor-made headboards and a stunning 12 x 4-foot mahogany dining table, enhance the property's natural tranquility. The gourmet kitchen is equipped with dual ovens, a downdraft Zline stove, and a wine cooler, adding a touch of gl
Edgartown 7731
A contemporary home featuring mid-century modern decor creates a truly unique atmosphere. The custom details, including tailor-made headboards and a s... Read More
A contemporary home featuring mid-century modern decor creates a truly unique atmosphere. The custom details, including tailor-made headboards and a s... Read More
A spectacular compound on the corner of South Summer Street and Captain's Walk, a private way which connects South Summer and South Water Streets, and five minutes to Main Street, and all of the best shops and restaurants. Offering five ensuite bedrooms, including a private bedroom and bath in the carriage house, the main house features a large gre
Edgartown Downtown 173
A spectacular compound on the corner of South Summer Street and Captain's Walk, a private way which connects South Summer and South Water Streets, and... Read More
A spectacular compound on the corner of South Summer Street and Captain's Walk, a private way which connects South Summer and South Water Streets, and... Read More
Classic, custom two-bedroom condo in Tashmoo Cove is nestled in one of Vineyard Haven's most desirable locations. The well-kept community features an association pool, tennis courts, and convenient beach access for your enjoyment. Just a short drive away lies the nine-hole Mink Meadows golf course. Upon entering the home, you'll be welcomed by a s
Vineyard Haven 922
Classic, custom two-bedroom condo in Tashmoo Cove is nestled in one of Vineyard Haven's most desirable locations. The well-kept community features an ... Read More
Classic, custom two-bedroom condo in Tashmoo Cove is nestled in one of Vineyard Haven's most desirable locations. The well-kept community features an ... Read More
A taste of Chilmark in Edgartown - Stunning four-bedroom, 2 1/2 bath vacation home in the center of Edgartown Village, on a quiet cul-de-sac that is a 5-minute walk to restaurants and shops in downtown Edgartown. Listen to the bells ring from the Whaling Church, a quintessential part of the magic of downtown, yet with the space and privacy to rela
Edgartown Downtown 42
A taste of Chilmark in Edgartown - Stunning four-bedroom, 2 1/2 bath vacation home in the center of Edgartown Village, on a quiet cul-de-sac that is ... Read More
A taste of Chilmark in Edgartown - Stunning four-bedroom, 2 1/2 bath vacation home in the center of Edgartown Village, on a quiet cul-de-sac that is ... Read More
Stunning Chilmark contemporary home with a pool is situated high up from the water with fabulous views of the North Shore. There are numerous paths to wander in the woods. Privacy, privacy, privacy offered on twenty two acres. Great space in the main house with five bedrooms on the main level and overflow off of the finished family room downstairs.
Chilmark 2060
Stunning Chilmark contemporary home with a pool is situated high up from the water with fabulous views of the North Shore. There are numerous paths to... Read More
Stunning Chilmark contemporary home with a pool is situated high up from the water with fabulous views of the North Shore. There are numerous paths to... Read More
Upon entering the prestigious Field Club development, you will be graced by an exquisitely designed home with a wonderful eye for detail. It is furnished with the finest linens, bedding, furniture and plenty of comfy sofas throughout. The first floor offers a long open floor plan beginning with a chefs dream kitchen of black granite counter tops
Edgartown Katama 7182
Upon entering the prestigious Field Club development, you will be graced by an exquisitely designed home with a wonderful eye for detail. It is furni... Read More
Upon entering the prestigious Field Club development, you will be graced by an exquisitely designed home with a wonderful eye for detail. It is furni... Read More
Beautiful Three-Bedroom Tashmoo Cove Condo - Experience the best of island living in this lovely end-unit condo, ideally situated in the sought-after Tashmoo Cove community. The open-concept floor plan features central air conditioning, granite countertops, and stainless steel appliances, creating a comfortable and contemporary retreat. The first f
Vineyard Haven 916
Beautiful Three-Bedroom Tashmoo Cove Condo - Experience the best of island living in this lovely end-unit condo, ideally situated in the sought-after ... Read More
Beautiful Three-Bedroom Tashmoo Cove Condo - Experience the best of island living in this lovely end-unit condo, ideally situated in the sought-after ... Read More
Immerse yourself in island luxury and play at this spectacular retreat. Designed for relaxation and fun, this home offers multiple spaces to gather—both indoors and out—surrounded by meticulous craftsmanship and upscale comfort. You'll find beautifully detailed paneling, coffered ceilings, custom lighting, and an abundance of natural light that cre
Edgartown 7772
Immerse yourself in island luxury and play at this spectacular retreat. Designed for relaxation and fun, this home offers multiple spaces to gather—bo... Read More
Immerse yourself in island luxury and play at this spectacular retreat. Designed for relaxation and fun, this home offers multiple spaces to gather—bo... Read More
SHORT STAY AVAILABLE! Four night stay anytime between July 5 and July 12. Welcome to your perfect getaway on Martha's Vineyard! This beautifully decorated 3-bedroom, 2-bath home offers relaxation and convenience. Step outside and enjoy the heated saltwater pool, surrounded by comfortable lounge furniture - the ideal spot for soaking up the sun or u
Edgartown 7823
SHORT STAY AVAILABLE! Four night stay anytime between July 5 and July 12. Welcome to your perfect getaway on Martha's Vineyard! This beautifully decor... Read More
SHORT STAY AVAILABLE! Four night stay anytime between July 5 and July 12. Welcome to your perfect getaway on Martha's Vineyard! This beautifully decor... Read More
Stunning Waterfront Retreat - West Tisbury, Martha's Vineyard. This spectacular residence sits on 7.9 acres with over 600 feet of pristine waterfrontage on Jennie's Cove. Designed for modern island living, the main house features a spacious open-concept kitchen, dining, and living area with expansive views of the water.
The main house features thre
West Tisbury 100050
Stunning Waterfront Retreat - West Tisbury, Martha's Vineyard. This spectacular residence sits on 7.9 acres with over 600 feet of pristine waterfronta... Read More
Stunning Waterfront Retreat - West Tisbury, Martha's Vineyard. This spectacular residence sits on 7.9 acres with over 600 feet of pristine waterfronta... Read More
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