Vacation rentals with a pool in Martha's Vineyard

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Top-rated rentals with a pool in Martha's Vineyard

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Superhost

Home in Barnstable

4.8 out of 5 average rating, 20 reviews

Stunning Cape Home - Inground Pool, 5 Min To Beach

Stunning in ground pool HEATED in May, June, Sept, Oct only. Just 5 minutes from Craigville, Dowses and Covell's Beach! Perfect for mid-size groups or families, this home sleeps 8 and boasts a dreamy, private, fenced-in backyard w/ a, pool house w/ TV & bar, outdoor shower, and cozy patios. Complete w/ all your beach essentials. Conveniently located, we're 13 minutes from Mashpee Commons and 10 minutes from local grocery stores, local bakeries& restaurants. Central to all the Cape has to offer!

Guest favorite

Home in Yarmouth

4.9 out of 5 average rating, 42 reviews

Winslow Acres [heated] Pool Escape; pool May 15

Pool Open 5/15 Escape to the Cape at this beautifully maintained home with lovely seasonal heated pool (heated spring/fall). Hot tub available all year. Make s'mores and memories year-round at the fire pit table. 4 bedrooms and 2.5 baths (2 showers) plus an outside shower May through October. Plenty of room for up to 8 people - sorry, no parties - (plus pets - fee applies)! Only 3 miles to beaches. The ferry to Nantucket and Martha's Vineyard is not far, and a great addition to any Cape trip!

Superhost

Home in East Sandwich

4.92 out of 5 average rating, 64 reviews

Large Home Heated Swimming Pool Private Beach

Perfect for extended-family fun in this stunningly built home (3300 sqft) with 5 bedrooms and 4 bathrooms. First-floor shower. Walk 1000 feet to a private beach with full access rights. Along the beach, you can stroll further east to Sandy Neck Beach. Open kitchen, dining and great rooms are perfect for entertaining! Swim in the ocean or jump right into a beautiful 16x40 heated fiberglass pool with pool lights! Hosted by an extremely experienced host who's committed to making your stay perfect.

Top guest favorite

Home in Barnstable

4.95 out of 5 average rating, 113 reviews

Private Pool, near beaches, 3 BR/3 BA, Central Air

Enjoy the Barnstable historic seaside village of Cotuit in this sprawling house with central air, nestled in the pines on a quiet street with private gated (unheated) pool, lg. backyard, firepit, ample parking, just blocks from Main St, Ropes Beach, scenic ocean views, fort playground, and Kettleer baseball. Each bedroom has a TV and ensuite bathroom! Relax in the seasonal sunroom overlooking the pool; grill burgers on the patio. Max. 9 (6 adults). Pool open 6/20-9/15/24. The reviews tell all!

Superhost

Home in Dennis

4.63 out of 5 average rating, 30 reviews

House on Cape Cod with pool close to beach

This single family house is located at the end of a cul de sac in a quite neighborhood in walking distance to Mayflower and Bayview beaches. You enter through the bright and open kitchen, looking out over the patio and the pool. The open living and dining room open up to a sun room where you can relax after a fun day at the beach. The two smaller bedrooms share a big bathroom with tub and double sink, whereas the master bedroom has its own bathroom. A big dining table can host up to 8 people.

Top guest favorite

Home in Plymouth

4.97 out of 5 average rating, 32 reviews

Getaway with pool

Look no further! This stunning beach house offers everything you need. Situated on a quiet street on Cape Cod Bay, it is very close to area beaches and ponds. The outdoor space is perfect for entertaining and includes lap pool, three decks, patio and fire pit. The downstairs includes living room, family room, bedroom, full bath, eat-in kitchen, and enclosed porch overlooking the backyard. The second floor features 4 more bedrooms, 2 baths, laundry room, and en suite primary bedroom with deck.

Guest favorite

Home in Falmouth

5 out of 5 average rating, 13 reviews

New Construction Home with Pool in N. Falmouth

Come relax in this new construction house, located in quaint North Falmouth. Decide to spend the day at home and hang by the pool and hot tub. Have the kids ride their scooters around the cul de sac while you watch the sunset on the front porch. If you decide to venture out, Old Silver and Megansett Beaches are approx. 2 miles away, and the Shining Sea Bikeway is at the end of the street that takes you all the way to Woods Hole. Whether you stay in or go out, living is easy with this rental!

Top guest favorite

Home in Oak Bluffs

4.94 out of 5 average rating, 194 reviews

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, ENDS 9/1) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

Guest favorite

Home in Mashpee

5 out of 5 average rating, 12 reviews

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

This home was custom built in 2022, and is designed to provide comfort, luxury and loads of charm for the discerning vacationer. New construction with a nod to the Nantucket Sea Captain's houses of yesteryear. Professionally decorated and landscaped, offering every amenity you could possibly desire; from an in-ground, heated, saltwater pool (with electric cover), hot tub, outdoor shower, fire-pit, and even a cabana with a sink, refrigerator, and smart TV. Just a 3 min walk to private beach.

Superhost

Guest suite in Barnstable

4.92 out of 5 average rating, 25 reviews

Cozy 1-bedroom cottage with pool and beach access

Cozy apartment within short walking distance of a gorgeous private beach on the bayside of Cape Cod. The gentle bay is perfect for families. Walk the flats during low tide or float in the gentle bay waters. Later relax by the outdoor pool. Or take a walk on the Mass Audubon Long Pasture Wildlife Sanctuary trails. Note: this private apartment is attached to owner's residence but has its own private entrance and parking spot. IN SEASON RENTAL: SATURDAY TO SATURDAY unless approved by host

Guest favorite

Home in Mashpee

5 out of 5 average rating, 11 reviews

Cape Gem in New Seabury with private heated pool

Our Pristine, Newly Renovated, Patio home with Private heated Pool, located in the Mews of New Seabury, offers the privacy and peacefulness for the perfect vacation. The sandy local beaches—South Cape Beach and Popponesett—are both very short drive away (5-10 minutes)! Highlights of the seashore resort community of New Seabury: Mashpee Commons (fine dining, shops, movie cinema), golf courses, boating, walking trails, close proximity to ferries to Nantucket and Martha’s Vineyard.

Superhost

Home in Sandwich

4.64 out of 5 average rating, 11 reviews

New Cape Escape for 10 People With Heated Pool

This spacious 4-bed, 3-bath newly renovated retreat with a two-car garage and ample parking is designed for the ultimate getaway. Entertainment options abound with a dedicated poker room, complete with a stylish bar, and a delightful kids playroom on the lower level. Step into the backyard oasis with a salted heated pool, fenced for privacy, creating a perfect space for outdoor enjoyment. This dog-friendly haven is tailor-made for large families or multi-family vacations.