Holiday rentals with a pool in Martha's Vineyard

Find and book unique homes with a pool on Airbnb

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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Top Guest favourite

A cozy living area features a light-colored sofa along with two blue armchairs, creating a comfortable seating arrangement. Natural light fills the space through large windows, while an entertainment unit is present with a flat-screen TV. Decorative pillows and a round coffee table enhance the inviting atmosphere.

Home in Oak Bluffs

5.0 out of 5 average rating, 19 reviews

Chic Oak Bluffs Home with Hot Tub, Walk to Town

A chic coastal escape where upscale comfort meets effortless Vineyard charm. Nestled in the heart of Oak Bluffs and just a 15-minute stroll to Circuit Avenue and the beach, this 3-bedroom, 2-bath home is designed with elegance and ease in mind. Enjoy a serene coastal palette, brand new furnishings, a spacious deck for outdoor dining, and generous yards perfect for barbecues, games, and slow summer mornings. This cozy retreat is ideal for families or couples. It's a modern twist on island living!

Top Guest favourite

The expansive pool, surrounded by a landscaped yard, features a vibrant blue surface reflecting the clear sky. Comfortable lounge chairs are positioned alongside, inviting relaxation. A floating inflatable adds a playful touch to the tranquil setting.

Home in Cotuit

4.96 out of 5 average rating, 140 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 6/20-9/15/26. The reviews tell all!

Top Guest favourite

A refreshing swimming pool is surrounded by a concrete deck, featuring several lounge chairs positioned along one side. Umbrellas provide shade near the pool's edge, and a fenced yard is adorned with greenery, creating a serene outdoor setting.

Home in Barnstable

4.96 out of 5 average rating, 27 reviews

Beach Pass Included! Brand New Spa! Central AC!

Welcome to your Italian Villa in the center of Cape Cod! My father, Sal, created this property to make memories that will last a lifetime. What could be better than a secluded yard that feels like a hidden oasis, but is also walking distance or a short drive to tourism? Walk 0.2mi to ice cream and mini golf. Or, drive 10 mins to local beaches, Hyannis Main Street, island ferries, fishing excursions, whale watching, The Cape Cod Melody Tent, the mall, rt 6, Cape Cod Gateway Airport, and more!

Top Guest favourite

The exterior of a charming house is shown, featuring a gray shingle facade and a welcoming covered porch. Lush greenery and ornamental shrubs frame the entrance, while a gravel driveway leads up to the front door, creating an inviting approach.

Home in Oak Bluffs

4.93 out of 5 average rating, 221 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 favourite

A three-story townhome is nestled among lush greenery, showcasing a muted gray exterior. Large windows bring natural light into the living spaces. A patio is visible on the lower level, furnished with outdoor seating, offering a tranquil view of the surrounding landscape.

Townhouse in Oak Bluffs

5.0 out of 5 average rating, 11 reviews

Oak Bluffs Renovated Retreat

Fully renovated for 2025, this 3-bed, 2.5-bath townhome invites you to unwind with a community pool, tennis courts, and direct access to Sengekontacket Pond. Inside, a custom chef’s kitchen, new baths, and luxury furnishings set an upscale coastal tone. The main level flows from a sun-lit living room to dining area / deck, and powder room. The entire second floor is reserved for the primary suite. The walk-out lower level offers two guest bedrooms, a full bath, laundry, and a private patio.

Superhost

An inviting outdoor space is depicted, featuring a spacious in-ground pool surrounded by lounge chairs. String lights are strung across the pool area, illuminating the backyard. A pool house and umbrellas provide additional amenities, while the home's facade is visible in the background.

Home in Barnstable

4.81 out of 5 average rating, 42 reviews

In-Ground Pool Oasis | 5 Min to Cape Cod Beaches!

Stunning in-ground pool HEATED in May, June, Sept only. Pool is opened in May! 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. 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!

Superhost

The exterior of the cottage features a well-maintained lawn with lush green trees in the background. A wooden deck extends from the house, along with patio chairs overlooking a tranquil pond surrounded by vibrant flowers and plants.

Cottage in Centerville

4.89 out of 5 average rating, 107 reviews

The Holly Cottage

Welcome to Centerville, enjoy this fully equipped 1 bedroom 1 bath home with an easy walk or ride to just about everything. Enjoy the nearby ocean and beaches, or take a ride downtown to Main Street for dining and entertainment. Only a short distance to the ferries for a day trip to the islands and you can be back in time to catch a concert at the Melody Tent. Enjoy your days by the pool and your evenings grilling out on the large deck or chatting with the koi fish.

Superhost

An indoor pool area features large windows and skylights that allow ample natural light. A tropical plant in a pot is positioned in the foreground. The pool is surrounded by a spacious deck with seating options, providing a relaxed environment for enjoyment.

Home in New Bedford

4.73 out of 5 average rating, 222 reviews

Poseidon's Palace - 2.0

Poseidon's Palace is a beach house just steps away from East Beach. Home boasts an indoor pool, all brand new stainless steel appliances, indoor electric fireplace ,sauna . Bring your family along to enjoy holidays, birthdays, weddings , family reunions. Home is on the corner lot of a serene neighborhood with lovely neighbors all around. The home can be a great refuge while you work from home & is ideal for entertaining . Tons of day activities to participate in.

Top Guest favourite

Condo in New Seabury

4.97 out of 5 average rating, 178 reviews

New Seabury Cape Condo | Pool & Beach Escape

Top 5% of Air Bnbs! Welcome to your coastal getaway at The Mews in New Seabury, Mashpee—a refined Cape-style condo tucked within an intimate golf course community. This exclusive enclave of just 15 residences offers a peaceful, private escape with access to a shared association pool reserved solely for residents. Enjoy nearby beaches like South Cape Beach State Park and Mashpee Town Beach, both just minutes away, for the perfect Cape Cod retreat.

Guest favourite

An aerial view of a spacious property featuring a uniquely shaped heated saltwater pool surrounded by a stone patio. A large deck is positioned next to the pool, with several lounge chairs arranged nearby and greenery framing the area.

Home in New Seabury

4.94 out of 5 average rating, 48 reviews

Coastal Charm New Seabury: 5BRs with Private Pool

Welcome to our sunny 5-bedroom New Seabury home! Perfect for families, we offer an open layout, full kitchen, and coffee bar. Relax on the deck, enjoy our fire pit, or swim in our heated saltwater pool (open mid-May to Oct). We’re just 5 mins from South Cape Beach and close to Mashpee Commons and the Popponesset Marketplace. Come make memories in our little slice of Cape Cod paradise! We’d love to host your next getaway!

Guest favourite

An inviting in-ground pool is situated within a meticulously maintained grassy area, surrounded by trees. The pool area features slate-like patio stones and is complemented by six lounge chairs organized neatly under a shaded umbrella.

Home in Edgartown

5.0 out of 5 average rating, 23 reviews

Modern & Spacious Edgartown Home with Pool

Enjoy your vacation in this wonderfully charming three bedroom home with an in-ground heated pool. Head to the beach or stay at home and go for a swim in your own backyard. There is plenty of dining room & deck space to entertain. The bike path and bus shuttle are at the end of the road (a two minute walk away). Downtown Edgartown is less than two miles away for you to enjoy shopping and multiple dining choices.

Top Guest favourite

An aerial view reveals a spacious bay front home surrounded by lush greenery. A large pool is visible in the backyard, with steps leading down to a beach area featuring kayaks. The residence is set in a tranquil, wooded environment.

Home in Cotuit

4.96 out of 5 average rating, 28 reviews

ShoestringBayHouse, waterfront & pool in Cotuit

September: FIVE (5) night minimum stay. August: SEVEN night minimum stay Welcome to ShoestringBayHouse, waterfront on Popponesset Bay. It's all about the views. Our home overlooks the pool, beach and bay. We include: 2-Bikes, 2-Kayaks, and a Barnstable beach pass with beach chairs. Pet friendly and spacious with 4 BR/ 4.5 baths is priced for six adult guests plus children. Pool closes: Columbus Day