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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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
4.76 out of 5 average rating, 33 reviews

Heated Pool Oasis | 5 Min to Cape Cod Beaches!

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!

Top guest favorite
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 Barnstable
4.95 out of 5 average rating, 128 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!

Top guest favorite
A sandy beach extends toward calm waters bordered by a tree-lined shore, creating a serene natural setting. The gentle curve of the waterway leads to a distant point, where lush greenery enhances the picturesque landscape. The bright blue sky adds to the tranquil atmosphere.
Home in Falmouth
5 out of 5 average rating, 23 reviews

Renovated ranch with pool access

Renovated home in E. Falmouth offers endless relaxation and recreation: swim, bike, fish, kayak, walk, lounge. Short walk to Assoc beach or to the Seashores Clubhouse pool (seasonal). Bring your kayak: explore Washburn Island & Waquoit Bay. Sleeps 6 with 1-floor living, AC, laundry, large back deck, and outdoor shower. Nearby, you'll find dining/shopping areas, wineries/breweries, & more. A short drive to Woods Hole offers fast boats to Martha's Vineyard. Book now and enjoy Sandy Feet Retreat.

Guest favorite
An indoor heated saltwater pool is showcased, surrounded by large windows that provide ample natural light and views of the landscaped garden outside. A hot tub is situated beside the pool, and indoor plants add a touch of greenery to the serene setting.
Villa in Mashpee
4.95 out of 5 average rating, 58 reviews

Heated Indoor Pool & Spa - Golf Course View

CHERRY BLOSSOM RETREAT Cold days, raining days and power outage won't hinder your stay at this luxurious home, boasting an indoor heated salt water pool and hot tub fully equipped with a backup generator, overlooking the renowned 3-Hole Championship Golf Course. Our ultimate luxury home features an array of indoor entertainment options including arcades, air hockey, foosball PS5, Switch, etc. comfortably accommodating 6 to 8 guests, and merely a short drive to all all New Seabury's amenities.

Top guest favorite
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, 209 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
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 out of 5 average rating, 7 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.

Top guest favorite
A spacious carriage house apartment is framed by lush greenery and colorful landscaping. The building features a crisp white exterior with large windows, creating a bright atmosphere. The entrance is marked by a stone pathway, leading to an inviting garden area adorned with seasonal pumpkins.
Barn in Falmouth
5 out of 5 average rating, 18 reviews

Falmouth/Woods Hole Carriage House Roost

Welcome to our Cozy Carriage House Apartment located only a few minutes from the quaint village of Woods Hole, Falmouth and the Martha's Vineyard Ferry. We are located in the perfect setting to relax and enjoy all the area has to offer. Come enjoy The Shining Sea Bike path which is 10.7 miles , Sandy beaches, lively restaurants & local music scene, shopping on historic Main Street, Farmers Markets & more. Your sure to fall in Love with " Ole Cape Cod " when you visit our home and area

Guest favorite
A clear blue swimming pool is surrounded by lounge chairs positioned for relaxation. Lush greenery provides a natural backdrop, while a shaded area offers protection from the sun. Steps lead from the pool to a nearby structure, adding convenience for guests.
Condo in Tisbury
4.92 out of 5 average rating, 49 reviews

Private 3bdrm Condo Tashmoo Woods

This 3 bedroom (3 king) 2 1/2 baths newly renovated condo is in a private setting with screened in porch. New kitchen, gas grill on deck, outdoor shower. -Access to the Tashmoo Woods Association pool, tennis courts and play ground. -Close to West Chop beaches. -Two miles from downtown Vineyard Haven. On bus route, but best to have a car. -The primary bedroom (king bed) is downstairs and the 2 upstairs bedrooms share a bath (shower only). Minimum rental 5 days, 1 week in summer.

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Condo in Edgartown
4.8 out of 5 average rating, 5 reviews

Brand New 2BR Condo w/ Pool. No Pets!

This beautifully renovated condo is in the heart of Edgartown. 5 min walk to downtown shops, restaurants, and waterfront. This unit has 2-bedrooms & 1.5-baths. The master has a king bed and half bath, and the second bedroom features a queen bed and full bath. Enjoy a spacious living room with high ceilings, a full kitchen, and access to outdoor spaces with a pool. Sleeps 4, this condo is the perfect base for your Martha's Vineyard adventure!

Top guest favorite
Condo in Mashpee
4.97 out of 5 average rating, 166 reviews

Sleep 6 @ New Seabury w/ Pool Access, All Seasons!

Welcome to Your Coastal Getaway at The Mews, New Seabury – Mashpee, MA Tucked inside the beautiful New Seabury Country Club, our cozy Cape-style condo offers the perfect balance of relaxation and adventure on Cape Cod. Enjoy access to a private condo association pool just a 3-minute walk away, and a beach that is 5 min drive or 10 min bike ride or 30 min walk (walk cuts through golf course-ask host for directions).

Guest favorite
A charming stone exterior features a distinctive arched design, with two red doors providing access to the private studio. Lush greenery surrounds the entrance, complemented by a gravel pathway and neatly trimmed bushes, evoking a sense of tranquility in the outdoor space.
Apartment in Falmouth
4.8 out of 5 average rating, 114 reviews

Falmouth, Cozy Studio Near Old Silver Beach

This private studio is located in a quiet neighborhood. Located on the second floor, it has A/C, a skylight, Dish TV Amenities include a gazebo. The kitchenette includes a microwave, toaster oven and a Keurig coffee maker. The pool is NOT heated and is open seasonally (July 1 - Labor Day) Close to beaches! Please note there is NO STOVE in the unit.

Guest favorite
A spacious colonial house is framed by lush green grass and mature trees. The exterior features dark shingles with multiple windows reflecting natural light. A winding driveway leads to the entrance, while a wooden fence provides privacy at the rear.
Home in Edgartown
4.93 out of 5 average rating, 54 reviews

Beautiful Edgartown Colonial with heated pool.

Stunning 5 bedroom, 10 room, 3500 square foot colonial in beautiful area. Gourmet kitchen, dining room, living room, den, family room with ping pong. Huge deck, private yard with fire pit and outdoor shower. 30 x 16 x 4 heated in ground pool. Central air. Kayaks, bikes. Seven passenger Toyota Highlander available to rent May- October.

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