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
An aerial view of a spacious backyard features a heated pool surrounded by a grey stone patio. Lounge chairs and umbrellas are positioned around the pool. The house showcases multiple large windows and a deck, with green grass and trees creating a private setting.
Home in Plymouth
4.88 out of 5 average rating, 25 reviews

Mansion with Heated Pool Near Ocean

Welcome to one of Plymouth’s largest vacation homes, offering 4,000 square feet of comfortable living space and a heated pool for summer relaxation. The open floor plan provides plenty of room to unwind, whether you’re enjoying a meal together or lounging by the pool. Why You’ll Love It - Every room has its own bath — rare for a house of this size. - A truly large home with space for up to 12 guests (breakout space for kids/teens + adults). - The heated salt-water pool and expansive pat

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 6/20-9/15/26. The reviews tell all!

Top guest favorite
A modern outdoor space is highlighted by a fresh salt-water pool surrounded by sleek lounge chairs and umbrellas. The pool area is complemented by lush greenery and well-maintained landscaping, offering a serene ambiance for relaxation.
Home in Edgartown
4.97 out of 5 average rating, 33 reviews

Edgartown Designer Retreat With Pool & Hot Tub

Located in Katama, this 3,000-square-foot home has undergone a complete renovation, and offers privacy and easy access via bike path to downtown Edgartown and South Beach. Everything is brand new. There is a salt water heated pool & hot tub! Highlights include 8 inch wide white oak flooring, a custom marble vanity, ultra thick quartz countertops, custom lighting, high end art throughout, all new high end appliances and designer furniture, outdoor shower, gym, and 4 bedrooms / 3.5 bathrooms.

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
4.77 out of 5 average rating, 35 reviews

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

Stunning in-ground pool HEATED in May, June, Sept, Oct 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!

Top guest favorite
A modern home with light grey siding is featured in the background, surrounded by landscaped gardens. A heated saltwater pool, with clear blue water, is framed by grey stone paving. Lounge chairs and shaded seating are situated beside the pool, enhancing the outdoor space.
Home in Mashpee
5 out of 5 average rating, 19 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.

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.

Guest favorite
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 Barnstable
4.93 out of 5 average rating, 100 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.

Top guest favorite
A private deck is showcased with outdoor furniture, including a round table and chairs. A colorful striped umbrella provides shade, while surrounding greenery and flowers add a natural touch. The deck is well-lit by sunlight, creating a warm and inviting space.
Apartment in Hyannis
4.9 out of 5 average rating, 144 reviews

Great Location. Near Beach & Main Street. Unit M1

Our home-away-from-home accommodations include this charming studio with lawn space, a private deck with outdoor furniture and a gas grill. The cottage is comfortably furnished and features a small kitchen. This cottage has a queen bed and a table with sitting area. The kitchen is nicely updated with updated with beautiful granite countertops and stainless steel appliances including an stove/oven, microwave, mini-fridge, toaster, coffee maker. Keurig, and kettle.

Superhost
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, 168 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 3500 sq ft home, 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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