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Holiday rentals with a pool in Martha's Vineyard

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

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Guest favourite
A spacious backyard is highlighted by a large solar-heated pool, surrounded by a stone patio with lounge chairs and umbrellas. The well-maintained house is framed by lush trees and colorful foliage, creating a peaceful outdoor retreat.
Home in Barnstable
5 out of 5 average rating, 6 reviews

CapeSearenity-Large Pool-Beach Passes-Family Fun!

Visit Cape SeaRenity–a stunning home w/solar heated pool and outdoor lounge, perfect for a memorable family vacation and a fabulous Cape Cod experience. Escape to Cape SeaRenity—a beautifully updated home near Barnstable Village with a pool, outdoor lounge, & stylish interiors. Minutes from beaches, shops, dining, & whale-watching. Enjoy a modern kitchen, game-filled garage, bikes & kayaks. With thoughtful design & ProHost® support, it’s the perfect base for exploring Cape Cod with your family.

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 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 favourite
A charming two-story house is featured, with a light gray exterior and blue front door. The inviting porch is furnished with wooden rockers, surrounded by manicured shrubs and vibrant pink flowers. Windows are symmetrically placed, creating a balanced, welcoming appearance.
Home in Falmouth
5 out of 5 average rating, 24 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!

Guest favourite
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, 56 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.

Guest favourite
Home in Tisbury
5 out of 5 average rating, 5 reviews

Modern Family-home,POOL with lots of outdoor space

Staying in this spacious Martha's Vineyard home is extraordinary. With its modern structure, in both the main and guest house, not to mention the patios, and decks full of greenery and flowers. Enjoy the houses perks, check out the brand new hot tub, fire pit and outdoor grill! You'll love making memories with family and friends with all our outdoor accessories, like the showers and dining area (right next to the grill). And if your feeling extra active, enjoy a workout in the guest house gym.

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, 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!

Top guest favourite
An inviting outdoor area features a heated in-ground pool surrounded by a wide patio of pavers. Sun loungers are positioned near the water, and a dining set is shaded under an umbrella. Lush greenery is visible in the background, providing a sense of privacy.
Home in Mashpee
5 out of 5 average rating, 7 reviews

49 Clover Lane, 3 beds, 3.5 baths, pool & firepit

Custom built home, nestled in the heart of the Popponesset. This exquisite property has a heated in-ground pool, surrounded by a spacious patio and gas fire pit. The pool, (seasonal) boasts a motorized cover, and a gas fire pit. The kitchen is complete with a central island, connected to the living room and breakfast area. Spacious bedrooms, fireplaced living room, with large screen TV. Experience the ultimate Cape Cod lifestyle, and a quick stroll to the Popponesset Inn and Marketplace.

Guest favourite
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.
Apartment 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.

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
4.78 out of 5 average rating, 32 reviews

Stunning Cape Home - Inground Pool, 5 Min To Beach

Stunning in-ground pool. 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 favourite
A cozy studio space features sloped ceilings and warm wooden flooring. A spacious bed is dressed in white linens, with accent pillows adding a touch of color. A small kitchenette is visible beside a comfortable chair and a blue rug, offering a relaxed atmosphere.
Guest suite in Dartmouth
4.94 out of 5 average rating, 106 reviews

The Loft @ Beechwood. Private, comfy, coastal!

The Loft is a detached and private studio apartment with a private entrance, beautifully decorated with a coastal decor befitting nearby Padanaram Harbor & Village. The skylights and a 'really, really comfortable bed' will help you relax and enjoy all the area has to offer. Ideal for two guests, but able to accommodate a third, or two children, The Loft is a great home base to explore the local area or the Islands of Cuttyhunk, Martha's Vineyard & Nantucket.

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
4.95 out of 5 average rating, 22 reviews

ShoestringBayHouse, waterfront & pool in Cotuit

June 3,4, 17 &18 are $99/night Welcome to ShoestringBayHouse, waterfront on Popponesset Bay. Our home overlooks the un-heated pool (opens May 15th), beach and bay. We include: Bikes, Kayaks, and a Barnstable beach pass. Pet friendly and spacious with 4 BR/ 4.5 baths is priced for six (6) adult guests. (other options available). Guest is solely responsible for carefully reading and understanding the rental property description.

Top guest favourite
A welcoming living area features a comfortable sectional sofa and two wooden armchairs arranged around a circular coffee table. Natural light fills the space, highlighting a large area rug on the hardwood floor. A well-equipped kitchen is visible in the background.
Apartment in Mashpee
4.97 out of 5 average rating, 164 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).

Popular amenities for Martha's Vineyard rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favourite
A private backyard features a large swimming pool surrounded by a patio with stone paving. Lush greenery and low shrubs border the area, while a wooden table and chairs are positioned nearby. The house is visible in the background, framed by trees.
Home in Mashpee
4.91 out of 5 average rating, 22 reviews

Beautiful Mashpee Home with Pool

Top guest favourite
A saltwater pool is set within a stone patio area, surrounded by lush greenery. Lounge chairs and a shaded table with a red umbrella offer comfortable seating options. The serene view of Morey Pond is visible beyond the pool, framed by trees under a clear blue sky.
Home in Plymouth
4.97 out of 5 average rating, 65 reviews

Our families slice of heaven

Superhost
Home in Barnstable
4.88 out of 5 average rating, 40 reviews

Beachside Retreat pool&spa bball court

Guest favourite
An outdoor pool area showcases a heated inground pool with clear water, surrounded by a wooden deck. Sun loungers are placed nearby, and patio umbrellas provide shade. Lush greenery and trees line the background, offering a serene environment. A beach ball floats in the water.
Home in Mashpee
4.97 out of 5 average rating, 29 reviews

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

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

Superhost
A light-filled living area features comfortable seating with blue and white accents. A natural wood coffee table sits in the center, surrounded by a cozy area rug. A separate dining space is visible through an open archway, showcasing a charming dining table and decorative elements.
Home in Plymouth
4.74 out of 5 average rating, 69 reviews

Tranquil Home with Pool, Fireplace, and Game Room

Guest favourite
A charming Cape-style house is surrounded by lush green grass, featuring a well-maintained front yard adorned with flower beds and small American flags. The entrance is highlighted by a decorative door with a wreath, framed by neatly arranged bushes. A single-car garage is visible on the right.
Home in Mashpee
4.85 out of 5 average rating, 65 reviews

Sunny Cape w/Private Pool, Steps to Private Lake

Guest favourite
The exterior of a spacious home is depicted, featuring a peaked roof and well-manicured landscaping. Lush green shrubs and blooming hydrangeas frame the entrance, while a driveway leads to a two-car garage. A flag decorates the front, conveying a welcoming environment.
Home in Falmouth
4.87 out of 5 average rating, 31 reviews

Sippewissett Forest Magic by the Sea

Apartment rentals with a pool

Guest favourite
A spacious pool area is enclosed by a white fence, surrounded by lush greenery. Lounge chairs are positioned around the edge of the inviting water, with trees and houses framing the scene in the background. The sky transitions to soft hues during sunset.
Apartment in Vineyard Haven
4.96 out of 5 average rating, 24 reviews

Relax....You're on Island Time......

A spacious living area features a large dark leather sectional sofa with decorative pillows. The room is illuminated with natural light and displays coastal-themed artwork on the walls, adding a relaxed atmosphere. A sliding barn door is visible, contributing to the modern design.
Apartment in Falmouth
4.83 out of 5 average rating, 18 reviews

Falmouth MA, Cape Cod Getaway

A clear swimming pool is surrounded by well-maintained grass and tall, green trees. Several lounge chairs are positioned around the pool's perimeter. A colorful float is visible in the water, and a shaded area is indicated by a large umbrella. The overall setting is peaceful and inviting.
Apartment in Falmouth
4.65 out of 5 average rating, 51 reviews

Lovely lakefront studio/condo with pool

A cozy living and dining area features a light-colored sofa with decorative throw pillows, complemented by a wooden dining table surrounded by four chairs. A fireplace, framed art, and a warm-toned lamp enhance the space, while a patterned rug adds a touch of comfort.
Apartment in Oak Bluffs
4.67 out of 5 average rating, 3 reviews

Island Inn - Two Bedroom Suite - 1A - Oak Bluffs,

Superhost
An aerial view captures the resort's layout alongside the coastline. Sandy beach stretches along the water's edge, while the Atlantic Ocean meets a calm bay. Behind the resort, residential areas are interspersed with patches of greenery, illustrating the natural beauty surrounding the location.
Apartment in Falmouth
4.63 out of 5 average rating, 8 reviews

InnSeason Resorts Surfside

A relaxing outdoor pool area features lounge chairs arranged along the pool's edge. The surrounding building, showcasing spacious balconies, houses multiple units. Guests enjoy sunbathing and walking nearby, with clear skies overhead enhancing the scene.
Apartment in Falmouth
5 out of 5 average rating, 4 reviews

Two bedroom condo .on the water Falmouth, ma

A community pool is surrounded by a tan deck and green lounge chairs. The pool features clear blue water and a ladder for entry. Lush greenery provides a natural backdrop, with a few buildings visible in the distance, emphasizing a peaceful environment.
Apartment in Mashpee
4.94 out of 5 average rating, 16 reviews

5 Mi to Mashpee Commons: Coastal Mashpee Condo

The exterior of a cozy blue condo is shown, surrounded by green grass and trees. A wooden fence and picnic table are visible in the foreground, as well as a large tree with budding leaves. The building features multiple windows with white shutters.
Apartment in Tisbury
4.78 out of 5 average rating, 23 reviews

Martha’s Vineyard Condo * Near Ferry

Other holiday rentals with a pool

Superhost
A cabin with a light green exterior is framed by lush trees. Four adirondack chairs surround a stone fire pit set on a grassy area. A charcoal grill is positioned nearby, and a spacious deck is visible at the rear of the cabin.
Cabin in Falmouth
4.56 out of 5 average rating, 9 reviews

Cape Cabin, Pools, Hot Tub, Beach, Game RM, & More

Top guest favourite
The charming exterior of the newly renovated home is highlighted by a sloping roof and a welcoming front door. Framing the entrance are neatly trimmed bushes and a small pathway leading to the door. A garage is located on the side, complemented by grassy green surroundings.
Home in Falmouth
5 out of 5 average rating, 23 reviews

Home in Falmouth ~ 5 min drive to beach

Guest favourite
A sunlit space features large glass windows providing views of the surrounding greenery. Two sofas, one with textured fabric and the other adorned with cushions and a throw, are arranged around a wooden coffee table. Natural light enhances the welcoming atmosphere.
Home in Edgartown
5 out of 5 average rating, 8 reviews

Sunny condo with pool, central to beach & town

Superhost
An in-ground pool glistens under the sky, surrounded by a spacious patio. A two-story house with dark blue siding is visible in the background, along with lounge chairs arranged neatly. Lush green vegetation frames the scene, creating a secluded atmosphere.
Home in Bourne
4.75 out of 5 average rating, 4 reviews

Cozy Cape Cod House - Stroll or Bike the Canal

Guest favourite
The exterior of the home is surrounded by lush greenery and features a spacious deck. A retractable awning provides shade over the seating area, while the charming wooden siding and multiple skylights add character to the structure. The clear blue sky enhances the inviting atmosphere.
Home in West Tisbury
5 out of 5 average rating, 11 reviews

West Tisbury Gem with Deck + Association Pool

Superhost
Two cozy cabins are depicted in a wooded setting, each featuring a covered porch with steps leading to the ground. The cabins are surrounded by pine needles and trees, providing a natural atmosphere and privacy for guests.
Cabin in Sandwich
4.69 out of 5 average rating, 13 reviews

Cozy Cape Cod Cabin | Pond, Pool & Pet-Friendly

Superhost
A single-story blue house is surrounded by manicured shrubbery and a well-maintained garden pathway. Windows reflect sunlight, and the entrance features a decorative lamp post. A welcoming front door adds to the home's appeal, framed by neatly arranged greenery.
Home in Barnstable
4.8 out of 5 average rating, 5 reviews

Centerville Pool House

Superhost
An inviting inground pool is surrounded by well-maintained grass and a concrete deck. Loungers line one side of the pool, and steps lead up to a wooden deck area. Lush greenery provides shade and enhances the outdoor ambiance.
Home in Plymouth
4.82 out of 5 average rating, 33 reviews

The Plymouth Pool House

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