Holiday rentals with a pool in Edgartown

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.

4.97 out of 5 average rating, 29 reviews

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

~~ You Have Arrived! Welcome to "The Fore Seasons" in desirable New Seabury on Cape Cod. ⛳️🏖🌸☀️ You will be sure to fall in love with old Cape Cod in this 4,500 sqft private home located on the 10th hole fairway of the championship golf course. With its 4 bedrooms, 4 bathrooms, Heated Inground Pool, Outdoor Shower, Putting Green, Ping Pong table and Ctrl Air there is enough room for the largest families. Pool open from Mid-May until through Columbus Day! Available year round for all gathering

4.95 out of 5 average rating, 128 reviews

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

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!

5 out of 5 average rating, 23 reviews

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 East Falmouth

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.

4.95 out of 5 average rating, 56 reviews

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 New Seabury

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.

4.93 out of 5 average rating, 209 reviews

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

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!

5 out of 5 average rating, 7 reviews

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 Popponesset

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.

4.92 out of 5 average rating, 49 reviews

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

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.

4.78 out of 5 average rating, 32 reviews

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

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!

4.8 out of 5 average rating, 5 reviews

A bright living room is showcased, featuring white sofas and a light wood coffee table. A decorative shelving unit lines the wall, filled with various items. Large windows allow natural light to fill the space, and soft curtains frame the view of the outdoors.

Apartment in Edgartown

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!

4.95 out of 5 average rating, 22 reviews

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

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.

4.97 out of 5 average rating, 164 reviews

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 New Seabury

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).

4.86 out of 5 average rating, 107 reviews

An inviting living space is highlighted with a grey sofa, modern dining table with four chairs, and bright windows allowing natural light. The kitchen has sleek cabinets and appliances. Below, the scenic Keyes Memorial Beach is shown with soft sand and a sunset. A community pool featuring turquoise water and lounge chairs is also visible.

Flat in Hyannis Port

Cute Cottage Near Beach & Main Street 3BR/3BA (15)

Stay at a charming 3-Bedroom cottage in a beautiful setting within walking distance to Cape Cod's warm sandy beaches and Main Street Hyannis. Captain Gosnold Village is ideally located within a short walk from three of the Cape's best beaches and nestled between picturesque Hyannis Port and the vibrant atmosphere of Hyannis Harbor with its island ferries, sightseeing and fishing charters.

Popular amenities for Edgartown rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 15 reviews

A charming single-story home is presented with a neatly manicured lawn, adorned with blooming blue hydrangeas. A flag is displayed on the front porch, and large windows provide a view of the inviting interior. The clear blue sky complements the home's fresh appearance.

Home in Hyannis Port

Renovated Cape Oasis W/ New Pool and Game Room!

A spacious deck features a wooden dining table with matching chairs, overlooking a private heated pool and serene water views. Lush greenery surrounds the area, while a private dock is visible along the shoreline.

5 out of 5 average rating, 7 reviews

Waterfront Home w/ Dock, Heated Pool, Kayaks & A/C

4.91 out of 5 average rating, 22 reviews

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

Beautiful Mashpee Home with Pool

4.85 out of 5 average rating, 65 reviews

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

Sunny Cape w/Private Pool, Steps to Private Lake

4.87 out of 5 average rating, 31 reviews

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

Sippewissett Forest Magic by the Sea

5 out of 5 average rating, 26 reviews

An in-ground pool is surrounded by a spacious patio, featuring several blue lounge chairs. Lush greenery frames the area, with a clear blue sky overhead. The pool’s water reflects the sunlight, creating a refreshing ambiance for relaxation and entertainment.

Home in Hyannis Port

Hyannis Port Coastal Escape – Pool & Walk to Beach

5 out of 5 average rating, 24 reviews

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 North Falmouth

New Construction Home with Pool in N. Falmouth

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.

4.91 out of 5 average rating, 34 reviews

Home w/ golf view, salted heat pool, mins to beach

Apartment rentals with a pool

Apartment in Vineyard Haven

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.

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

5 out of 5 average rating, 8 reviews

A two-story building designed in a classic Cape Cod style is showcased, featuring a large balcony on the front. Lush green landscaping surrounds the building, enhancing the tranquil outdoor setting. Nearby structures are visible, displaying similar architectural features.

Apartment in Falmouth

Beachside Villiage-Oceanfront

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,

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 New Seabury

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 Vineyard Haven

4.78 out of 5 average rating, 23 reviews

Martha’s Vineyard Condo * Near Ferry

4.69 out of 5 average rating, 32 reviews

The entrance of the condominium is shown, featuring a wooden exterior with shingles. A pathway leads to the door, surrounded by neatly trimmed shrubs and grass. Bright sunlight highlights the clear sky and the inviting pathway.

Apartment in Falmouth

Condo in Falmouth MA

Apartment in Vineyard Haven

A bright living area features a navy blue sectional sofa and a wooden dining table with four chairs. Light streams in through a large window adorned with green curtains, complementing a coastal-themed wall art piece. A cozy area rug lies beneath a wooden coffee table.

4.72 out of 5 average rating, 25 reviews

Heart of VH, w/ac, pool & harborview

Other holiday rentals with a pool

A private backyard features a heated pool surrounded by a spacious deck. The contemporary two-story home, with large glass windows and doors, provides views of the lush greenery. Lounge chairs and umbrellas are arranged for outdoor relaxation.

5 out of 5 average rating, 27 reviews

New Seabury pool/hot tub near beach,Popponesett

4.75 out of 5 average rating, 24 reviews

A serene outdoor space features a heated in-ground pool surrounded by multiple wooden lounge chairs. The cottage exudes a charming aesthetic, with a combination of shingled siding and large windows. Lush greenery provides privacy, and a deck area offers additional seating near the water.

Home in West Yarmouth

Delightful 6 Bedroom with Private Pool Near Beach

The kitchen features a bright white color scheme with modern high-end appliances. An island with seating for four is highlighted, alongside a view of the outdoor patio through large glass doors. Light wood flooring complements the space, enhancing its expansive feel.

Home in East Falmouth

5 out of 5 average rating, 4 reviews

Summer 2025 Open!Walk to Great Pond, central a/c

Serviced apartment in Falmouth

A swimming pool is visible with several lounge chairs arranged around it. The ocean can be seen in the background, along with a small gazebo. A clear blue sky complements the scene, enhancing the resort's coastal atmosphere.

4.91 out of 5 average rating, 11 reviews

Ocean Front Resort Studio Unit

4.91 out of 5 average rating, 55 reviews

Private POOL*New Seabury* 3 bedroom

A dining area features a wooden table surrounded by black spindle-back chairs, positioned on a blue and white chevron rug. Natural light streams through windows adorned with light blinds, illuminating the room's neutral walls and highlighting a small vase of flowers atop the table.

Home in West Tisbury

5 out of 5 average rating, 3 reviews

WestTisbury Charm, Carroll House

5 out of 5 average rating, 11 reviews

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

West Tisbury Gem with Deck + Association Pool