Vacation rentals with a pool in Edgartown

4.97 out of 5 average rating, 29 reviews

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 New Seabury

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

A communal pool area features a clear blue pool surrounded by concrete decking. Lounge chairs are arranged neatly on the sides, with greenery visible in the background. A wooden fence encloses the area, providing a private atmosphere.

4.91 out of 5 average rating, 115 reviews

Sea Salt Studio - Steps to Glendon Rd Beach

Funky studio (Unit #1) only 175 yards from a white sand beach on Nantucket Sound. Soak up the sun at the beach, relax by the pool or enjoy a relaxing cocktail on your own private patio. This studio is equipped with a fridge, microwave and gas stove as well as a fully stocked kitchenette and cable/Roku TV. A futon couch offers extra sleeping space, if needed. Outside, enjoy a natural gas grill. Walk or bike to multiple restaurants, ice cream shops and all the amenities Dennis Port has to offer.

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.

4.95 out of 5 average rating, 57 reviews

A spacious wooden deck is surrounded by trees, offering a serene view of the natural landscape. A small round table with drinks is set between two folding chairs. A gas grill is positioned against a wooden railing, with sunlight filtering through the foliage.

Apartment in Barnstable

Studio Apartment

Private Studio Apt on lower level of owner occupied House.Private deck overlooking Pond. Queen bed, single sofabed/and small sleeping loft. Very comfortable for 2 people but can sleep up to 4. Kitchenette w/dinnerware and cookware. Coffee maker, fridge, microwave, toaster oven, outside gas grill. Private bath/shower. TV, WiFi, A/C. Pond access, SUP, kayaks. Pool/hot tub on Main House level available for use on request. Sunrise view. Golfcourses, shopping, restaurants, beaches nearby.

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.

Condo 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.

4.93 out of 5 average rating, 100 reviews

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

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.

Apartment in Hyannis Port

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.

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.

4.97 out of 5 average rating, 172 reviews

Condo in New Seabury

New Seabury Cape Condo | Pool & Beach Escape

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.

4.87 out of 5 average rating, 15 reviews

The lighthouse features a round white structure topped with a lantern room. A spacious deck wraps around the building, accompanied by a well-maintained lawn and a decorative pumpkin. American flags are displayed, and the surrounding area includes additional nearby structures and views of the water.

Home in West Dennis

Jolly Captain Lighthouse

Ever wanted to stay in a lighthouse?! Well this your opportunity. The Jolly captain lighthouse was originally built in 1960 and recently renovated in 2024-2025. Including breathtaking views of Bass River. Access to community pool is available. In addition, dock slip is available for additional cost. Please contact host privately for additional information.

Apartment in North Falmouth

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.

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.

4.93 out of 5 average rating, 54 reviews

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

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.

Popular amenities for Edgartown rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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

5 out of 5 average rating, 7 reviews

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.

Home in New Seabury

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

Home in Edgartown

Spacious 5BR Home w/ Pool & Two Living Areas

5 out of 5 average rating, 14 reviews

An outdoor seating area features gray cushioned sofas arranged around a dark table. Surrounding trees provide a natural backdrop, while colorful potted flowers add a vibrant touch. The area extends towards a pool visible in the background, enhancing the inviting outdoor atmosphere.

Home in South Yarmouth

Fenced Pool, Fire pit, Outside dining, Coffee bar

4.82 out of 5 average rating, 17 reviews

A heated saltwater pool glistens under the sun, surrounded by a spacious paver patio. The fenced backyard provides privacy, while a light-colored house with a deck offers a welcoming ambiance. Lush trees stand in the background, enhancing the serene outdoor space.

Home in Barnstable

Centerville Oasis, Heated Saltwater Pool!

5 out of 5 average rating, 27 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

4.69 out of 5 average rating, 52 reviews

A spacious bar room features a wooden bar with four high chairs, complemented by a comfortable seating area with a light grey sectional sofa and a round coffee table. Natural light fills the space through skylights and large windows, with an American flag hanging on the wall.

Home in Mashpee

The Wakeby esCAPE ~ Pool & Walk to Beach!

4.96 out of 5 average rating, 28 reviews

A spacious two-story home is set against a clear blue sky, surrounded by well-maintained green lawns and mature trees. The property features a welcoming front porch and ample landscaping, providing a serene outdoor environment. A guesthouse is visible in the background.

Home in Falmouth

Secluded Cape Cod home in Falmouth with pool

Condo rentals with a pool

A spacious sleeping area features a large bed with neutral bedding and colorful accent pillows. A TV is mounted on the wall. Natural light filters through a sliding glass door, which opens to an outdoor area with a small table and chairs.

4.82 out of 5 average rating, 74 reviews

Cozy Studio Just Steps Away From the Beach!

4.96 out of 5 average rating, 24 reviews

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.

Condo in Vineyard Haven

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

A light-filled living area features a cozy sofa layered with a soft throw, accompanied by a stylish coffee table. The calming wall art depicts ocean waves, while lamps provide additional lighting. A door leads outside, and a chair adds a pop of color.

4.93 out of 5 average rating, 44 reviews

1BR 2nd Floor Condo with pool

The spacious living area features a queen-sized bed and a comfortable sofa. A dining table with two chairs sits near the window, allowing natural light to brighten the room. Simple decor includes star-shaped wall accents, enhancing the relaxed coastal ambiance.

4.84 out of 5 average rating, 87 reviews

Comfy Cape Escape! Spacious, Cozy, Close to Beach!

The studio features a spacious bed adorned with colorful decorative pillows. A seating area with a small table and golden chairs is visible. Light pours in through sheer curtains, complemented by three framed art pieces on the wall, adding character to the bright space.

4.88 out of 5 average rating, 75 reviews

Stylish & Modern Studio Condo - Steps to the Beach

A wooden sign is displayed on a light-colored wall, featuring the phrase 'Heaven is a little closer by the Beach' in white lettering on a teal background. The sign is framed in a rustic white border, enhancing its coastal charm.

4.85 out of 5 average rating, 61 reviews

Hidden Hideaway

A serene pool area is visible, featuring clear blue water under a sunny sky. Poolside loungers are arranged for relaxation, while the two-story condo building with balconies lines the background. Lush greenery and trees enhance the outdoor space.

4.97 out of 5 average rating, 60 reviews

Mary's Cape Escape

A sandy beach extends along the shoreline, gently lapped by calm waves under a clear blue sky. Small groups of people can be seen enjoying the beach, with the distant landscape of grassy dunes and beach vegetation providing a natural backdrop.

4.86 out of 5 average rating, 58 reviews

Mid Cape Cod, 3 Season Haven by Bass River

Other vacation rentals with a pool

5 out of 5 average rating, 8 reviews

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

Sunny condo with pool, central to beach & town

Apartment in Hyannis Port

A light and airy living area is highlighted by soft blue walls and nautical decor. A futon with a blue and white cover offers additional seating, paired with a small round table and chairs. A potted plant adds a touch of greenery to the space.

4.87 out of 5 average rating, 60 reviews

1 bedroom apartment located 5 minute walk to beach

4.91 out of 5 average rating, 11 reviews

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.

Apartment in Falmouth

Ocean Front Resort Studio Unit

A private swimming pool is surrounded by a spacious wooden deck and sun loungers. The mid-century home features large glass doors that connect the indoor space to the outdoor area. Lush greenery and trees provide a peaceful backdrop, while a bright umbrella offers shade.

Home in Chilmark

4.54 out of 5 average rating, 24 reviews

Iconic Mid-Century Home with Gorgeous Ocean Views,

5 out of 5 average rating, 7 reviews

A paved outdoor seating area is visible with several round tables and chairs arranged to provide views of the water at sunset. The sky features warm hues of orange and purple as the sun dips below the horizon, with the ocean beyond and neighboring houses in the background.

Apartment in Dennis Port

Steps to the Beach & Heated Pool!

4.98 out of 5 average rating, 100 reviews

The exterior of the cottage is shown, featuring a shingle-clad façade. Two tall windows frame the front door, while well-maintained shrubs line the path. Sunlight casts gentle shadows on the manicured lawn and surrounding trees, creating a serene outdoor setting.

Cottage in Edgartown

Lovely two - story private cottage. Katama quiet!

5 out of 5 average rating, 13 reviews

A layout of a travel trailer is displayed, featuring a camper queen bed at one end and a dinette that converts into additional sleeping space. The kitchen area includes a stove, fridge, and sink. A compact bathroom and bunk beds are also present, providing efficient use of space.

Camper/RV in Falmouth

Cape Cod Getaway Travel Trailer at Sun Retreats!